What Happens When A Feminist Dates A Rich Guy

Illustrated by Jasmin Valcourt.
By Allison Hatfield

When you're used to paying your own way, sharing your life with a man in the 1% 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 of 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 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.

Illustrated by Jasmin Valcourt.
The transparency we shared didn't override the deeply ingrained feminist messaging. It flashes like a neon sign through my mind almost all the time. Some of my friends simply wouldn't go out with a guy who wasn't prepared to fund every dime of every date, but as a ferociously independent woman I value parity over chivalry and experienced a wave of anxiety every time a restaurant check came. Sometimes I was so uneasy that I hid in the bathroom.

I did realize, however, that if he and I were going to play together — if I was going to give us a chance to fall in love — there was going to be an imbalance that inflamed my sense of myself as a self-sustaining woman. There was just no way around that. Should he go on vacation alone? No, that's silly. Should I ride in coach while he travels in first class? Of course not. He was fine with the financial arrangement, but I was often conflicted.

There were limits, though, to what I accepted. For example, when we returned from a weeklong vacation to California, I discovered that the bill to board my pets was more than I had anticipated. It was my fault: I hadn't communicated clearly with the kennel about my choices, and the cost was about twice as much as I'd planned. Hearing of my surprise, he generously offered to split the cost with me. I refused. My pets, like my car and my mortgage and my health insurance, are my responsibility.

I take great pride in taking care of myself. I always have. But, when you date a man who can take care of you better than you can take care of yourself where matters of money are concerned, sometimes it's okay to set pride aside. At least I think it is.

*Not his real name.

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