I pay for everything

Tell me why I don’t like Mondays … Tell me why this guy pays for everything ….
About 7 months ago, I started dating a girl that I fell in love with. I'm 31 and she is 27. We both have serious feelings for each other and it's only getting stronger each day. I have a great time when she's around and she very well could be "the one." We spend nearly every night together in my apartment and I have no problems with that, (although once in a while, I like to have my alone time, as does she.) I am a bit old fashioned guy who likes certain romantic traditions like paying for dates. The problem I am having now is that I seem to be paying for everything even when we are not on a date. If we do regular grocery shopping, I pay. If we just grab a sandwich at a shop, I pay. I don't want to embarrass her by asking her to meet me half-way once in a while, but it's starting to get expensive. More importantly, I don't like having these feelings of resentment over money - considering it seems minor and everything else is really great. I should also mention, we both have fairly good jobs and make similar salaries. I am a generous person, but it's hard for me not to have feelings that I am being taken advantage of, even if it's not intentional. And I know it's not. She offers once in a while to pay for things, but it's always phrased in a way that puts me in an awkward position. Like, "Would you want me to pay?" Of course, I am never going to say yes to that....out of politeness. But once in a while, it would be nice for her to insist on paying for something without even asking. I want our relationship to be more of a 50/50 compromise and I am having trouble trying to communicate in a way that the message gets across without embarrassing or upsetting her. Any advice?

– Do I Have to Pay for Everything, Boston

DIHTPFE, at seven months, you should be able to tell her what you want, even if it makes her uncomfortable. At seven months, you should be able to talk about money. She can’t read minds. She can’t know that you love paying for dates -- but that you want her to go 50-50 on everything else. Your old-fashioned dating behavior is all fine and good, but those rules and gestures have to be eliminated over time in order for your relationship to leave fairy-tale land. If after a year, you can’t look at her and tell her you feel broke sometimes, there’s a problem. Dropping the old-fashioned stuff doesn’t mean there’s no more romance. It just means you’re showing some vulnerability. I can’t think of anything more romantic than that. My advice – say something like, “Every now and then, I’d love help paying for sundries and sandwiches. And I feel silly mentioning it, but I never know how to approach it in the moment. I love paying for dates – I love treating you – but the reality is, I could afford it more if you picked up some of the little stuff. And I want us to be close enough to be able to talk about uncomfortable stuff like money.” And then you hug. It won't be pleasant, but you're at seven months. It's time to drop the disingenuous pleasantries. Readers? Is his old-fashioned behavior to blame for her passiveness when it comes to paying? Is there something manipulative about the way she offers to pay? Have a good speech for DIHTPFE? Share.

– Meredith