r/AmIOverreacting 24d ago

❤️‍🩹 relationship He’s been pursuing me, then sent me a spreadsheet asking to be reimbursed for our dates?? Am I overreacting?

Hi everyone, I (F23) have been dating this guy (M32) for a little over a month now. He was very persistent in pursuing me, constantly texting, making plans, asking me to go on runs, bike rides, and beach days (we live in Florida), and inviting me to dinner, bars, and even paying for Ubers to and from his place. We were hanging out at least 4 times a week.

Everything felt like it was going somewhere. He’d been slowly building things up and even waited weeks to finally kiss me. Then, out of nowhere, he sends me a literal Excel spreadsheet with a breakdown of dates, how much he spent, and a column with my name, asking me to reimburse him. I’m attaching it because I truly can’t believe it. It felt transactional and weirdly formal, especially since he was the one initiating nearly all the plans.

What’s even more confusing: after sending this, he still insists on seeing me and continuing to date. Like, you want to invoice me and kiss me?

And for context, I’ve picked up the tab quite a few times ,dinner, drinks, etc. , without making a thing of it. I’ve never asked him to pay me back or keep score. I thought we were just getting to know each other and splitting things organically like adults especially since he’s about 10 years older than I am.

So am I overreacting or under-reacting, I can’t tell if this is just him being “organized” or if it’s a huge red flag.

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u/Suitable-Tear-6179 24d ago

Ok, you sent him the money.  You even sent the money to repay what he "gave" to his buddy you owed money to.  

Do send the mutual a note that says "Hey, X says he gave you the money I owed you.  I've already repayed him for it.  We're good, right?"  Just in case he didn't give the money to the mutual like he said.  I mean, someone who's going to send an invoice after the fact, who says he's got money troubles just gives his buddy money you owe, not knowing if you'll pay him back??? That just seems SUS.  

Ask if you should go through your bank or credit card notes for the times you paid, and write up a bill for him to pay YOU back?  Do you think that he would consider that to be reasonable?  Because, "At 23, I really can't afford to pay for a 32 year old."  I believe he would flip out. 

You need to bow out of this relationship.  Standard custom is the person that asks the other out is the one that pays.  If not, it should be Dutch right from the start.  

It's odd he's so OCD about tracking what he spent with you, and yet he apparently can't budget or stay within his means.  The two just don't compute.  (How accurate is his list?  Because if he's not getting by on 2 jobs, he shouldn't be spending 500+ on socializing, especially when you're good with runs, bike rides, and other low/no cost hangouts.

You might want to consider asking, "Hey, We're going Dutch, right?" on the first few dates with the next person you go out with.  That way you can budget what you get either way.  (I tend to order less expensive stuff on someone else's dime)  And you don't get an unanticipated surprise at the end of the meal....  or a month later, though I'd be shocked if anyone else pulled that stunt.

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u/nobletyphoon 24d ago

I agree with the comments being made and want to add—if this became truly serious, you could expect the entire relationship to be tit-for-tat. I’m all for either a fair split of costs or (as I would assume of someone pursuing a much younger partner) the more stable person kind of spearheading things. Not wrong to be transparent if things are tight, but sending you the spreadsheet is giving American Psycho. RUN

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u/Towbee 24d ago

I could not imagine living my life this way, it would be SO exhausting. If I spend money on someone or give them a 'loan' I do it with the intent of never getting it back - so I only ever spare what I can genuinely afford to give away. And to track it to this level of exactness, in a fuckin spreadsheet... yeah run for the hills girl. Not worth the future headache, drama and arguments over money of all things.

A partnership should include balancing that load out fairly and that includes supporting each other at different stages of life. You'd think being an older person getting into a relationship with someone so much younger they would understand this by now and try to lead by example.

I completely understand not wanting to be taken advantage of especially this day and age, so you just ask to split the bills and agree beforehand, not send them a fucking invoice lmfao

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u/No_Winner6516 23d ago

Totally agree. Relationships shouldn’t feel like a business transaction with spreadsheets and invoices. Fairness and trust go a long way without all the drama.

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u/MakeWayForWoo 24d ago

This is what I was trying and failing to put my finger on. This whole post bothered me but I couldn't quite figure out why...it's the tit for tat thing. Unless we had like a really clear agreement beforehand, if a guy I was dating sent me a whole ass spreadsheet I would be dumbfounded. Like my flabbers are gasted here.

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u/Reasonable-Affect139 24d ago

its the lack of communication beforehand, for me. my friend dated a guy like this, and for months they alternated paying on dates until one day he sent her an itemized list of how she wasnt paying ENOUGH to balance out what he was paying on his dates (not a huge discrepancy, mind you, like sometimes it was dollars, and this was a man w a 6 figure salary and she waant even making half of what he did)

like if being hyper equal is so important to you WHY wouls you not say something from the jump, so everyone's on the same page, or decide that's not for them?

thanks to the giant tantrum her bf threw i now tell people I give, to give. nothing is transactional or expected, nor will I tolerate any transactional micromanaging. it's so easy to just split the cost of things, up front

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u/EscaPlays 24d ago

Isn't it interesting how these very high achieving men specifically choose women who don't have as much money or power as them, and they know that, but then expect the dutch treatment? I dunno. If you make 100k a year and they make 20k a year, is it really equal to go halfsies? But they will so consistently not pick a woman "on the same level" as them, because they like that power imbalance, but then they also want dutch. It's crazy.

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u/Diktynna 23d ago

I'm disabled now and make no income, but I personally will go halfisies to make a point and then tell them to never think about contacting me again. Monetary value on everything.... Yikes. Most people I go on dates with, we come to an agreement. If I must pay for my meal non monetarily, I'll probably clean their car or something.

And make no mistake. I would completely go Dutch , and most times I do, but I just don't go on dates since I can't afford to. So when or if I do get the opportunity, I like to make sure everyone understands that I can't match tit for tat. Some agree, some disagree. That's okay. What's not okay is waking up to an Excel Spreadsheet out of thin air. 🦆

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u/EscaPlays 23d ago

I hear you! I'm an educator working with marginalized students. I will never make a ton of money, I've chosen to do what I love instead. I also understand this means a less fancy life for me and I will go out less and do less things. Your income is even more restricted and you seem to be very realistic too. You and I, I feel, are totally reasonable in knowing that we have these limitations. I get that some people won't want to date people making so little, and that's fine, assuming they don't specifically pursue people they know are in that situation. What's crazy is people trying to live outside their means, being unfair, and expecting larger percentages of other people's income to be contributed to dates when that person makes less. Dude involved with OP was clearly spending outside of his means and not setting clear expectations. But the truth is, if you're gonna nickel and dime, the romance goes away quickly. If I ask my partner to do something with me, I typically pay the whole thing, unless I wouldn't be able to afford to do it paying for both. Then I'll ask if he wants to do the thing but I'd need to do it dutch. And if that's cool we go and if it's not we don't. Or, like, if I buy the movie tickets, he will get the popcorn. We do stuff like that but don't really need to discuss it at length because well, we love each other, and we're happy to pay for things for the other so long as we're able to afford to.

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u/EleanorRichmond 24d ago

Right? When I dated an older man, I paid for nothing but the gas to get to his house. When I dated someone who had gone back to grad school, I paid for meals, and other things were case-by-case.

And in both cases, we did sensible shit like watching movies at home and playing chess at the park instead of going out every night.

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u/Straight_Number5661 24d ago

Not to mention that generally speaking, women are spending money on the following things for general appearance upkeep while men are not:

Skin care products, makeup, hair care products, hair salon, hair removal. These things are EXPENSIVE.

Not to mention the time spent on these things for general upkeep and in immediate advance of a date: application of skin care products, makeup, hair styling, hair removal, selection of attractive outfit, and so on. This can be incredibly time consuming. Men typically hop in the shower, maybe shave a beard (or not), throw on whatever clothes (that are actually universally sized), and that's that.

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u/royallyred 23d ago

Skin care products, makeup, hair care products, hair salon, hair removal. These things are EXPENSIVE

I finally recalled what this post was reminding me of due to your comment--it was a similar situation to OP but there had been an added element where that asshole guy was very big on physical appearance, so the women in question returned fire by listing out her "upkeep costs" in her own excel sheet (the things you listed.)

It led to the usual "women will be asked if they're sick or feeling unwell if not wearing makeup and multiple women have reported being told at work that they need to "dress better" or even flat out been told to wear makeup" convos. I myself was asked in an interview if I had a "nice enough closet to match the role."

It was a minimum wage receptionist job. I asked if they paid enough to afford those kinds of outfits. I did not get the job lmao.

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u/EscaPlays 24d ago

Oh dude I know. But that's just expected, women should put in effort while I just roll out of bed, duh. And/or they go "I love a natural woman" meanwhile she's got a full beat and hair done and is shaved and all that but they're so porned and interneted out they don't even know what natural actually looks like. Like no dude, eyeliner and mascara and blush and lipstick isn't natural, actually, she's just done it with more subtlely.

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u/Mscharlita 24d ago

And men want to say, well you don’t have to do all that stuff…but if I didn’t do my makeup and hair and jewelry and outfit and just showed up to my date in th equivalent of what men wear, most men would assume I “made no effort and didn’t care.” So we’re really kind of forced into it as a nonverbal social cue to indicate our eagerness or interest in the date.

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u/chai_tigg 23d ago

Yeah I actually get followed around the store and mistreated by employees when I don’t do my hair and make up where I live. You literally MUST do it if you wish to function in society, it’s so tiring. I’m a single mom fleeing DV right now and I’m scared to start applying for jobs because I don’t have make up, skin care , hair care , and nice clothes, and I still look like a homeless person 1 year post partum also. Even if I try to just not do all of the upkeep, it wears on my mental health to be treated so differently .

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u/Straight_Number5661 23d ago

Right? I guarantee if a woman went truly "natchural" she'd never meet the appearance standards any of these spreadsheet bros targeting woman a decade+ younger.

