How I Fell In Love With A Sugar Mama

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Woman's hand clutching hundred dollar bills
What it feels like to date a female breadwinner. Plus, how to treat a man who makes less money.

When I was working as an English professor, my fiancée ran a medium-sized company and made 15 times as much money per year as I did—before her bonus. Like many men, I'm proud and competitive. I had already accepted that I wasn't going to earn more in my lifetime than my father. Now I blanched when I wanted to take my darling to dinner: would we go to the kind of place she's used to, which I couldn't come close to affording, or would she be willing to slum it with me again?

Ultimately, she and I came to a very amicable agreement on spending: we'd alternate who paid for what and, yes, she'd take me to fancy places and I'd take her for pizza. To her credit, she never complained about picking up bills or paying part of my way if we went on a nice vacation. We were only together for two years, though, and I wonder if—over time—the differences in our lifestyles would have gotten to her... or to me. I like to think they wouldn't have, even though the chivalrous part of me would always wince when she took out her wallet. 

My guy friends didn't seem too worried about chivalry; they just asked if I was intimidated that she made so much bank. On this front, I'm happy to say no. Actually, I was proud of her—really proud. When I would travel with her on business and she'd be on the phone yelling at her (mostly male) team at 3 a.m., I'd take a few of the very lush Ritz-Carlton pillows and go sleep in the tub, smiling at how formidable she was. Can Powerful Women Find Love?

I think that a good relationship is one where both the man and the woman can teach each other things, where they alternate leadership, have mutual respect and are each truly impressed by what the other one says and does. Insecure guys are, of course, famous for wanting to date women who don't challenge them—whether they're younger, meeker, less intelligent or make less money. But where's the fun—and the long-term excitement—in that?

The trick, I think, for a successful woman trying to date a "less successful" guy (read: he makes less money or has less education) is not to make him feel that way. My ex always praised both me and my career, saying, "What's money compared to the books you read and the thoughts you get to have?" She also didn't bring her management strategy home from the office. Both genders can learn from that: the same skills that make you very effective at your job or in school might actually be damaging when used in a love relationship. At-home leadership is typically much more about humility, compromise and cooperation—not always the strong suits of type-A people. 

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