Question for y'all:
I've been going out with people who have less money than I do. I have a lot of debt, yes, but still have a pretty decent disposable income (finally!). Part of me still thinks that they should pick up the check, at least initially, but is that wrong of me? $50-100 is much more to them than it is to me, and I definitely get feedback on it, even if it is subtle and not necessarily negative. e.g. Manpris joked how his friends were advising him on cheap dates and suggested mcdonalds. Hot Bartender joked about my picking up the tab for the second set of drinks. And let's not forget Long Haired (under)Grad Student who told me "I don't mind that you're rich."
I don't like feeling guilty about the money they spend on me on a date. I would be willing to buy for a fancy date, but feel like I shouldn't have to for a standard first or second date, KWIM? Drinks, on them. Movie, on them. Dinner at Dahlia Lounge, on me! Or use some creativity -- I love a cheap hamburger joint if it's fun. I don't know, I don't want to come across as bitchy or self-entitled, but don't know how to tell them that it's okay to take me some place not expensive (what girl doesn't love a picnic or bottle of wine under the stars) but not to make me feel acutely how much money I'm costing them.
On a side note, I had a great first date tonight. Hot Bartender. The above was really the only down side.