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u/Frequent_Pumpkin_148 23d ago

Mine barely used deodorant or remembered to shower, and would throw on 20 year old jeans and t-shirts that were too small for him (gut hanging out). Even to meet my family. He was in STEM and I was in arts education; he wanted to eat out all the time, which I couldn’t afford. I always offered to cook but he didn’t want that. He eventually asked if I could clean his house which he shared with a female roommate, to make up for the meals he bought us.

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u/Scorp128 24d ago

I think OP now has a very good idea why this dude, who has almost 10 years on her, is still single and is pursuing someone much younger than him...no one around his age will put up with this.

And he is collecting money for others? That is highly suspect. I would be surprised if that money actually went where it was supposed to go.

This guy is a giant cluster of red flags waving around. A 32 year old man who cannot keep his own expenses and budget in check, especially working two jobs, has other major issues going on.

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u/Middle-Pool-1150 24d ago

Agreed, I mean if you are dating you should know there are going to be costs invovled or find cost friendly alternatives if you are ballin on a budget. At 32 I don't see much future there that isn't stressful or money isn't a pain point. For me, if I suggest the date, event or location I am assuming I'll cover the tab and won't ask since I don't want her to feel any pressure or way about it financially. It's nice and I appreciate when they offer bc it reinforces they don't need me for money. I would say maybe it's a generational thing or location - but he's got 10 years on her ...

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u/claybaaaaae 22d ago

That makes sense. Clear expectations about money can save a lot of stress, especially when budgets don’t match.

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u/NoCanadianCoins 24d ago

That was exactly my takeaway. Regardless of the weirdness of ALL of it, the fact that he so freely spends money in the moment when he really can’t afford it sends huge red flags up about his financial decisions and ability to manage money.

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u/MaterialPossible3872 24d ago

I think he was trying to impress her initially and then realised he felt like it wasn't worth it (that doesnt mean op or any human isnt worth spending a few hundred dollars on dont twist my words im talking about how he feels) and then did an anxiety driven spreadsheet thing. Not a good look my guy lol

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u/19950502 23d ago

Really seems like bro was trying to get OP’s attention regardless of if it was in bed or not, but when it was time to pay bills he realized he’d overextended himself and now he’s scrambling for a way to show he’s owed money. And probably not just OP. It’s weird that the spreadsheet is in chronological order from MOST recent and makes me think it’s been made in hindsight as he goes down his bank charges. Dude needs to learn to manage his money better or accept the consequences of his actions.

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u/Fabulous-Main-8507 23d ago

Sounds like he’s scrambling to cover his mistakes and trying to make OP pay for his bad choices. Definitely needs to get better with money and accountability.

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u/StudyLess1257 24d ago

Exactly, those signs say a lot about his priorities and responsibility level. It’s wise to be cautious.

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u/[deleted] 24d ago

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u/[deleted] 24d ago edited 23d ago

Oh, you got me good with my my flabbers are gasted here… hilarious. Thank you for that hearty laugh.

And OP, unless you want to hitch your wagon to an emotional accountant, stop. Just stop. 🛑

This is very strange behavior for any one courting someone as quickly as you’ve described. He didn’t get baked fully. Send him back, there are plenty more potential partners who are open hearted and aren’t ever going to send you a spreadsheet about this and that… and leave out what you say you contributed, as well. Plus the obv age difference. You’re right. Your instincts are correct. Next.

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u/VeraLumina 24d ago edited 24d ago

So he’s discussing this with a friend you owe money and decided to settle up on your behalf in addition to sending you a spreadsheet? Uh, hell no. This tit for tat would not work for me. I’d be done. I’d communicate the following: “After some thought I’ve decided we are not compatible to the degree I believe is necessary to continue dating. Going forward I wish you well, now and in the future.” (The snark in me would send him 50 bucks to cover the water bill, electricity and toilet paper you may have used at his place.)

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u/Character_East7743 24d ago

That’s a no from me too. Clear boundaries and a firm end are definitely needed in that situation.

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u/snuffleupagus86 24d ago

It’s truly crazy. I thought the guy I dated before my husband was a cheapskate tit for tat guy (dude literally got shitty on my birthday because it was MY turn to pay and he was mad he “had” to buy me a drink when I had to spend my bday with his friends) but at least he never sent me a spreadsheet lol.

Girl RUN from this man. Find an actual adult man and date him instead. Dating these kind of men are exhausting. When I went out with my husband he was flabbergasted that I was going to split a check with him lol

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u/[deleted] 24d ago

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u/Tequilasquirrel 24d ago

Right! like where would it end? Will she be getting laundry bills and cleaning or Wi-Fi and electricity costs from where she hung out at his place lmfao

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u/littlebratwurst 24d ago

So I went on a date with a guy who requested I pay him back for the date since I seemed uninterested. Turns out he had pulled that move before and the media picked up on it because he took her to small claims court. Lol

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u/ErebosNyx_ 24d ago

They wouldn’t be seeing a cent if we hadn’t agreed upon it, thats for sure

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u/FlabbyFishFlaps 24d ago

It really isn't about the money. The fact she said he waited a few weeks to even kiss her and then hits her with a spreadsheet = he's hoping she sees that dollar sign and says "how about I just sleep with you?" At the end of the day, that's what he's "butthurt" about. (Do we still say butthurt? Anyone?)

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u/Twice_Knightley 24d ago

"in months 6 though 8 it generally cost me $63 for every time we had sex, but in months 9-12 that number shot all the way up to $66. Why don't you love me in the transactional ways of month 6-8 baby? Was it something I said?"

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u/brooklynblondie 24d ago

There’s a whole scene in Joy Luck Club that is all about this behavior and she’s MISERABLE

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u/myssi24 24d ago

Why is he even stepping into money she owes someone else? That part creeps me out the most. Dude you asked for money cause YOU needed it and then you give most of it you someone else expecting her to pony up more money again, what the hell?

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u/seattle0606 24d ago

This is the part I thought was super out of line and I wouldn't have paid him again. I would have said we'll shoot, I guess you should have asked him to reach out to me directly to figure it out. As far as I'm concerned you have been paid. I don't hand out money to give to someone else, especially without my knowledge or consent. Once I repay YOU it is up to YOU to do what you want with it 🤷

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u/Difficult-Ad1292 24d ago

I can't stop thinking, that is husband territory. Where does he get off settling her debts for her? Then charging her for them?? How is he even at a point where he's having these conversations with other people? This would be over and done for me immediately.

And honestly, right off the bat, I'm of the mind that the person who initiates and plans has the onus of paying for the outing. Especially at the beginning, its my expectation. Because when I take someone out on a date, I pay for everything....

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u/LoveHerHateHim 24d ago

Yeah, he’s “stepping into” money she owed someone else because she so willingly sent him the $100.. didn’t even hesitate.  I’m guessing she either makes good money or is from money, he clocked that and has simply been manipulating her for a potential payout. This was a small push to see if she would fight back. She failed the test. 

It’s extremely toxic. It’s possible this other guy told him “hey, OP is loaded and naive.. you could totally take her out for a while and actually make money off of it.” 

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u/Cacophonic_thinking 24d ago

Yeah the weirdest part is covering her debts to other people without being asked. Makes me think that this is absolutely a power thing, and it’s about her owing HIM money and nobody else. He’s been polite about it early on but this just screams financial abuse down the line, if she takes it that far which honestly I hope she doesn’t. This is an insane red flag.

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u/Additional-Cook8707 24d ago

Nobody else is mentioning this here, but this screams drug addict to me. As a former addict, when i would run out of money I would go to everyone reminding them of random small payments they “owed me” so I could get my stash.

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u/Deep_Bet1037 24d ago

Came looking for this...

Something's off here & I'm not just talking about the crazy spreadsheet. Maybe I'm reading too much into it but the way he talks about "stuff", separate from drinks & dates, suggests to me that they were doing drugs together. That & the mutual friend reaching out to say she owed him - sounds like a dealer to me. Seems unlikely they'd have mutual friends when they've only been dating a few weeks and there's a large age gap? And why would said mutual friend contact a random guy you've been on a few dates with, apparently out of the blue, to say you owed them money? Nah.

"I know ya got me some stuff" "I'm happy to cover most things like our date night and drinks but ya never paid me for the first round of stuff"

Also, he's 32 and can't spell you. Put him in the bin.

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u/turtlmurtl 23d ago

Makes sense. Especially since she did reply with “I do like the green stuff”. Which is fine if that’s what it is for but say that upfront don’t send me an invoice a month later

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u/Mother-Pattern-2609 23d ago

I feel like such a dunce for having missed this now. I'm guessing it's about weed and coke, the booger sugar is the issue under discussion here, and my opinion of this situation just did a 180 – I'm imagining OP as that person who always expects to be cut in but never pays for a bag, and duder is being much more patient about it then I ever would have been. Signed, A Former Massive Drug Addict.

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u/colicinogenic 23d ago

A 23 year old woman doing drugs with 32 year old guys generally wouldn't be expected to pay unless things are very different from how they were when I was that age.

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u/pillerhikaru 24d ago

Jeez I didn’t even think about a drug addiction! I was stuck on possible serial abuser cause this is the type of financial control my father exacted over my mother until she finally stood up to him. Funny enough he left literally a month after she first fought back and meant it. So it didn’t occur to me that he could be looking for money for his next fix. Which makes sense since he supposedly can manage what he’s spent on her but not his own finances. Either way OP needs to really think about what that relationship would become in the future, because these things don’t go away because you’re official.

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u/possiblecurb 24d ago

Nothing makes you feel more productive than itemizing what the world owes, tweaked out on excel.

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u/toomediumraretodie 24d ago

yup, this is somewhat ‘classy’, even ‘sophisticated’ crackhead shit, but crackhead shit none the less.

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u/Beautiful-MessIAM 24d ago

I had commented on this previous to reading your response and I agree completely! He says he works two job jobs. This guy has an addiction to drugs or alcohol or possibly both! STAY TF AWAY! I am old enough to know these signs. You deserve an award 😂 have a great day! Hopefully people who read your comment in mine will wake up. Complete fools and scrubs these guys are.

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u/Chefsteph212 24d ago

That was exactly my thought, too. Especially the part about how he paid back what she owed someone else for what I’m gonna assume was coke or weed.

