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?

Anna Pulley, @annapulley

April 25, 2012