Advice: How to deal with a broke boyfriend

I've been dating this guy for about a month. He's super awesome, super sweet, lots of fun, and a pretty good match for my personality. There's just this one little thing that has been causing me great anxiety. He's got no money and doesn't seem at all ambitious or willing to take risks with his career as an artist/musician. Don't get me wrong, I totally don't care about money. I don't judge, or want to be some rich man's quiet wife. What I'm concerned about is that in the short time that we've been dating, I've paid for nearly everything. And it's not like we're living large, either. He stays at my house about three nights a week, and so I cook him dinner/feed him breakfast. When we go out, I often pay for movies, snacks, public transportation, or a drink—they're all pretty modest things, but it's definitely adding up, and I'm living on a student-debt budget.

Anna Pulley, @annapulley

June 27, 2012