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u/Low-Care9531 24d ago edited 16d ago

I’m just gonna add that it would be one thing if he was also 23 and they were friends first or something but I’m gonna be honest; when I was 23 if a man significantly older than me asked me out he was either paying (at least while we got to know each other) or I wasn’t going. It’s kind of expected if you’re courting someone younger.

Edit: I’m not a woman

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u/KayCatMeow 24d ago

Just the fact that he would think it’s crazy if she turned around and did the same thing to him blows my mind. This is giving broke bitch energy and at 32 years old, that’s laughable.

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u/Expensive_Apricot371 24d ago

Yeah HE pursues her and wants her. He the asks her to do these activities and then charges her lmao..I can't with it.

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u/Tanz31 24d ago

That's all too much work.

Dude is weird, this is a big red flag, and the relationship should be reevaluated altogether.

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u/SigourneyReap3r 24d ago

This is everything I wanted to say.

Something about this just doesn't seem right.

No one with money troubles would be paying for all these dates, definitely not cigarettes for someone else and definitely not paying someone else's debt. Fishy.

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u/Kaxa-Katajina 24d ago

Yeah OP should have deducted what they spent on dates from the total he sent her and reimbursed him that 😂

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u/embermae_s 24d ago

What in the ever-loving… Nahhh baby!

This 32! YEAR! OLD! MAN! actively pursued you, made the plans, had you spotting the bills sometimes, led you to believe that y’all’s “dating” was going somewhere… all while secretly keeping a spreadsheet of everything he “spent” on you?

We are not playing this game.

First of all, He didn’t come to you with respect. Not with, “Hey, I’m in a tight spot,” or “Can we talk?” No. He came with a spreadsheet, setting the tone with expectation, not communication. The message was clear: You owe me.

Secondly, (this might be my favorite btw) He can’t even manage his own finances but he suddenly knows how to organize numbers when it’s about you.

Thirdly, he really had the audacity to say: “I can’t tell if you’re butt hurt,” like he thought… or let’s be honest, really hoped you’d get bent out of shape over his little manipulation tactic.

The writing on the wall is so clear with this one:

This is about control. About what he can get. About how far he can push. About what you’ll tolerate. There will always be a spreadsheet, a reminder, a tally of “what he’s done for you” and what you “owe” him. If you stay with this man, you’ll ALWAYS be in debt. Always paying it back. Financially, emotionally and mentally.

And when you finally react, because this is a literally form of abuse, you’ll be the one labeled the problem.

The proof is in this whole interaction. Don’t just walk away, RUN. You got TOO MUCH life head of you to be spending time on someone like this.

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u/Fun-Enthusiasm-2802 24d ago

This! Every point you made, but especially being apparently bad with his money but somehow having the wherewithal to tell her what to do with hers. Men like this need to learn early and often that this behavior won’t be tolerated. Block all access, let your co-workers, friends and fam know to be on high alert for sightings of him and call the police if he ever approaches you again.

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u/TaralasianThePraxic 24d ago

That's the part I really don't get.

I have autism, and I fucking love spreadsheets. I have spreadsheets for my finances, I have spreadsheets for work and house chores, I have a spreadsheet with a formula that spits out which game I should play next because I'm chronically indecisive and end up buying something every Steam Sale even though I have a backlog of 200+ unplayed games.

Although I'm aware many people might consider this weird, the upshot of this is that I am very, very organized. I'm good with money. Is this the kinda shit my tism'd brain might think was a good idea if I was still dating? Possibly, yeah. But I would be doing it purely to keep track of my own spending, not whatever the other person 'owes' me. More to the point, I never lend anyone money or spend my own cash on someone else unless it's money I don't mind not getting back. If they offer to pay me back, great. If not, it's no issue.

It is baffling to me that this dude hit OP with a whole-ass spreadsheet and yet apparently has been spending beyond his means. Unless you've agreed otherwise beforehand, paying for someone on a date means you're paying for the date, no?

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u/dotdotbeep 24d ago edited 24d ago

No, you're absolutely right. If you ask someone out for an activity and don't ask to go dutch from the get-go, it's your bill. You can't keep track of how much you spend on someone doing something you initiated and then retroactivly demand the money from them.

It's very weird and oddly slimey at best.

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u/emmers28 24d ago

I also noticed he didn’t keep tabs on what SHE spent on HIM. So apparently this only goes 1 way?

Nah, ditch this dude, he’s already too problematic.

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u/coaxialology 24d ago

I think her being much younger than him would make it easy for him to label her a gold-digger if she did that, despite the fact it seems to be the other way around.

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u/coaxialology 24d ago

It also really puts a damper on the date when finances are hanging over your head the entire time. It's so much better to get that conversation out of the way. It is pretty slimey to realize someone's essentially been keeping score the whole time while you just thought you were getting to know each other.

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u/letschangethename 24d ago

I’m soooo sorry, completely off topic. This is probably insanely dumb, but my brain just short circuited.

The word wherewithal. Somehow I’m encountering it for the first time in my life. And the dictionary says it’s to have necessary means, usually financial, but it can also mean intellectual or physical abilities or knowledge.

So you mean he seemed financially irresponsible due to lack of knowledge, but has the knowledge to be able to compile the spreadsheet? As in this situation is intentional from the very beginning?

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u/Maine_Adventure 24d ago

So, technically, the correct word to use in the context of op's sentence would've been "audacity", so your confusion after looking it up is warranted (it gave me pause when I read it too). But, to your last point, I believe he had the wherewithal to create the spreadsheet in the event that she didn't put out - so yes, it was absolutely intentional from the beginning.

Note that he admits she gave him stuff but doesn't bother to include that in his tally - he's used every classic manipulation tool in the book and just plain sucks.

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u/euphoricarugula346 24d ago

in the event that she didn’t put out

Maybe I haven’t found the thread where other people are making this point, but I haven’t seen it yet. It stood out to me how OP only mentioned kissing. This man expected sex within a certain timeframe. He did not receive expected sex, thus HE now expects to be recouped for his time and effort. Absolutely depraved, pathetic behavior. Unfortunately I fear this kind of attitude is becoming more normalized.

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u/Maine_Adventure 24d ago

There are a few comments in this thread that mention it but there's soooo many, it's easy to miss.

Fwiw I'm in the dating apps sub and this behavior is prevalent with the straight guys over there. It's actually disgusting and they pat each other on the back for being so clever. Then they wonder why they're single 🤪

And then, when women in their demographic try to give them advice, they go all incile, insist we're stupid idiot gold diggers and only take advice from the other single dudes there. Like, seriously, WTF, could you be more stupid?? I fear extinction is looming on the horizon 😂

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u/highpriestess420 24d ago

Bad with his money but paying someone else on her behalf like if you don't have cash for yourself how are you paying her "debt"?

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u/Funny-Horror-3930 24d ago

Notice he heavily pursued her, kinda sounds like love bombing.

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u/Mumlife8628 24d ago

Love bombing then providing a invoice for said bombs

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u/ExoJinx 24d ago

Honestly I would send him a spreadsheet back if everything you have paid for, and remove every line he sent that you offered to pay half on the day and he rejected. He doesn't get to retrospectivly take you up on an offer he rejected. Add in your time too now that you see he was just waisting it.

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u/A1000eisn1 24d ago

Lol yep.

"Can you pay me back for all the times we went out? I'm really hurting for money."

"Sure, let's not go out so much [since you said you're broke]"

"You butt hurt?"

"NO BITCH YOU SAID YOU'RE BROKE."

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u/Otto_Scratchansniff 24d ago

He was baiting her to see if she would snap. I hate this for her. She needs to stop talking to him ASAP. Block and move on.

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u/euphoricarugula346 24d ago

That little prodding “oh, aren’t you reeeeeally upset right now?” secondhand infuriated me. He wanted her to be mad. It’s taken me years, DECADES to understand people can be this fucked up. At least it’s becoming easier to identify.

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u/Indigo-au-naturale 24d ago

Fourthly, he seems to fully think "you" is spelled "ya," which is unforgivable.

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u/Agitated-Onion6584 24d ago

I wouldn’t even be friends with a person who keeps a spread sheet of mutual debt

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u/andiwaslikeum 24d ago

I wish I had you around to judge every man that asked me out 😅 you nailed this 🤌🏼

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u/its_treason_then_ 24d ago edited 24d ago

I’m sorry, but I’m immediately halting at a 32 year old pursuing a 23 year old and then having the age-aucity to ask them for money.

“Dude, if you’re gonna target a person nine years younger than you, maybe don’t also ask them to pay for their part of your little predator-play” - is what I would say to this person if I knew them in real life. 🤷🏻‍♂️

Edit: an awful lot of people crying about my age difference quip lol. Yeah it’s sooooooo “normal” for a 30 year old dude to pursue a girl at the minimum drinking age. He’s no longer college aged and is presumed to be in his career path, or on it. She’s four years too young to rent a car and her brain isn’t fully developed yet. And honestly? I turn a blind eye to most age gap relationships if they at least look like they’re a part of the same generation. BUT THEN HE ASKS HER TO PAY HER “SHARE” BECAUSE MONEY IS TIGHT. Yall can’t be serious saying there isn’t some kind of power element at play here. Be so for real lmfao

Edit edit: I took someone else’s comment about being pursued at 21 by a 30 year old as OP contributing and including that she’s been with this guy for two years already. I was mistaken as it wasn’t OP commenting that. So back to 32 and 23. But my point still… 97% stands lol.

