Advice: Is a relationship doomed when the woman earns more than the man?

I make considerably more money than my boyfriend. He makes a decent living too, but hasn't been nearly as ambitious in his career as I have been and has talked about wanting a new job for years. He says it doesn't bother him that I make more, but I think it does. I know he wouldn't want his friends to know and he still insists on paying for things. How can I make him feel better about this? And, sometimes I do judge him, not because he makes less money than me but that he hasn't tried to go farther in his career. I've tried to encourage him to look for a new job and have offered to help with his resume, but he just keeps avoiding it. How do I make sure this doesn't drive us apart?

—Money problems

If he wants to pay for things and you know it's not going to, for instance, bankrupt your future children's college education fund, let him pay. It doesn't have to be a big deal, especially if he makes a "decent living," as you said. Emphasizing the financial disparity in your relationship over and over will only breed resentment. I never have much moolah, but I like to do nice things for people I date. It makes me happy to take someone out for froyo or for a Bloomin Onion at Outback.

I'd bet money, but not a lot (see previous paragraph), that it makes your boyfriend feel good to foot the bill even if you're winning most of the bread. Has he actually expressed resentment or ill-will about the hella scrilla you make or are you going off assumptions? Like, has he said, "This makes me feel emasculated"? If so, then you should sit down and have an honest conversation about needs and expectations, because these are concerns that are not actually about money. Also, why would he tell his friends how much each of you make? Do men get together and brag about how much more money they make than their girlfriends? If so, that would really explain a lot about the persistence of the wage gap.

His career ambition is another story, and actually seems to be affecting your outlook on the financial situation as a whole. Are you annoyed that he complains about his job but never does anything to change it? If so, try not to look at the situation as a permanent state of affairs. Maybe he just needs a little more time to get his CEO legs. Money comes and goes. Careers change. People get laid off and get promotions. You've done your part to encourage him and to offer your support, but that's as far as you can go. We all know the expression: You can lead a horse to water, but you can't make it [bleeping] finish that screenplay already. I'd ask yourself this: Is compatibility more important than ambition in your relationship? What if he does get that swank job and has to start working 70-hour weeks?

Focus instead on what he does contribute to your relationship, not what he doesn't. And on how you can both be there for each other. Money can't be the sole basis for equality in a relationship. As I've said before, money doesn't tell you a damn thingabout someone's worth. If you treat each other with admiration and respect, and show how much you appreciate each other, then money shouldn't be the wedge that drives you apart. Dollars and sense, you know?

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