With friends, it's easy not to be transactional because people usually pay for themselves. If they want to share (e.g., liquor, food, etc), that's their own prerogative. There's no sense of indebtedness around friends, which I would say is relatively normal. Yet, it doesn't apply to me and romantic relationships.

I used to be BB as hell, and paid for my girlfriend every time we went out. That was when I was 22 and employed; she was unemployed. I found it increasingly difficult to have to work, and pay for her consistently, because the sex was highly unsatisfying and infrequent. I broke up with her, because I got really tired of it. My parents are traditional, and in our culture, guys are expected to pay for girls. But I was raised in America, and feminism has now gotten to me.

Equality. If two people have equal earning potential, then I think they should split the bill. Having the guy pay, just because of cultural norms, seems so outdated since I was educated to believe in the concept of equality of genders. It seems like the guy is paying for the girls attention. So, since breaking up with that ex mentioned above, I've been trying to date girls who can pay for themselves. If BOTH people are paying their share of the activity/food, then it's easy to believe that they BOTH enjoy each other's company.

I'm 24 now, and I'm thinking about pursuing a PhD. Which means that I won't have very high earning potential - definitely while I'm still studying, and until I get a practice running. It means my savings from working years ago will be scarce. I'll have to be cheap as shit. Which would, I think, only amplify my transactional lens. I will be less inclined to pay for girls, because I know I need it for myself.

I enjoy being in longer term relationships. I like that intimacy. I just can't reconcile that with my transactional view of the world. I try to excise everything that isn't bringing me value. It takes me a while to enjoy women. It's rare for me to have feelings for girls. But when I do, I can't help but feel like I'm paying for her attention everytime we go out. Like I'm unworthy. Finding girls who already make money is theoretically fine solution. But, why would they even bother with someone who doesn't earn even more than they do? Hypergamy and all. It seems so fucked.

How do I:

a) relearn to enjoy paying for girls b) stop viewing human interactions transactionally c) explain why I am less transactional (and thus more generous) with my friends, but not with women?

I apologize if I'm not too coherent. I'm trying to make this problem a bit more general rather than situation-specific.