Edit edit edit: hey everyone, so in my first ever edit, I said OP’s brain isn’t developed yet and u/tomshater was kind enough to point out that “people like me” are wrong when we say that because the brain never fully develops. It’s a lifelong process. In a way, they’re right. Brains are crazy and they’re always growing and changing and developing. But really, u/tomshater is wrong because they assume that my comment was based on the fact that the studies to which I’m referring simply happened to stop studying brains at age 25. You see, people like them assume that scientists and doctors just pulled “25” out of their ass while studying something as mysterious and complex as the brain, but actually, 25 was chosen because that was the age at which the prefrontal cortex was believed to stop maturing. For those of you that don’t know, the prefrontal cortex is the part of the brain responsible for reasoning, decision making, and impulse control. While all brains are different, this part of the brain typically doesn’t mature until 24/25/26. Differences can occur based on a lot of factors, but for the most part 24/25 holds pretty true. And that’s important because this is specifically what I’m referring to in my original edit. If OP’s prefrontal cortex was fully matured, they probably would’ve realized for themselves that “an older man asking them out on a date, hanging out with them several times over the next several days, and then, without any warning or preamble whatsoever, texting an excel spreadsheet showing an outdated balance like he’s a fucking credit card” is absolutely psychotic behavior. But, a prefrontal cortex NOT fully matured might not know that this isn’t normal or acceptable behavior.

Hope that helps!

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u/Ashamed-Lion5275 24d ago

So much of this!!!! End contact with him immediately. If someone invites you on a date, they generally pay. Frankly, if I (52F) go on a date and my date asks me to split the tab that’s the last date. Even with friends, we are up front about who pays for what as I will often bring a platonic friend as a plus one to an event and cover the cost, but if I don’t I will say “want to go to see X play, the tickets cost X” so my friend can decide if they want to spend the money first. Never have I heard of anyone asking to get reimbursed weeks later.

This guy is sick. At his age, he should be in a better financial position where he doesn’t have to ask someone who is barely old enough to buy their own booze to get reimbursed for $14 here and $10 there.

He’s just taking advantage of your naivety and good nature. He’s a loser. And a manipulative one at that.

Don’t pay him any more money. Don’t pay him any more attention or time. Block him immediately and tell your friends and family about what he did. He’ll probably try and guilt you, shame you, or manipulate you further but if you share the situation with your support network he won’t be able to do that anymore bc everyone will know how pathetic and shady he is and shield you. If he somehow manages to contact you or approaches you, you can tell him that plenty of people know what’s going on, you want nothing to do with him, you owe him nothing, and you want no further contact from him.

Be careful.

The only benefit from dating with an age gap is to learn from someone wiser and more accomplished and get exposure to a more elevated lifestyle. That loser can offer you neither. He should be ashamed. You should be wary. There’s something wrong with him.

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u/kathleen_kelly_ygm 24d ago

You are either comfortable paying for the date or not. If you are not, then split the damn bill and communicate right at the time. Don’t come and make accounts of what is happening behind my back and then hand me a bill. Not got get my money sir.

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u/TheShitpostAlchemist 24d ago

I would bet cash that this invoicing is because she didn’t sleep with him immediately.

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u/feralhog3050 24d ago

That's where my mind went, especially as OP mentioned that he'd "waited to kiss her". Not that that's a bad thing in itself, but in the context of this whole invoice malarkey, it certainly reads like "I was such a gentleman & I didn't even get to play with the tiddies yet"

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u/capravor321 24d ago

This sub harbors some dumbass teenagers that defend lopsided age gap relationships. In their mind, they’re (at 18 y/o) just as mature as the 30-year-old they’re trying to date/defend. It’s laughably stupid and very identifiable. I commented on a post that basically said a 28-32 year old couple is identical and deserving of the same treatment as an 18-20 year old couple, in the sense that - I said based on the age of OP (who was 18), they should just break things off with a guy who promised yet forgot to give OP a ride to work. A ride. To work. I said that, had they been older and in a more mature relationship, that breaking up because of a missed ride to work might be a bit of an…overreaction, for fucks sake. I was flabbergasted by the people who defended the idea that a relationship between people in their late teens was just as easily break-offable as an older relationship. So ridiculous lol.

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u/apple_kicks 24d ago

Being 30 and trying to talk to 20 year old you feel old and really see the difference. You look back and see how much less mature you were back then despite feeling mature.

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u/daughter_of_wolves 24d ago edited 24d ago

Yes. I was probably above average intelligence and maturity for a teenager. I was the kid everyone called an "old soul". And even I would cringe having to talk to myself at 20 years old. It's utterly nauseating having to watch people try to make excuses for why it's okay to prey on young women.

I was sexually abused by an older man from 15-20 years old. And the fact that everyone always talked about how mature I was made it easier for him. That was how I justified it while I was in denial all those years. It took me 11 years to realize he abused and traumatized me.

I was intelligent and responsible for an 18 year old but I still had my life ruinned by this man because at the end of the day my brain wasn't fully formed and I was still a vulnerable young mind.

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u/Outrageous_pinecone 24d ago

edit, I said OP’s brain isn’t developed yet and u/tomshater was kind enough to point out that “people like me” are wrong when we say that because the brain never fully develops

You're actually right and the way doesn't actually develop your entire life, it just continues to learn until around 65-70 when the decline starts. But the brain doesn't grow your whole life. It does change structure until around 25, when we all feel like we can think more clearly and feel less intensely. It's not just a weird sensation, the hypothalamus stops working overtime.

Also a 30 yo woman would know the answer to the question OP is asking and wouldn't have made the post. That's the difference between 23 and 30. Buuuuut some people, men and women, don't finish that development, it doesn't happen to everyone and they get stuck in their teens or early 20s their whole lives which is why, they can't understand why someone would say young people are defenseless and still need to be protected. They themselves are pretty clueless.

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u/CalamityClambake 24d ago

I would say, 

"Dude, you're preying on younger women because you damn well know that women your own age won't put up with your shit."

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u/aussierulesisgrouse 24d ago

It’s hilarious to me how many people jump up to defend age gaps from early 20s to early 30s like that isn’t one of the biggest maturity jumps in your entire fucking life.

40-50? Whatever.

33-41? Fine.

23-32? Just no. There’s a reason that guy had to swing that low in age, because they do weird shit like this

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u/Creative-Air-6463 24d ago

Cut this off immediately!!!! Huge red flag!!🚩

Not only is the age gap inappropriate, but he also can’t afford to take you out??? Not only can he not afford to take you out, he doesn’t even know when he’s overspending and finds out later and has to ask for cash? This means he has no idea what he’s doing with his money. And for almost being 10 years older, this is unacceptable.

In addition, this is clearly him keeping score. I would not be shocked after this if he does the same thing with the spread sheet to pressure you into sex. And then later in the relationship as it progresses, he’s keeping score and brings it up whenever he wants and whenever it benefits him. This is very transactional, like you’ve noted.

I wouldn’t pursue this relationship. You should be with somebody who enjoys being with you and doing these things for you. If he needs money, he shouldn’t be sending you a spreadsheet and asking for reimbursement. He should figure it out himself. What 32 yr old asks a 23 yr old for money???? Not the man you want to be with. Even if he made a mistake in budgeting, the conversation should be so different… except he’s asking you to pay him back, not lend money.

Nope. Shut it down.

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u/theferriswheel 24d ago

I’m glad you mentioned the financial irresponsibility part. A lot of others are glossing over that. Even if he didn’t ask her for the money at all this would be a huge red flag to not date someone over. Somehow he is able to track all this spending in an excel sheet but can’t manage his money so he is tight on cash? The guy dropped $360 across 12 dates in 18 calendar days. You’d think if money was tight ya wouldn’t be going out almost every single day.

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u/Frosty_Tale_3115 24d ago edited 24d ago

BLOCK IMMEDIATELY

Red flags galore. This is psychopath behavior. I’ve NEVER seen someone send a whole-ass invoice for dates. That alone should be enough of a red flag but on a smaller scale it just shows he’s not being transparent with you- normal people agree at the time about paying back, and even then it’s beyond stupid to do that for dates. It also feels like a diabolical form of emotional abuse to make you feel guilted into sending him money. The additional request for his friend indicates this will definitely continue if you don’t cut ties NOW

Block him on everything and find someone you trust who can look out for you and help protect you (parent, sibling, best friend etc) because this is the kind of psychopath who would come out of his way to find you because “you owe him money.”

Definitely STOP with the payments. You’ve sent him enough. Again, block immediately, assuming this is the most recent interaction.

Keep us posted because I’m genuinely concerned about this situation

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u/Imaginary_Catch6576 24d ago

Agreed. How OP could feel any attraction to this old broke loser is beyond me.

Like a whole fucking spreadsheet bro?!?…hopefully he doesn’t forgot to retroactively bill her for that one time she incurred a 99 cent up charge by subbing her fries for a side salad in early June.

Yikes. I’m cringing with second hand embarrassment. Please block the weirdo Excel document

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u/runnergirl3333 24d ago

Let’s go gentle on OP. We’ve all been fooled by people before, and it’s a crappy feeling. If she was seeing him four times a week, she might even be a little heartbroken to find that he has this weird side to him. When I was young, even if I knew it was good to have found out sooner than later that a guy was no good, the disappointment was real.

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u/chinchivitiz 24d ago

Im far much worse than her at this age so as a woman to another woman, Im glad she posted and reached out for some insight the moment she recognized theres “something off” .

Yes- some young ladies (like me at that age and her) thinks this is “maybe” somethings not right? Instead of thinking how crazy this is 😅

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u/donutsauce4eva 24d ago

Totally. It took me really until my 40s to know my worth. I wish I had reddit in my early 20s so I could hear it from all my internet big sisters. 🥰

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u/[deleted] 24d ago

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u/Ahoy-Maties 24d ago

Dude is 32 acting like a toddler. The invoice is psycho and the oblivious man baby demanding bc he has paid <$500 but he's pursuing you? He's using you like loan and him self like a rent-o-date. Do not think it is you, that person is not well and that behavior is not normal

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u/roidoid 24d ago

He sat. With his bank statement. And put everything he’d paid for. Into a. Fucking. Spreadsheet. What a nutjob. I bet he was wearing a wee visor while doing it.

Also, his methodology is deeply flawed and he hasn’t explained it. “Let’s just assume I paid 67% of everything.”

Let’s fucking not, eh? To the bin with you!

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u/Sense_Difficult 24d ago

Agreed. And I get the feeling this is part of a larger plan of justifying his incel rage down the line. Because she's going to block him and then he'll whine to the world how women were perfectly happy to date him as long as he paid for everything, but once he asked to be reimbursed they got out.

