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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