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.

So I'm trying to figure out how to talk to him about this. It's tricky because we haven't been together that long. I have no idea how long he'll be in his current financial situation. He's had steady jobs in the past, but he did admit to me that most of his relationships have ended over money issues. The other issue is that it brings up a lot of baggage from a past relationship. I was with my ex-fiance (yeah) for six years and for most of that, I was busting ass with non-inspiring 9-to-5 jobs so that he could pursue his career as a filmmaker. In the end, we broke up because I felt like I was wasting my life away for someone else's cause. I hadn't spent enough time on personal growth and arrived in my mid-20s totally lost. We broke up, I went back to grad school, and now I'm a badass designer with a lot of confidence and a frustrating love life. WTF? Am I going to be one of those super successful, bitchy middle-aged architects with no partner but lots of employees?

—Mo Money, Mo Problems

Probably, if your life was a Meryl Streep movie, which I think we can safely assume it's not.

You should, obviously, bring this up with your boyfriend. Couch it as potential baggage from your past relationship if you must, but I honestly don't think it's necessary to share that. Actually, the fact that "most of his relationships have ended over money issues" is more of a red flag to me. Is he consistently taking advantage of his partners and not realizing it?

Deal with the problems you have today, not the ones that may or may not exist in your future Ayn Rand novel-esque scenario. The task at hand is your boyfriend's assumption that you're making enough hella scrilla to support your social lives. And it's only been a month! If you think it's awkward to bring up now, you're really going to feel put upon when six months or a year has passed and you're still subsidizing your boyfriend's bar tab. I know it's a delicate subject, and that it's a total boner killer. No one wants to feel like a cheap asshole, especially over small things, like froyo or tickets to see "Men in Black III." But if you're living beyond your means because you're too afraid to deal with the issue, that's problematic.

You're not being selfish by talking about it. So sack up and tell him (lovingly) that you can't afford to foot the dating bills all the time. Figure out a compromise that works for both of you. If this means you go out less, or he drinks less, so be it. But the better you are at talking about these kinds of issues now, the more comfortable you'll be with him in the long-term. Frankly, I'm kind of surprised it hasn't come up already. How did this dynamic get established so quickly without any kind of communication? Have you just been quietly stuffing his g-string all this time?

Another thing— two broke suitors does not a theme make. Don't assume that because you've had two pauper boyfriends some cosmic trend is going to go down for the rest of your days. It's not. And money problems are the leading cause for divorce. It's very common.

Lastly, you do care about money. Or you wouldn't have written in. And it's OK; caring about money doesn't make you a gold digger or trophy wife. It makes you financially responsible. So stop feeling guilty, be the badass that you are, and start putting your money where your mouth is.

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