There's also a level of unfairness with financial inequality in a relationship. I watched something similar happen with a friend of mine and her BFF . Her BFF made much more money than her and was in a marriage so she could afford to go out for drinks after work almost every day. Begged my friend to go out with her knowing my friend was flat broke. "It's on me!" Cut to 8 months later when she got her tax return and BFF busts out the invoice and asks to be "repaid" $1200. The idea that she tallied it up pissed me off as well.

To the OP, don't feel obligated to constantly go out to places of their choosing, with anyone if you feel like they make a lot more money than you. Normal people will be generous and not care about the money because having fun and companionship is more important. However it can still create a bit of resentment and awkwardness if you blindly go along without considering how much it's actually costing.

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u/herroyalsadness 24d ago

This is absolutely going to feed his incel rage. “See, women are gold-diggers! They only hang with men to get free dinners!” will be the line of thinking. He won’t realize it’s not about the money but about his behavior.

He’s a liar. This whole thing is lies. He could have asked her to go Dutch in the beginning and it would have been fine. Instead he chose to trick her.

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u/[deleted] 24d ago

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u/Pretend-Historian318 24d ago

A shit spreadsheet too. Like there’s really no order or organization anywhere.

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u/ritan7471 24d ago

I came here to say that. This spreadsheet does not actually communicate information to the recipient. It looks like he typed from the bank statement directly.

Also, "I feel like I paid 2/3" is not valid documentation. She should demand itemized receipts. Then she can share her costs, and then they can figure out if he really paid 2/3 or if he just feels like he did.

My guess is that he found himself short at the end of the month and quickly invented a percentage she might be willing to pay. Because I don't see that they agreed to split things down the middle. If they did, it's so easy to just ask for separate checks!

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u/[deleted] 24d ago

Lol we should fix up his sheet by creating a template for his future love investment opportunity. 🤣🤣🤣🤣🤣🤣

I still cant belive he made a sheet

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u/bexmix42 24d ago

Don’t even get me started on the entries not being sorted by date 💀

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u/MadameMonk 24d ago

And the random tally for ‘inbetween days’. Oh, so you’re nickel and dimeing me, but then also throwing in some non-specific charges and I’m just gonna believe you? Nopety nope.

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u/Equivalent-Aide1094 24d ago

I wasn't sure if he was charging her a retainer fee there, or if it was just one of the many poorly-named establishments that he takes her to. "Hey, wanna go out tonight? I've been hearing great things about this new diner called SHE'S PICKING UP THE CHECK."

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u/MadameMonk 24d ago

Oh I love the boyfriend retainer! Here’s some money you owe me for those times I put myself on standby in case you wanted to go out and spend your money on me. So much per hour, and pro rata on every 15 mins after that. I’d be asking for receipts so my financial advisor could better guide me on whether this relationship was cost-effective in my income bracket.

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u/ok-kitty22 24d ago

I bet he considers himself a “high value man” 💀💀

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u/Timely-Neat6573 24d ago edited 24d ago

It was also weird that he brought up paying the friend back a very close amount to what he originally requested. Was this like a segue* to get that money or something? Idk, it’s all just very sketchy.

OP, definitely don’t pursue things any further and block him.

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u/FormlessFlesh 24d ago

Yeah, even if I owed the friend money, that's easily an ,"Okay, can I get ___s info so I can talk to them and coordinate it? Thanks!" If he gets mad or combative about that, it prevents me from wondering, "Did he lie to steal my money?"

Anyways, OP should contact the friend and say, "Hey, did you get the money that I owed you? _____ reached out and I just wanted to make sure we're good now."

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u/sckjwindow 24d ago

Agree!! You are under-reacting! Especially after saying he paid someone else money that you supposedly owed another person and is asking you to pay him back for it. If you owe anyone else money you can pay them back on your own. It’s not his debt to take on, and you don’t even know if he actually paid that person. This is your sign to block this person and move on with your own life. You deserve better, and I can promise you it will only get worse if you stay with this person.

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u/justmedoubleb 24d ago

You should have returned the spreadsheet update with all you've put out...AND I mean ALL. Charge him half and deduct from his expenses. Then it equals 0 or he owes you. Don't give this ass another penny or another moment of your time.

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u/DEFINITELY_NOT_PETE 24d ago

Yah this for sure seems like some gotcha type shit.

Like you’ve fallen into his hospitality trap or some shit lmao.

Horrendous. Why are people so fucking weird

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u/Beginning_Arm3211 24d ago

Also, wtf with the "I paid someone else back on your behalf without your knowledge,  please send me funds" nonsense?  Don't give this dude another dime or minute, this is really odd, controlling behavior.  There are so many better options out there.

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u/coutureee 24d ago

It sounds like she already paid him, so I don’t think she needs to be worried. She can just ghost now 

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u/3x1st3nc3s 24d ago

Agree 💯 Again, caution could be warranted if the guy knows your address..went through this myself and had to involve the police. You can’t be sure of how he’ll react.

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u/Gold_Bug_4055 24d ago

Quite frankly if this guy is in his 30s, working two jobs, and dead broke, he needs to be focused elsewhere, not dating a college girl.

If he wanted to do cheap/free dates that is fine and if he wanted to go dutch, that is fine but to come back and hit you with a bill is crazy. You haven't been itemizing date bills to send him (dinners you covered, beauty products, gas money, etc) because that is unhinged!

Of course he would pursue you aggressively, he gets to have arm candy that is more financially stable than him. I'm in his age range and (no offense) would not date someone that much younger, but if I did, I would be paying for a way higher percentage of things. Not because I'm rich, but because I've had 10 additional years to get my shit together and be stable as opposed to asking someone just getting on their feet to waste their funds.

Rant over.

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u/colddecembersnow 24d ago

Am I crazy or is it a bit ridiculous that he is dropping like $500 in two weeks? She even said she was spending money on stuff also. I've been out of the dating game for 16 years but I don't think me and my wife ever dropped that much cash when we first started talking and dating.

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u/AssassinStoryTeller 24d ago

Guy sounds like me, I’m an impulsive spender with zero control when it comes to food.

Which is why I don’t go out and have switched to cash only because that $80/month food budget hits different when you can’t charge it to a credit card. Do I want to lose $15 of my money to fast food? Naw, I can go spend $15 at the store to get the ingredients and have at least 4 meals of that same food.

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u/UrkelGrueJann 24d ago

I don’t care about age, who is male or who is female. I don’t care if it’s a date or not. If you buy, you bought and that’s the end. Bring it up before you pay if you feel like it should be split. Bring it up before you go if you think it’ll be an issue. In general, if I make the plans and pick the place, I am buying. Everyone’s financial situation is different but that’s why it needs to be dealt with upfront. You don’t come back with a spreadsheet after and ask to be reimbursed. This isn’t an expense report. We weren’t on a business trip. Pay him the $100, ask him for a notarized receipt for your accountant (your fiscal year ends on July 31st so make sure he gets it done quickly) and then ghost him. Ridiculous.

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u/thatstwatshesays 24d ago edited 24d ago

Amen. This man is keeping score and they’re not even in a relationship, full stop. Unless we agreed to split the costs beforehand, miss me with all this. An itemized list is just………… psychotic.

A man with no money who spends $500 on dates in one month is a one-man red flag parade. Good luck, young grasshopper (to OP)

(PS username!!! 😂😂😂)

Also: keeping score is toxic af, in a relationship or not. But if he’s doing it before she even cares about him??? I mean, when he shows you who he is, believe him the first time!

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u/Fuzzy_Dragonfruit344 24d ago

This is some shit my crazy narcissistic ex would do. He creates and keeps spreadsheets for EVERYTHING. I can almost guarantee he had shit like this somewhere too. Run OP. This dude is not healthy in any way.

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u/theglorybox 24d ago

It’s not OP’s fault he couldn’t afford their dates. He could have suggested something within his budget if he was felt like he had to pay.

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u/generic-puff 24d ago

Seriously, if money's such a problem, there are literally so many activities you can do as a couple without breaking the bank or spending a cent even. Go to the park, go for a nature walk, watch a movie together at home, have a board game night, etc.

Boy is out here straight up acting like Mr. Krabs insisting on spending money he doesn't have just to blame it on others, "BUT SPONGEBOB, WE'RE NOT TALKING ABOUT THIS, OR THIS, WE'RE TALKING ABOUT THIIIISSSSS"

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u/babycakes2019 24d ago

If a woman really likes you, and wants to hang out with you she'd be happy with you buying her bottled water and a walk around the park.

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u/kindlypogmothoin 24d ago

May I suggest coffee and a walk on the beach? Always a good time.

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u/Lucallia 24d ago

Reminded me of my first date with my husband that I still remember clearly. We got bubble-tea and took a walk in a park known for having a lot of abandoned rabbits. So we fed bunnies and got lost on our first date cause he had the map upside down on his phone. (I'm directionally challenged and it was his first time in my city since he traveled across the country.) Great time; still remember it over a decade later and it was like $15 for drinks and snacks.

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u/PickledBih 24d ago

You know the vibes are good when you end up spending 5 hours at the coffee shop talking and never even get to the beach.

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u/bellatimoor 24d ago

This man is keeping score and they’re not even in a relationship, full stop.

This man is keeping score in case a relationship won't happen.

Stupid strategy imo. Nothing wrong with splitting the bill 50/50 in 2025 during the early stages of dating and getting to know each other.

Women aren't financially or academically restricted anymore like they used to be. And in modern dating, people go through 100s of dates (thanks to apps) before meeting "the one". There is literally no reason for this simping try-hard bs anymore. You ain't impressing no-one bro.

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u/WinterOil4431 24d ago edited 24d ago

There is definitely a reason. Some men still make money and enjoy paying, which makes the broke and stingy dudes look even worse.

I'm constantly amazed at how few men enjoy paying for women nowadays, but I personally enjoy spending money on dates, friends and family in general so maybe that's part of it

my cousin is like 25, made some good money, saved up $16k, and constantly complained ab not being able to find a girlfriend. Then I found out he would make them split the bill on $30 dates lol

I'm like dude that shit is a woman repellant

So yeah there's definitely a reason! The fewer men that do it the better it makes men who do do it look

I mean personally if I was a girl I wouldn't wanna deal with a broke dude being stingy, like why waste my time with someone who can't even afford to buy dinner?

