Woman breaks up with boyfriend after he asks her to 'pay him back' for her 'share' of dates. AITA?

"AITA for breaking up with my boyfriend after he asked me to pay him back for my 'share' of our dates?"

I (26F) have been dating this guy (29M) for about two months. He’s incredibly sweet, thoughtful, and we get along really well. We’ve been going on a lot of dates—dinners, movies, a few weekend trips—and I was really starting to see potential in him.

From the beginning, he always insisted on paying, and whenever I’d offer, he’d just smile and say, “We’ll handle it later, don’t worry about it.” I didn’t think much of it. On the rare occasions when I did pay, he’d always ask me how much I spent, which I found a little odd, but I just assumed he was particular about finances or something.

Then, out of nowhere, he texts me saying he’s a little tight on money and asks if I could send him some of what I “owe” him. I was confused because, as far as I knew, there was nothing I owed him. When I asked what he meant, he told me to download an app called Craify, where I’d be able to see all the expenses he’s tracked.

So, I download the app, and the moment I log in, I see every single dinner, coffee, Uber, and even a gas station stop listed under my name—with a total of $520 that I apparently “owe” him.

I was completely caught off guard. He never once mentioned that he was keeping track of everything. I thought he was treating me on these dates, and if he wanted to split costs, he should’ve said something before accumulating a tab. It felt less like a relationship and more like I’d unknowingly opened a line of credit with him.

I told him I wasn’t comfortable with this and that I wished he had communicated it upfront. He said he just assumed this was fair and that, since he grew up poor, he was always mindful of money. He wasn’t rude about it, just very matter-of-fact. But to me, it just changed the whole dynamic of our relationship.

I ended things with him and did not pay the $520. But now I feel a little guilty. Maybe I overreacted? Maybe this is just how he manages finances because of his background, and I should have been more understanding? So, AITA?

Here's what top commenters had to say about this one:

Wizard_of_Claus said:

NTA at all. What a strange thing to do. My guess is that he wanted to look like a big wheel and then realized he couldn't afford it and wanted a refund lol.

Thin-Policy8127 said:

To me this reads as manipulative because you were willing to pay your part up front. This is the same thing as someone giving you a gift and then holding it over your head for the rest of your relationship "Well I got you X six years ago so..." No, that's dumb.

Also, you dodged a bullet. I've known people who do their finances this way and while it's "smart" in the paper-sense, it's brutal emotionally over time. He should have communicated to you up front that this was his expectation. You can't be responsible for "your part" in a game you didn't know you were playing.

Antzcookie said:

NTA. It’s one thing to offer to pay or split costs, but it’s another to secretly build up a “bill” and then spring it on you like you’re on the hook for a loan. Relationships should be about mutual understanding, not surprise invoices.

If he wanted to split costs, he should’ve said that upfront, not made you feel like you owed him a chunk of change after the fact. You dodged a bullet.

Pinwurm said:

NTA. If he had told you on the first date that you were "opening a line of credit" with him, any reasonable person would’ve either split the bill then and there or agreed in advance on a Venmo request within a day or two.

Instead, he insisted on paying in the moment and said nothing about splitting the costs. That makes those meals a gift. It’s unethical, childish, cheap, and just plain stupid to ask someone to pay for their own gift, long after the fact.

Be happy it was only two months. If anything, you’re underreacting. He invoiced you rather than accept expenses as part of the cost of dating. He’s a terrible communicator who “keeps score” in relationships. That's what this is. This behavior would’ve shown up in other areas of your lives, guaranteed. You dodged a bullet.

erica5577 said:

NTA, you offered to split the bill he said no so you don't owe him jack. And the fact that he kept track of everything is creepy and manipulative.

HickAzn said:

Dodged artillery, not just a bullet. What a whack job. NTA.

PopularSchool8975 said:

NTA. You thought you were dating a man, not Master Card.