When a Feminist Dates a Rich Guy...

dating a rich man

When you’re used to paying your own way, sharing your life with a man in the 1 percent can be a challenge.

For the better part of last year, I dated a man in a much higher socioeconomic class. And though I didn’t expect him to pay my way, sometimes circumstances necessitated it. I make a decent living as a journalist, but his position in technology sales provides him with a lifestyle I simply can’t afford to split 50/50. And this imbalance stirred in me a surprising internal conflict.

By most measures, I have done just fine in my career, providing myself a comfortable lifestyle, with a condo in the city, a vacation home at the beach, and a solid retirement account. But I earn only a fraction of what he earns. Both of my homes put together are worth far less than his house. His idea of a low bank balance is my idea of flush. While I hold the goal of hitting the $100,000 mark each year, he talks about breaking a million. There was no semblance of financial equality for us. And while some people are thrilled by the prospect a $1,500 meal at Per Se, I just couldn’t seem to relax into it.

I began dating when I was 14. My first boyfriend’s name was Bart*. We were both from middle-class families. He was 15 and liked to play golf. One summer, on sunny afternoons, I would accompany Bart at the country club, steering the golf cart and sharing French fries at the snack bar. But cart rentals and fried potatoes aren’t free, and after realizing the tab on the family account one day, Bart’s mother called my mother to say, “Bart can’t always be paying for Allison.” To which my mother replied, “Allison never leaves home without money.” Which is true to this day.

My mother taught me to never be the kind of woman who expects someone else to pay her way — at the country club or otherwise.

Cut to the beginning of my most recent romantic venture: Aware of the pitfalls of the disparity, he and I set expectations around the financial aspects of our relationship. He had, in his past, declined to date women who were unfamiliar with a world of frequent fine dining and international travel and who were unable to make a contribution to the upkeep of such pursuits, and I was quick to let him know when we paired up that I wanted to do my part.

He appreciated that I was willing to pick up the occasional dinner out or hotel room, or buy my own plane ticket. And without formal discussion, we established that if there was something special I wanted to do, such as see my favorite band in concert, I would treat us both.

Still, I struggled.

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