Gents, this thread has been awfully quiet the past while, I'm sure due in no small part to my absence. While I am not making a triumphant return to singledom, I am looking for a bit of advice with the lady friend. Everything's pretty awesome with this girl overall. She's hot, smart, completely sane, and seems to think I'm pretty great as well. She even seems to genuinely laugh at my awful jokes, and actually gets that I'm being sarcastic most of the time (a lot of girls don't know how to take me and get offended). I can honestly say that in the 7 months we've been dating we have not had a single fight, and barely even had a disagreement. No passive aggressive, "everything's fine" when it's not fine bullshit. It's really quite refreshing to be in a relationship that honestly requires almost no effort on either of our parts to make work.
What I'm looking for advice on is on financial issues. I do okay for myself and don't really sweat the small stuff in terms of going out to eat, buying clothes or recreational equipment, and so on. She on the other hand is between careers at the moment, with a BA in psychology, intending on going back to get a master's of some sort in a year. When I first met her she was waitressing full time and doing a bit of research work at the University. Both of us were getting a bit sick of not seeing each other much, so after she got word that she didn't get in to the master's program she'd wanted to she started applying for jobs in her field, but with only a BA it's been tough for her to get much. Right now she's taking on shifts as an aide for kids with autism. As far as I understand it, she goes to people's houses and works on various skills and exercises with the kids. But she's only doing that 10-15 hours a week, it hardly pays ($15-17 an hour I think?), and it prevents her from working at her restaurant most week nights. So she's only working 15-20 hours a week at restaurant, mostly Fri-Sun. On top of that we're trying to get out on the weekends to do a lot of camping and hiking etc in preparation for hiking the West Coast Trail in August (that will be the true test of the relationship!). She probably makes the majority of her money Fri-Sun, so that's hurting her too.
So while I've never really discussed money with her, I'm pretty sure she's near flat broke. She's got student loans, not sure if she has CC debt. Owns a beat up car, but it seems reliable and decent on gas. Her parents have done okay, but are small town middle class types, so I'm not sure if she gets any help from them. When we go out for eats or whatever I pay as often as she'll let me. Initially she insisted on paying probably near half the time. More recently she's being less insistent on paying, which is fine by me, because she can't afford to. I've told her so long as she picks up some groceries and cooks a good meal once or twice a week, I consider us even if we go out for dinner or brunch a couple times a week, and she seems happy with that because she likes cooking.
So at what point does a money conversation happen? I mean, she's not going to accept me giving her money to pay off CC debt or something if she a lot of it. But even just a conversation that "hey, I want to do stuff like go out to eat or go away for a couple days, and I don't mind paying your way" without offending her? The couple times I've paid for shit for her (a $200 camping sleeping mat that weighs nothing yet is incredibly warm, and a flight to Seattle for some psychology conference) she's actively resisted me doing so. So do we just keep doing what we're doing? Or at some point do we need to talk about it? I honestly don't think she has the slightest idea on how much or little money I have/make; she really doesn't give a shit about that kind of thing insofar as you need some of it to do things. When I mentioned how many cars my brother keeps at our office (5, at last count), she was outright disgusted by it for example.
tldr: me rich, girl poor but not a gold digger in the slightest, at what point do we talk about me helping her out a bit?