LTR of 8 months, excellent all around except this one issue: money.

She has a lot of college debt, does not make a lot at her job, and basically never has money on her due to her bills (student loans, apartment rent, car, utilities, etc.)

When we first started dating, we’d often just split the bill. However it quickly started to turn into her always asking me if I could put the full bill on my tab, and she would Venmo me later. I was fine with this in the beginning.

Except I quickly learned that she is very bad at ever remembering to pay me back. Weeks will go by and I would be forced into the awkward position of saying “hey could you Venmo me that $40 this week?” I’m understanding of her money troubles and I don’t pressure her to pay me back quickly. But I suspect she wants to wait and wait until I forget about it or until it gets to the point where she can say “really? You really want the $40 from 6 months ago?”

I suggested that we just pay for our own stuff. I pay for my meal, she pays for hers, separate checks. She has a BIG problem with this. Saying she doesn’t like that, and you treat each other when you’re in a relationship, “that’s just what you do”. Treat each other meaning I pay this time, she pays next time. Except, how would she pay the full bill when she never has money on her? I can also see the writing on the wall that I’d end up paying for the expensive meals, and she’d pay for the cheap stuff.

She is now shaming me for not helping her out more. It seems like she won’t be happy and this problem won’t go away until I end up paying for everything. In my opinion, not only do I help her out in ways that are being ignored, but me shouldering the load is a one way street to betabux city. (Many of her friends BF’s are big time betabux, and I know this affects her too).

Have any of you guys dealt with this, and how did you handle it?