The Ups and Downs of Dating a Much Wealthier Woman

Jason Hoffman's Thrillist illustration of a wealthy woman on a date with a poor boy
Jason Hoffman/Thrillist
Jason Hoffman/Thrillist

How many times in your life have you been told to marry rich?

Even as a guy, I've been counseled with that golden nugget of wisdom on more occasions than I can count. Growing up in a solidly middle-class family, money wasn't ever a pressing issue. But it wasn't exceedingly abundant, either. It was just a means to an end... typically an end that wasn't achieved until it was found in a slightly shabbier store, on sale. I knew anyone urging me on to life as a kept man at best or a gold digger at worst wasn't totally serious -- but they also weren't totally joking.

So when I tell you that I was in a relationship with a woman and money was a huge factor in our dynamic, I can understand if you assume that I was more interested in what was in her purse than what was in her head or heart. While I have to admit that I have my fair share of character flaws (vanity and arrogance coupled with spurts of crippling self-doubt -- I'm a writer, remember), I’m not quite that shallow. Just wait for the details before you make any judgments -- it's much more complicated than that. 

Actually, my issues with her money ended up being one of the things that drove us apart.  

girl with long hair

I fell for the real her

I met her at the start of my junior year of college. We had mutual friends and were both athletes at a small school, so even though I didn't know much about her at first, once she caught my eye it wasn't hard to ask around to find out more. 

"She's really sweet and smart -- and she likes you too! Go for it!" I heard over and over again from our network of friends, eager to play matchmaker. Once I found my opening, I took it, and she and I spent one of those magical college nights sharing a Thermos full of cheap vodka and cranberry juice in the corner of an apartment party, totally oblivious to everyone else in the room. 

She was stunning, and her tiny voice with its teasing Valley Girl lilt and her exotic (from my small-town Ohioan perspective) LA vegetarian sensibilities had me completely smitten.  

After stops and starts throughout that school year (all my fault -- when it comes time for the "I Was a Dumbass 21-Year-Old" article, we can get into the exact details), we began the next as a couple. She was the first girl I actually committed to at school, and I was ready for it to be serious. 

Woman climbing out of expensive car
Tyler Olson/Shutterstock

Her money was actually kind of a turn-off

By that point I knew she came from wealth. But that was nothing new: we were at a $65,000-a-year private college, and I knew many of my friends' families easily paid the full cost of tuition. Meanwhile, the bulk of mine was covered by the generous need-based aid program and loans. During my time there, I developed a bit of a chip on my shoulder about that economic chasm, although it was never something that prevented me from being friends with anyone. It was kind of a don't ask, don't tell scenario -- aside from those who really flaunted their upbringings, most people were assumed to be on roughly the same privileged page. 

The first hint that she was living with a very different set of circumstances came one day while I was eating at the school dining hall.  

"Hey, catch!" she said, approaching the table I sat at and tossing something small at me. 

After fumbling with it for a moment, I realized it was an Audi key fob. 

"OK?" I replied.

"We had the car driven out from home so now I have it here!" she exclaimed excitedly.

I was speechless. Home for her was LA, and we were in Central Ohio. I didn't have a car at school and my parents only lived about two hours north. Part of me was just as excited as she was -- but another part, deeper down, was turned off by the fact that someone had been paid to deliver a luxury car to her on her parents' dime.

That car -- a tiny black stick-shift Audi TT -- came to encapsulate the best and worst parts of our relationship. I loved it because we could spend hours in it together, driving around the small town outside the college, going on dates at hick restaurants, and killing time away from the suffocating campus. I hated it because of the looks I would get from townies when I stepped out of it, people I would often identify with more than my most privileged classmates. 

Woman with shopping bags
Syda Productions/Shutterstock

Her attachment to money consumed me

Once while we were on a jaunt we decided to go to a tattoo parlor to get her nose pierced. It was a Sunday though, and all the shops in town were closed. Later that week, she told me she was glad we were prevented from going through with it.

"I told my dad I almost did it," she said. "And he told me 'If you put a hole in your nose, you lose $10,000.'"    
I had three tattoos by then, and before the first my father had threatened to kick me out of the house. I knew he wouldn't. That she had a similar challenge and balked when a specific, quantifiable consequence could be issued bothered me to no end.

My issues came to a breaking point when I went with her to her family's Thanksgiving celebration in Philadelphia. We drove there in her car, and my nerves about meeting her parents and fitting in with people so far above my self-perceived situation hung over us like storm clouds for the whole trip. I teased her about her childhood cotillion training, sure, but I was really just terrified that I would make some terrible, low-class mistake and embarrass myself. 

I'm ashamed to say that for most of that visit, I was insufferable. It was never in public view of her family (who were incredibly gracious, lovely hosts of course), but in what little time we had alone I was sullen and silent, pouting because I felt overwhelmed by the mere idea of my presence among these impressive, educated, wealthy people.   

estranged couple

The bridge we burned was priceless

After that, things went further south. We broke up before winter break because she was studying abroad the next semester, but we decided to get back together and tried to make it work even while she was gone. After a rocky few months apart, she returned for my graduation and ended things in its aftermath. Unfortunately, I proceeded to burn the bridge between us in the following years, and we've become total strangers to one another.

In the end, that relationship failed for a multitude of reasons (like I said, I was a dumbass) -- but my attitude about her background was one of the biggest ones on my end. It became an almost toxic resentment for no clear reason: on the whole, she was a lovely, grounded person, who worked a campus job, earned her own money, and lived within her means as much as any college student. She was kind, and generous, and aside from the car (which I later found out had been purchased used from a friend specially for her 16th birthday), she made no blatant outward displays of her wealth.

The real issue, then, was that I placed a higher value on class and money than I ever should have. I grouped a girl that I loved -- and yes, through all that, I did love her -- with an unattainable concept of wealth and power that was just that: a concept. I clung to my issues with her money in an ass-backward attempt to mask my own insecurities.

Yes, there are stratified tiers within society. But from my experience, when it comes to interpersonal relationships and someone you really care about, those boundaries only exist insofar as you allow them to.

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Brett Williams is a writer in New York. Yes, he is well aware that he sucks, thank you. Follow him: @bdwilliams910.