I (f, 19) have been with my boyfriend (m, 21) for about 4 months now (kind of on and off again). We recently got back together and I’m having the same issues I’ve had since before we started dating. I would like to preface that I am NOT a gold digger. My parents died a few years ago and I’m funding myself through college by working 3 jobs. Yes, money is tight, but I have always managed to figure things out and still afford to have a good time here and there. My boyfriend, however, is pretty well off. He has a trust fund, and a pretty secure checking and savings account, with his dad paying for most school related expenses. Despite him being financially secure, I have never asked him for money. It goes against a lot of my personal values, and I would never feel comfortable knowing he gave me any substantial amount of money. The problem comes in with our dates, though…there are none. Since we started going out, he hasn’t paid for a single date. And when I suggest dates that cost money, he refuses. I even offer to pay for myself, and sometimes for HIM, and he still says no. We’ve only been to free locations or his apartment. Even when we’re on dates, he’s so reserved about eating, to the point where we can spend days together and only eat one actual meal (and it’s always McDonalds, yes I pay for myself). I’ve told him that I don’t mind covering myself, and yes, money is tight for me, but it’s never stopped me from having a good splurge here and there, but he doesn’t care. And he NEVER offers to pay. Maybe once in a while he’ll cover something, but it’s never been anything more than $15 at a time. No flowers, no gifts, not even a heartfelt letter (and I made him a huge gift basket for Christmas, filled with both homemade items and a more pricey gift that I made sure to save up for). I tried to talk to him about it, ask him if we could do more stuff out, and he said that if I loved him enough, I would just be content hanging out with him, no matter where it is. It’s not just that he’s preventing me from taking advantage of him (which i would NEVER do), but he outright stops me from doing anything fun. I’m honestly starting to see why he also deals with his own mental health issues, because he never goes out and does anything. My friends think I should just dump him for good and not look back, but I really do love the guy. When he wants to be, he’s romantic. I just feel so bored when we’re together. AITAH??