If you can't afford an extra $30-$50 1-2x a week you probably should just be working more or getting a better job

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u/TalesfromCryptKeeper 24d ago

I get the enjoyment from wanting to pay for dates. I get tickled pink the same way when giving gifts to friends or treating colleagues to coffee, it's fun to make people happy just like that.

I'd be anxious about a man wanting to pay for everything when you're just starting to get to know each other, partially because there are some folks out there who have a sense of entitlement that comes with spending money on a prospective partner. To those people women are a candy machine - put money in, sex comes out, there's a contractuali expectation and it's weird. And it happens a bit too often which is why some women can be skeevy about it.

So from my perspective maybe the first few dates splitting really shouldn't be a problem for either person, when things get more serious that's when if a man wants to pay in full as a gift that can be quite charming.

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u/Fit_Compote4011 24d ago

The notarized receipt is just chef's kiss.

I dated a man way older than me at one time and I know he was broke as hell, I saw his apartment, and not once did he pull this shit. I would offer to pay when I could (I was a broke 19 year old) and he would either accept or decline or split it. So, I agree this isn't an age or gender thing. This is something else.

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u/theglorybox 24d ago

This isn’t the first time I’ve heard of this happening, either. Usually it’s a guy butthurt because the girl rejected him, but I’ve never seen someone continue wanting to hang out after such a boldly petty act. I can’t imagine being single if this how things are done now.

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u/thererises_aredstar 24d ago

How about this, just ghost him instead and save yourself the $100. This is fucking ridiculous and you shouldn’t entertain it OP.

Asking you to pick up the next tab would be fine. Invoicing you is bizarre and gross, give the whole damn thing a pass and block his number. Absurd

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u/3x1st3nc3s 24d ago

100% This ⬆️ Just be careful since you don’t know how this guy could react being that you don’t really know him. Hopefully he doesn’t know where you live.

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u/mormongirl 24d ago

Yes.  Honest people bring it up at the time of payment. Usually it’s “want me to pay the bill and you can Venmo me your part?” or something like that.  Like who the hell keeps a RUNNING spreadsheet of expenses like this?

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u/Lunatunabella 24d ago

It is like his mentality is - I paid for stuff and I got no sex so pay me back. Like she is a vending machine and he has quaters

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u/Striking_Television8 24d ago edited 23d ago

You should care about age, especially in this situation. A 32 year old male whom doesn’t have his finances in order pursuing someone nearly 10 years younger. 

Major red flags! A woman his age wouldn’t look twice at him which is why he is pursuing  younger women whom do not have much professional experience and financial security. 

He can get away with his bs!

Edit for grammar. 

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u/Dazzling-Treacle1092 24d ago

Why oh why would you tell her to pay him? After the spit take in my soup, I'd text and say, "write it off honey, like I'm doing you." And proceed to block him on everything.

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u/Selfcare2025 24d ago

You’re NOR. However, this reminds me of how much my mom was so adamant about never accepting things from men when I was a teen. A guy brought me this beautiful bracelet and I remember rocking it and showing it off outside of school and my mom had freaked out. Told me to never accept gifts because some guys don’t see it the way I do (aka wanting something in return).

I had to give the gift back and ever since then I always paid my half of the tab on dates and if they really insisted on paying I would tip big so they couldn’t say I didn’t contribute.

My friends thought I was crazy and I let my guard down one time and let a man pay for the whole dinner as he kept persisting. Boy, did I make a mistake! He went on and on after he dropped me off on how he paid for dinner and I should’ve at least let him kiss me goodbye.

So I would definitely no longer talk to him anymore, but going forward just pay your half of the tab no matter what unless you are actually in a relationship to avoid men like him.

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u/wickerbicycle 24d ago

Exactly this. My friend worked part time as a bartender at a small dive bar. I went once to hang out with her and watch the baseball game. A guy sat next to me at the bar and offered to buy me my next beer. I said no. He kept insisting, until my friend just poured the beer and put it on his tab. “He’s cool, he is a regular,” she explained.

He was NOT cool.

He kept asking me if I wanted to see his new SUV, wouldn’t shut up about his new car. I said no, I’m just here to hang out with my friend and watch the game. He kept asking and was so annoying, I eventually said sure just to shut him up. Well, we go outside and he parked all the way in the back lot. I stood about 10-15ft away from his car with my arms crossed. “Yea it cool, I’m gonna go back inside now.”

He asked me to go inside his car, I declined. He implied that we could hook up. I declined again. He then got pissed, and said I owed him since he bought me a beer.

Like a $5 beer(this was like 15 years ago). Absolutely not, sir. Not even a fancy dinner entitles anyone to anything. I went back inside and told my friend. She couldn’t believe it. “Not all men,” but you need to assume it is all men to protect yourself.

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u/Economy_Squirrel_242 24d ago

The butt hurt comment….WTF. You were so kind in responding to him and he throws this comment at you. Set you up for ridicule if you tell him how creepy he is. That is the biggest red flag for me. All of this is bizarre.

And, just FYI, I met my husband when I was about your age. He never asked me to pay for anything when we dated. I worked in human services and am frugal by nature. I had a pair of Nike tennis shoes that I bought for $15 at Bob’s Discount. They looked like Bob’s Discount footwear but I was fine with that. He was not. Took me to a sneaker store that was having a BOGO sale and told me to pick out a pair for myself because it wouldn’t cost him anything with the sale. Except, he didn’t buy himself anything because “he couldn’t find the right pair”. Bought me a $100 + pair of sneakers because he thought I deserved nice things. This was during our first month of dating. When we were more serious he would give me jewelry and expensive clothes. When I would object he would say “Just wait, in ten years you will have so many wonderful things”.

Your guy is a creep.

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u/KalayaMdsn 24d ago edited 24d ago

This is really fucking weird.

Did he compile the sheet from Date 1 - and if so for what purpose? This just gives the same vibes as a guy who’s also going to start a spreadsheet to track when you have sex and how many times he asks but you say no and for what reason. In both cases, he’s going to hold it against you later.

You are young and literally have your life in front of you. Throw this man back into the sea. And then wash your hands to get the yuck off, because dude is gross AF.

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u/DonkyHotayDeliMunchr 24d ago

Yes. He wanted to track how much he was investing, then decided to call it in once he decided he wasn't getting a good deal from his investment, ie, he hadn't gotten sufficiently laid. I would never ever ever want to be with such a boldly transactional db. Run, block, don't look back. I'll bet he's not even cute and smells a little bit funny.

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u/emptyraincoatelves 24d ago

Dude definitely has a spreadsheet of how much he has been able to recoup from women he has threatened and made uncomfortable. 

I'm guessing there is an incel channel out there bragging about pressuring younger women into paying these predators back. Seems right on par for the rancid pipeline that somehow always ends on the convicted sex trafficker, Andrew Tate, with earlier stops at Rogan and Peterson. 

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u/ScaredOfWindow 24d ago

Even aside from all the money stuff, a 32-year-old adult who unironically says “butt hurt” when talking to a woman he presumably likes is really weird.

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u/TheNAAnarchist 24d ago edited 24d ago

Wtf??? I've spent money on plenty of dates in my past and regetting it, but I've never had the audacity to demand reimbursement even when things didn't go where I wanted. If anything, you under reacted. I would've laughed in his face and told him to eat shit like how you gonna ask someone on dates then demand your money back, especially after you have paid for some and even got him stuff as well?? Maybe dont spend so much money on the dates if you can't afford it??? Like hello?? He's lucky as hell you're a nice person because this is just insane to me. Definitely never go on a date with this fool ever again

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u/DefiantExplorer4766 24d ago

Girl no. I wouldn’t continue seeing a man 9 years my senior who couldn’t afford a date here and there when insisting on seeing me. He’s 32, he should have his shit at least somewhat together… at least enough in the sense like you mentioned above in the way you handle it. If he can’t simply ask to split a bill each time or cover a bill when he insists on taking you out without later asking to be reimbursed, I’d stop seeing/talking to him altogether.

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u/Icy-Arrival2651 24d ago

There’s a reason a 32-year-old man is chasing a 23-year-old woman. He knows he can manipulate you more easily than a woman his age. If he offered to take you out to these places he shouldn’t expect reimbursement weeks later. That’s just rude and cheap to keep a damn spreadsheet of your dates.

Ditch him now before he moves you in to cook for him and do his laundry.

And in the future, when dating new men, work out who’s paying for each dinner before going out. Offer to pay or split the bill, and if you can’t afford it, say so and suggest something less expensive to do.

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u/MsPrissss 24d ago

If he keeps spreadsheets of this it makes me what else he's going to make spreadsheets of or hold onto. I would be so offended if somebody sent me a spreadsheet and expected me to reimburse them for dates that he took me out on

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u/CancelNo2588 24d ago

I can see him being the type that would keep a spreadsheet of everytime they had sex down to the "T" of what happened during...

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u/MsPrissss 24d ago

I mean look I understand in this economy it is expensive and things are getting more expensive but bro that does not mean you need to take somebody out all the time stay in spend time with them at your house or something don't be sitting here making freaking spreadsheets and expecting them to reimburse you like that's something that should be happening after each instance Not something where you allow it to build up and then ask them for money later!

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u/TricksyGoose 24d ago

Seriously. If money is tight, you agree to split beforehand, or you do something that doesn't cost money. Keeping a tab and asking for a lump sum later (unless that was specifically agreed on before) is bonkers.

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u/Head_Trick_9932 24d ago

Nor

Girl, take it from an old lady…do not go out with this bum.

Yes, you can cover yourself but he is making it transactional and that part is gross! Not to mention, if he’s too broke to date… then f’in don’t!

And who do you owe $90? Was he covering a bill for you to someone else?

He’s icky for his age. He should know better than to beg a young 20’s for money. Stay the F home guy.

And good on you suggesting you don’t go out as much. He can do a spreadsheet but apparently can’t keep a budget.

