What I Learned From Dating a Billionaire

Jason Hoffman/Thrillist

At some point in every woman’s life, she fantasizes about what it might be like to date a super-rich guy. How could we not? We role-play from a very young age that we’re all princesses, waiting for our Prince Charmings to roll up in a diamond-studded carriage, whisk us away to a castle, and live happily ever after without doing a day of work. Right?

Wrong. Having strolled around the block in those obstinate glass slippers, I’m convinced that more often than not real-world Cinderellas end up pill-popping trophy wives worthy of a spot on Real Housewives. Or they end up jaded -- and single -- like me. I was 22 when I met a billionaire bachelor twice my age at a charity event. We only dated for a few months, but that was plenty of time to learn several important lessons about what it’s actually like to date so drastically outside of your own tax bracket.


Like Jon Snow, you know nothing

After a few flirty phone calls, I wanted to know everything about the billionaire. So of course, I started Googling. I thought I had a pretty good idea about his character from interviews and TV appearances. He came off as humble and down to earth. What I eventually learned is that he, like many powerful and influential people, just has a really good PR team.

Nothing will prepare you for the ego

I went in thinking, “This guy’s a philanthropist who worked his way up from nothing. There’s no way he can be an arrogant prick.” But now I think that multiple zeros in a bank account and a gargantuan mansion can make anybody cocky.

He was a good person, but so full of himself -- going on about his garden parties, invites to celebrity weddings, and a famous ex-girlfriend it was really time to move on from. At first I was impressed, but then it all got really tedious. That’s why I’ll never again go out with someone who a) doesn’t let me talk and b) is so full of shit.

Flickr/Ben Raynal

You’ll become a wallflower

The billionaire had a lot of problems his money couldn’t fix and not many people he trusted to talk about them with. All those problems fell on me. And I was better than a therapist, because there was sex involved.

Being so young and naive, I stuck around thinking I was on an adventure with him and that I could learn a lot from his success. But soon I realized it was the opposite: this relationship was all about him. I, on the other hand, was fast becoming a shadow of my usual, outgoing self.

Old billionaires still act like old people

The billionaire had a daughter my age, which I told myself didn’t make a difference. Newsflash: it really did. Being so much older than me, we were in different places in our lives. I wanted to watch live music and sit at cocktail bars. He wanted to fall asleep with a bowl of popcorn and satellite TV.

Sometimes age gaps can work, but this wasn’t one of those times.


Money will always be the elephant in the room

For a billionaire, this guy was extremely stingy. I knew it was over when I saw him reheat half a cup of Starbucks coffee in the microwave and drink it. 

I wasn’t with him for the money, but knowing he had so much and wouldn’t spend it was a serious turn-off. We kissed and held hands in public, but never went to a fancy restaurant. After our breakup, knowing he took a friend of a friend out on a few ritzy dates made me totally neurotic. Money was the elephant in his floor-to-ceiling-windowed living room. It had so much to do with everything going on; but if I were to bring it up, I’d just look like a gold digger.

You’ll be called a gold digger. No matter what.

When I’ve told friends this story, the reactions range from giggling to disgust. I’m a grounded, confident person now and consider the whole thing kind of embarrassing. I was messed up after a bad breakup and at that time I probably would’ve fawned over anyone who paid attention to me. But of course, it had to be that billionaire! It’s easy for anyone to hear my story and just say I was with an old guy for his money. 

Flickr/Caitlin Regan

Future boyfriends will be highly uncomfortable

I’ve dated a couple of guys who really freaked out about this. “How could you have been with someone like that?” they want to know; or, “How could you have been so naive?” That’s why these days I keep my mouth shut about it, and I wish that someone would’ve bestowed some wisdom upon me.

It’s a mistake you won’t easily forget

A rich and famous ex is the most difficult to get away from. We’re not Facebook friends anymore, but this guy still comes up in my feed now and then. Knowing everything I know about him now, I can’t help but cringe.

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Sophia Glass is a San Francisco-based writer for Thrillist whose feet will never fit into another pair of glass slippers.