I’ve got a question for you. I’ve been dating a woman for about a month, and things are going great — with one big problem. She makes WAY more money than I do. I’m not generally sensitive about my salary, but this is nuts. She could buy me ten times over. I feel intimidated by how powerful and driven she is. I feel like I’ll probably never attain the level of success that she has — if we ever get married, I’ll always be the secondary bread-winner. The supplemental income. The runt. What shou

You’re in a tough spot. Women like guys with money — it’s the whole point of getting rich. If this woman makes more than you and still likes you, it only means one thing: There’s something wrong with her. If this woman likes you despite being way more successful than you, how low do you think she would stoop? Would she date an inner-city High School teacher? A starving artist? A hobo? If the amount of money you make doesn’t factor into the way this woman feels about you

You never want to date a woman that can’t do any better than you, Ronald. If you’re the best this woman can get and you’re not a billionaire male model that runs a charity for orphaned puppies, it means you’re settling. You’ll constantly wonder if you could potentially be dating someone that makes even more money than this woman. And who wants that kind of pressure? Is she going to pay with that dog? You should dump this woman — but not before you ride the gravy train a little longer.

Have her take you out to some nice dinners and buy you a few suits. Invite her to take you to Monaco for a weekend to gamble. Let her tag along with you on a trip to Moscow to pick up a few Fabergé eggs. Don’t feel sleazy for exploiting this woman with the intention of dumping her soon after, Ronald. Remember, you’re teaching her a valuable lesson: She can’t do any better, but she can do a whole lot worse.