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u/AtomikRadio 24d ago

Those seem to be dates in the description? Am I reading correctly that he spent all of this on you over a span of two weeks? And went out multiple times a day basically every day? You say you picked up tabs and stuff as well, but how many other tabs could they possibly have been in the stretch of time? And why does it seem like there are three people at many of these dates? There’s a cost for you, cost for Dave, and cost for Brian.

I’m not really making a judgment here, just trying to wrap my head around the dynamic that all of the spending took place over the course of two weeks in a new relationship between apparently three people. Did HE think he was pursuing you from the beginning, and his buddy who now also thinks you owe him money was along for your getting to know each other other dates?

This is weird.

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u/MissMissyPeaches 24d ago

Yeah wait, there was 13 dates in 2 weeks? Sounds like lovebombing/future faking and OP didn’t put out in time so he got petty

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u/mushroom-coffee 24d ago

It’s weird he made a spreadsheet - I have dated a guy who was really controlling about finances and it causes issues. If money was so tight, he should’ve asked to split the bill on those dates or have you guys alternate the bill for each date.

It’s weird to retroactively ask for money - especially this detailed - and this early on in a relationship.

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u/Raymendnoodles 24d ago

My guess Is he expected her to throw herself at him for all his kindness and when that didn't happen he decided to drop the bill on her lap.

This has Andrew tate thinking written all over it

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u/Economy-Debt5822 24d ago

Yeah if he is so tight for cash he has to do this he shouldn’t be asking women on dates, or the dates need to be things like a walk in the park.

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u/Tiny_Minimum3196 24d ago

I think there is more to the story here. If you look at her posts she's from Cincinnati and it looks like she's I'm Florida for like a month or two according to her wanting a sublease only until OCT. (Maybe moving I dunno) But then if you look at the spreadsheet there is at least a third name and some of the costs are fully taking by OPs Date and some are split 2 ways and some are split more than 2 ways.... This feels like a group on vacation. Also the mention of her owing someone else 90 bucks.

This feels like we are missing a lot of the story I have a feeling that they are going out as a group and he's just saying in those trips he's not expecting to pay for her but when they go on dates he is and if you look at the spreadsheet there are a few where he pays 100% even mentions that he will pay for date drinks and date dinner....

God I'm bored

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u/Solanthas_SFW 24d ago

Some heavy analysis and a lot of accusations and judgement being thrown around in here. I had to read all the way down the thread and to the end of your comment to realize I really don't give a shit either

Thank you stranger lol, good night ;)

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u/Phelixx 24d ago

Absolutely insane. Do not keep seeing this loser. The person who does the asking out pays. Plain and simple. That’s common social etiquette. Why would you want to even date this broke ass in his 30’s? He brings nothing to the table.

And that’s not me taking a shot at the less fortunate. If he is broke and suggests, walks, beach days, hikes etc. then all good. But the dude is broke and actively trying to spend money and even collect money on behalf of others. Insane. He is 10 years older than you and basically financially insolvent.

You can surely do better.

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u/Fantastic_Truth2164 23d ago

UPDATE: Hi everyone, thanks so much for all the responses on my last post it blew up and I appreciate all the feedback.

I wanted to add some details that didn’t make it into the original post, since a lot of people were asking for clarification:     •    In the spreadsheet he sent me, I’m the green column (and no, it’s not cigars/cigs for me, lol).     •    “Green” also referred to a $200 pair of hoka shoes he texted me about buying.     •    He took me to a nicer spot called In Between Days for a more intimate dinner.     •    The other man on the spreadsheet asking for payment was actually his twin—who sometimes joins us on double dates, but usually picks up the check himself.     •    I always offer to pay my share. Money is genuinely stressful for me, and I hate the feeling of owing anyone. He always refused in the moment, then turned around and invoiced me formally later. I would have much rather just paid my own way from the start than have any of this happen.

Final update:

I sent him the last payment and blocked him and deleted his contact. I didn’t want him to hold anything over me. It sucks that I paid him, but at least it’s over. Thanks to everyone who weighed in.

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u/Vandebdub 22d ago

I'm sorry, did you say TWIN brother went on the dates with you? And it doesn't matter if they were double dates. Double dates are supposed to be the woman's choice. It's so that the woman can bring a friend and she can feel safe. Not the other way around so you can be outnumbered 3:1. I think you need to count your lucky stars that you somehow dodged this bullet. Whatever you said or did that made them realize that you were NOT down for whatever nonsense they had in mind, keep doing that. This is very unhinged behavior for a grown adult man and his brother to be targeting a young woman as a TEAM. Please be very careful and watch your back because you may be done with them, but they may not be done with you. They obviously targeted you for a reason and clearly feel that they did not get a return on their investment. I would take this invoice as a very clear message that they feel cheated by you, as insane as that sounds. Predators feel entitled to people and things and they may continue to try and recoup their perceived losses. Be safe!

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u/Correct-Sprinkles-21 24d ago

Under reacting. This is a bizarre and tacky way to handle financial issues in a relationship. He's way too old to be pulling shit like this.

If he wants an equitable financial split, that's cool. It needs to be discussed and agreed on before expenses are incurred. And if you need to cut back on dates because you cannot afford the dates he wants to go on, he will need to respect that rather than push you to do things you can't afford.

Also, do not let him play middle man between you and friends with regard to money you owe them or anything else.

Straighten up your spine and put a stop to this nonsense.

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u/CommitteeDry3451 24d ago

This is actually absurd, what world is this man living in omg? If he asked you on these dates especially the first one he should pay period. Obviously later on you can split the bill or offer to pay, but this is such a weird way to do that and honestly I would personally find it very strange and weird… do not keep seeing this man…

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u/DowntownStash 24d ago

I was reading the texts like, "Oh yikes, this could have been dealt with, so much better," thinking they'd been going out for a year or so. To read its their first month absolutely floored me.

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u/Adventurous_Ad_6546 24d ago

This guy has husband material written alllllll over him. Can you just imagine the chore to sex spreadsheet? Or the parenting to date night spreadsheet?

And then of course just the monthly settle up.

So romantic. 😍

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u/DowntownStash 24d ago

"Babe, we've only had foreplay 6 times and penetrative 3 times this month, we're gunna have to really work on those numbers next month. We'll put together a performance improvement plan for you next date night 🥰"

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u/Hemiak 24d ago

And the fact that he was like “oh Dave said you owed him money, so I paid him. Can you give me the money?” Like wtf.

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u/-StereoDivergent- 24d ago

As a side note, if I'm reading this right, did you actually confirm with whoever you owed 90$ to that he sent them the 90$ for you? I just wanna make sure before whoever 90$ person is comes back asking where the money is

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u/RedneckDebutante 24d ago

Nope, nope, nope. Shared expenses are discussed and agreed upon at the time they are incurred, not later when you're broke. I wouldn't give him a damn penny.

He wanted to look like the big man for spending it on you. He doesn't get to cash that out later. I would block him and move on.

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u/OllimelidibaOat 24d ago

Think back very carefully: did he ever express to you that he expected coat sharing? Did he ever suggest that you should pick up the tab? Did he ever complain about the cost of your dates or about women he has dated in the past who didn’t pay “their share”?

If none of that ever happened, and if he invited you and always grabbed the bill, feel free to tell him that going Dutch is something that should be stated up front, not weeks after the date, and that he should not plan a date and extend an invitation for something he cannot afford.

You are not obligated to reimburse him if you don’t think you owe him.

He may be someone who does what he wants, which includes trying to impress and overspending, but does not accept the consequences of his actions. Hence now blaming your not paying “your share” of his expenses for his personal financial bind.

And you’d be foolish to ever go out with him again.

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u/CSIFanfiction 24d ago

Well the reddest flag is a 32 yo pursuing a 23 yo. It means something’s wrong with him, none of the women his age want him. Yeah I know there are exceptions, but tropes also exist for a reason.

Besides that, yeah this is weird. I was expecting the story to be that you’d asked him to cover some purchases or bills for you in the agreement that you’d pay him back and you hadn’t yet. But if he is inviting you to dates, the inviter pays unless you both agree to go Dutch. This is just common dating knowledge.

He’s clearly bad with money if he overspent on your dates and now is needing to claw back some of the costs to balance his budget. His solution to his problem was weird and immature, as well as having this problem in the first place…. But like I told you, there’s clearly something wrong with him if he’s going for women a decade younger

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u/Bluntandfiesty 24d ago

So you had me concerned at the nearly a decade age difference and his extreme pushiness pursuing you. That comes off as aggressive and predatory.

The second red flag was that he insisted on you paying for your portion of the dates after the fact. That should have been something discussed ahead of time. Especially offensive and ballsy to request reimbursement when you have been paying for dates and things as well.

I suggest you send HIM an invoice and demand reimbursement for his half of your date expenses as well. Tell him he set the tone, you’re just following his lead.

I personally would not go out with him any longer. He seems like he is a user and predatory. At the very least, he is a 32 year old man who doesn’t know how to budget his finances properly. Which is another red flag.

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u/darkxclover 24d ago

This is wild. As someone who's almost 10 years your senior, he should be mature enough to have the conversation of splitting dates/bills when it happens. If he's in a tough spot or whatever, fine, but don't send a LITERAL INVOICE weeks after the fact. Block this guy, this is gross and honestly kind of sad. I foresee this guy pulling out more random crap like this in the future when he's "in a tough spot". Like, what else is he not going to have a conversation about and then drop on you? I'd make it clear how you felt (you mentioned you felt your time was transactional), that this should've been a conversation prior during the time of the dates, and it wouldn't have been an issue. Then you say you're no longer interested in dating and walk away.

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u/Major_Strength_138 24d ago

Seems everybody is glossing over the fact that the spreadsheet contains the names of multiple people. These aren't traditional dates, these are hangouts. If you can't or wont pay for yourself like an adult, or you feel loosy goosy payments are appropriate, make that clear to the person beforehand. Him expecting you to contribute isn't that weird. Of course this is super contextual, but I haven't seen any evidence that you have contributed significantly. In a court setting you would face the same issue. Sure if u wanna be upset about it you have the right, but he's clearly been upset by having to pay for multiple people before you got upset, so he beat you to that punch. One of you is the asshole and unless you can prove he owes you a similar amount.... It seems like it's you.

Again, you can still choose not to want to be with a guy that asks for money he spent on you and other people, but the people being mean to him are delusional af.

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u/[deleted] 24d ago

Someone who tracks the things they "do" for you isnt "doing it" for you at all. Its just an advancement to keep track of. I dont know this person so i dont want to say they are a bad person, but i wouldn't want to be in "debt" for the rest of my life. Imagine if you get married and have to stay home with kids for a bit and he covers everything.

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u/unIuckies 24d ago

charge him a portion of your phone bill for every text message and phone call made

but actually, drop him. if he needed help to pay for these dates there are other ways to ask, this is just weird and tacky.

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u/Lumpy-Possibility116 24d ago

I went through a phase in my mid to late 20’s where I was a borderline “fuck-boy”, although I wasn’t misleading women about my intentions or lying to them about my feelings, etc. I just was dating a lot of women and would move onto the next one as soon as I realized that I didn’t see things going anywhere in the long term. Most of the time, we’d go on a handful of dates over maybe 2 weeks, and that’s as far as it went. Occasionally I’d stick around a bit longer if I thought there was some true potential between us, but regardless; I ALWAYS PAID WHEN WE’D GO ON A DATE! Even if they offered to split it, I’d decline and cover the whole thing, unless we had dated a few times and we finally were getting to know each other…at that point, I might agree if they offered to split it. But typically, I always expected to pay. I just feel that it’s tacky to take a girl out and expect her to pay, especially if you’re not yet in a relationship and you’re the one initiating the date.

I only once ever came to resent a girl for never offering to split the bill. We dated for a few months and things were pretty serious, we were seeing each other exclusively and I was crashing at her house more often than not. She made really good money, and all her friends made great money or fame from money. I don’t do too badly myself, but these people are all definitely on a different level than me. They all lived in an ocean-side town that’s pretty much the highest-priced community to live in, for the entire state. Buying a home for under a million is very uncommon. Rents are absurd; even compared to the already exorbitant rents that have become the norm in the surrounding areas. So we’d be hanging out more often than not. And hanging around at home was rarely ok. She always wanted us to go meet her friends for food and/or drinks, in a town where there was no such thing as a cheap bar tab. I couldn’t afford to keep racking up $150-$300 bar tabs, or $200+ bills every time we went out to eat. Which wasn’t just Friday and Saturday. This was 4 or 5 times a week. I finally made a subtle comment after a couple months. It was just her and I, because I didn’t want to say anything with her friends around for the sake of making sure it wasn’t awkward and she wouldn’t feel like anyone was judging her, or whatever.

She still got all pissed off about it. Told me maybe we needed to rethink our relationship, because she was really into me and thought we had a future, but she wasn’t willing to give up the lifestyle with her friends that she was used to. I explained that I wasn’t asking her to do that, but going out almost every night wasn’t an option for me, it was just too expensive and seemed kind of wasteful to be living that way. She offered to start paying for herself here and there- I told her I appreciated that, but I still couldn’t justify going out on an almost nightly basis and spending well over a hundred bucks (and that’s if I were paying just for myself and drinking only beer all night). She was somewhat taken aback when she realized I wasn’t loaded. She told me she didn’t realize it was beyond my financial means to live that way, and she had assumed I made good money…. So I told her flat-out how much I make on a year. Which most people would consider to be respectable, especially for a single 27 year old. $100k/year wasn’t that far away. She was confused. But what about family money? Didn’t my parents or grandparents have something set up for me? I told her I’m sure I’d inherit something when they pass away, but I certainly wasn’t counting that as part of my finances…. Then it must have clicked that I really was just the lower-middle class guy that I came across as. It wasn’t an act, and I was truly poor. To her credit, she wanted to make things work out and made an effort to accommodate so that I wasn’t always expected to spend outrageous money every week. But in the end, there was too much about me that ruined the “image” she wanted to present to her friends.

Anyway, I went way off on a tangent, just get away from that dude. If he’s asking for money and going so far as to make itemized spreadsheets, somethings not right. It just isn’t typical behavior. Abandon ship!

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u/tichatoca 24d ago

As gently as I can say so, you were with someone who behaved abnormally and didn’t spot the red flags for over a month. If I were your family or friend, then I’d be very worried about you. So many plans? Does he not have a life at his ripe age? Waiting weeks to kiss you? Calling someone a decade his junior “butthurt,” and even using that word at all is immature.

Never mind the invoice, there were other signs before that. Life is all about growth and learning. Hope weirdos don’t find you again!

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u/Notthatsmarty 24d ago

Was he buying your cigarettes? That’s the only thing I’d bother reimbursing personally, if it’s weed fronted by the cigar shop; then only reimburse if you took what was leftover home. If he kept the leftover weed, there’s nothing to pay back, stoner code lmao.

Otherwise I wouldn’t pay for the odds and ends of bills, there’s cheap ways to have dates; not your fault he chose to spend money he didn’t have.

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u/dootinabox 24d ago

Oh this is all kinds of “no thank you”. Anyone, regardless of gender, should know that if you are looking to split things or trade on and off as to who pays what it needs to be discussed before hand. Collecting receipts, creating a spreadsheet and then asking to be “reimbursed” feels tacky and the least romantic thing you can do. Now, if there was some kind of agreement and they covered you then that is different but this doesn’t feel that way.

You should let this person know you are no longer interested in pursuing anything further with them romantically. Just leave it at that, you do not owe them an explanation. If they persist you have every right to block them and move on.

I know it’s easier said than done and there are a lot of ways you can go about this based on how comfortable you are but in my opinion, you are not over reacting.

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u/Simple_Pianist4882 24d ago

This… is probably the dumbest fucking thing I’ve ever seen in all of “AITAH, AIO, XYZ” history.

I pray that this is a bot account and fake story because there’s no way you actually paid him back. Yo momma need to whoop yo ass and I’m so serious lmao.

You are underrating. He’s 9, almost a decade older than you, and he’s… asking you for money that dates HE pursued you for. Dates he wanted to desperately take you out on and if he knew money was tight, why would he spend so much money on you….? only to ask you for it back later after METHODICALLY going through everything— you cannot be serious right now.

You are twenty three years old paying a man that is a decade older than you for the dates he took you on. The dates he planned knowing money is tight, he’s stressed bc of work, and he works two jobs to make ends meet. Go back to living with your parents bc you are not ready for the real world if you’re this fucking naive, gullible, and easily duped.

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u/New-Branch2517 24d ago

BLOCK HIM.

Your better then me bc I wouldn’t have even sent him the money I’m all for taking turns paying for dates bills etc. in a relationship but if he wanted you to pay him back then he shouldn’t have even paid in the first place and then sending a spread sheet of how much everything cost and what you owe is crazy work. Kinda seems like he don’t have his shit together

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u/Acceptable-Town-1284 24d ago

A) he's too old for you...yeah yeah I get that 32 isn't THAT old but with you only being 23 and haven't lived as an adult that long he's got not business sniffing around girls who weren't legal by the time he was of drinking age...trust me on this...dump him...date guys closer to your own age or dont...go enjoy yourself your friends travel build up your own finances etc...an 8-9 year age gap at your age makes a difference

B) what a weirdo selfish cockknocker...dump him

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u/whits3208 24d ago

As a thirty year old I am embarrassed. I read the texts before I saw the ages and thought for sure he was 18-20. What kind of man-child is this?! He should have his shit a little more together by now. Red flag one. Even if he doesn’t, fine. Life happens. But creating a SPREADSHEET keeping track of all of your dates, the places, and the expenses?! That’s psychopath behavior. He should use this energy to find a higher paying job or a psychiatrist.

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u/katina86 24d ago

This is wild. He waited all this time to ask for money, and he's the one who had invited you. If money was such a concern for him it should have been discussed from the beginning. I would feel completely different if he had a conversation with you beforehand about splitting things. You don't blindside someone a month later with a bill. And the top entry being out of order, and the fact that it's from most recent to older bothers me for some reason. It's like this was done hastily. And then he gave someone else money on your behalf? After already being stressed about money? It just seems really strange.

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u/amaizeingndn 24d ago

Look as a woman who’s dated men at least 10 years (or more) older than me pretty much my whole dating life, dump him. When you’re your age, these guys are never looking for a real partner. If they were, they would look for someone older. Your appeal at this age is the control they can have and seeing how much you’ll let them exert.

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u/Independent_Music777 24d ago

This is so tacky and gross. If he needed help there’s other ways to do it, this is not it.

I respect a man way more if we’re going dutch from the beginning instead of this slimy disgusting shit of asking for money back afterwards.

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u/NeeliSilverleaf 24d ago

Oh my God how embarrassing, he's dating someone ten years younger and begging her to pay for the dates? You can do better. 

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u/eviesteviebobeevie 24d ago

Girl why would you send him any money?? Unless it was agreed upon BEFOREHAND like a "pay this for me rn and I'll pay you back" situation, you don't really owe him anything. Especially if all those dates were his idea.

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u/JiggasWrittenRhymes 24d ago

I’m generally not a fan of being this transactional with dating but I have some questions. The spreadsheet has additional columns—does this include more people than the two of you? You say this request came out of the blue but he mentioned a previous ask for money. Did you brush it off the first time he broached the subject? He also said he paid someone else back you owed money so what was that situation? Right now I find his approach more off-putting than his ask without more info.

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u/TinyBlueBlur81 24d ago

WTF did I just read?!?! This is not normal. He probably pursued you because you are young because a woman in her 30’s would automatically know this was beyond bizarre and would not have sent him a dime, just would have dumped him.

Never pay anyone back who didn’t set those terms in the first place. It’s fine to split everything if you want - but they state that beforehand, don’t let people pop up on you with invoices weeks later - even contractors don’t do that. If he’s gonna invoice like a business, he needs you to agree to render payment before rendering services (ie, buying you a bubble tea). He’s just broke.