Sep 06

I Thought Dating a Millionaire Would Make Me Happy. I Was Wrong

Made of money

In my mid-twenties, I noticed a curious phenomenon: Friends would start dating someone, and suddenly, they would combine salaries and become “DINKS” — double-income, no kids. This shift gave them a lot more spending flexibility; suddenly they could go on luxe vacations, spring for an apartment in a doorman building, or not give a second thought to nights out at expensive restaurants and cocktail bars. But it wasn’t just the luxury of having two incomes. It was the fact that many of my friends, by pure coincidence, ended up dating incredibly wealthy people.


In a city like New York City, the wildly rich often rub elbows with the just getting by. Money in Manhattan is everywhere, and as friends began to move from cramped shared apartments into roomy penthouse-style lairs with elevators, doormen, and addresses that raised eyebrows, it made me wonder what it might be like to actually not have to worry about money. In my early twenties, my core group of friends were all young twenty-somethings who made entry-level wages in journalism, education, and non-profit work. A $5 beer was a splurge; a $15 pasta plate saved for a birthday or big-deal promotion celebration. But as one friend dated a hedge fund founder, and another dated a wealthy startup entrepreneur, I wondered at what point they realized how much wealth they were coupling up with — and if there was a way I could capture some of that savviness in my own dating life.


Was “what do you do?” code for “how much do you make?” Was the choice of a restaurant with a $$$$$ rating a romantic gesture or an aggressive attempt to prove worth? And what would it be like to actively go after someone who made far, far more cash than I did?


In some ways, I thought dating someone several tax brackets above me might make me happier, or more secure. I had gone on plenty of dates with people who made a similar amount of money as me, and so often, the night deteriorated into both of us trading anxieties about our roommates, jobs, and futures. When I went out with friends who had money, that anxiety was lifted. Why not have another round of drinks? Sure, let’s have appetizers and dessert. Don’t worry, let’s grab a cab. Money — having it, using it, not worrying about it — was alluring.  


The more I saw evidence of this, the more I wondered what it would be like to date someone who truly didn’t have to worry about cash. Like it or not money — how much did you have, how much would you have if you continued on the same professional track you were on — was a third wheel in so many dating encounters. Why not just put it out in the open and say to the universe (or that I wanted to meet someone fabulously wealthy, and I wasn’t afraid to admit it?


And, the universe listened. Because just about three weeks after I made that decision, but unsure how to spell that out on a dating profile in a way that would neatly fit in between “likes surfing” and “likes dogs, but doesn’t have any,”  I met Norm*, a poker buddy of a friend’s husband who hosted a Labor Day barbecue at his house. Sounds like NBD, but the fact that he had a house in Manhattan when families that make over six figures often cram themselves into one-bedrooms, was impressive. During the dinner, Norm  showed us his collection of rare whiskies (“this one was made when Abraham Lincoln was born!”) and casually pointed out a Rothko painting in his living room. I found out his daughters from his first marriage were the same age as me. As he peppered mentions of first class flights, expensive getaways to Aspen, and the pied-a-terre he owned on the strip in Vegas into conversation, I knew I wanted to see if I could go on a date with him. There was something alluring about the casual way he showcased his wealth, as if he was just as attracted to it as I was. I liked the fact that he had made his money, wasn’t afraid to show off, and that he also seemed self-effacing; almost a little bit shy. Still, up close, it was clear that money was attractive. He knew it. And so did I.


After the barbecue, I sent Norm a handwritten thank you note, knowing full well that I was flirting with my rich guy fantasy — and a real life rich guy. He wrote back, and we went on our first date to Nobu, a trendy, expensive sushi restaurant with four dollar signs on Yelp, where a single piece of sashimi easily cost double digits.


And that was where I realized the rules of dating “someone rich” were completely different than dating someone who made a similar income to you. Five minutes before I met him, I got a text: I told the hostess to look for the woman with the brilliant red hair. I cringed. I had just changed my hair back to its natural brown. As soon as I walked in and mumbled Norm’s name, the hostess scowled: She clearly thought I was a gold digger. I felt like I had been caught as a young woman dating a rich older guy. And while that was what I was, suddenly, I had qualms about how it looked to others. I also felt out of place: I liked the cheap hole-in-the-wall bars I would usually meet my dates; I didn’t need to be talked up by my date to some hostess he was trying to impress. It was one thing to accidentally realize the person you were dating had a lot of money. It was another to orchestrate the whole arrangement.  


But I kept it going. One night at his house, he casually showed me the $30,000 he kept in his sock drawer, just in case. I had never seen that much cash, and so many thoughts went through my mind. Just a fraction of that money could help me pay off my credit cards, could give me the financial stability I had never truly felt in my adult life. He took out a few hundred dollar bills, casually flicking them back and forth.


“Do you need anything?”


I shook my head.


In the three or so months we dated, we went to some of the best restaurants in the city. Norm casually asked me on trips — would you like to go to Vegas for the weekend?as easily as previous dates dropped happy hour invites. And when I declined a suggestion, he would bribe me. One time, he asked if I could come over on a Friday evening after work. The day had been stressful; all I wanted to do was watch Netflix solo. He insisted, offering up an iPad as a reward for coming over.


An iPad? Really? Sure, it would be nice, but a whole lot of feelings came up. First, why did he assume I didn’t already have one? Second, would he really want to hang out with someone who was only hanging out with him for his electronics? Third, no.


Ultimately that — and the age difference — was the reason why I called things off. I’m glad I had the experience, but I was so excited to go back to dating people who understood my approach to money. Money can’t make a relationship. And turns out, Abraham Lincoln-era whiskey sucks.


Now I’m single, and am financially secure enough to buy overpriced sashimi on my own, thank you very much,  I’d be lying if I said I still didn’t fantasize about his cash drawer. But now, instead of dating someone who has one, my goal is to have a my own bundle of my own G’s alongside my socks.


The downsides of dating rich

I’m not the only one who found dating wealthy people to be… complicated. Five women share their experiences:


“When I dated a man with money, all my friends assumed I was rich. I wasn’t! His parents were funding his life and his businesses, so he didn’t have to worry about money, but it’s not like that cash transferred over to me. If anything, dating him made me go into debt because I felt I had to spend to keep up with him, buying nice clothes, getting regular blowouts, and insisting on paying my way if we, say, went to a pricey workout class together. I didn’t want to seem like a gold digger, so I overspent because I just didn’t want to say, “hey, I can’t afford this.” — Shari, 38


“Pretty early on in our relationship, I googled my now-husband and learned that his father made about $15 million each year. He never told me about any of this, or made it sound like he grew up wealthy, and knowing this about him — but not seeing him volunteer the info — was pretty weird. It was only once we began talking about moving in together that he gave me his full financial picture, which was that he had this huge security net to fall back on, but he didn’t want to depend on his parents. It was stressful for him. I appreciated his honesty, but it was just weird how money became this third entity in our relationship.” — Erin, 29


“I dated an heiress for about six months who tried to manipulate me with her money.  She would buy me expensive presents, even when I said I didn’t want anything, and then act put out if I was anything less than grateful. I began to dread her ““I have a surprise for you” texts. But it was also sad, because I think she truly didn’t realize that she had so much to offer beyond money. — Rebecca, 32


“I’ve been dating a wealthy man for about six months, and I have mixed feelings. It was something I never set out to do, and then I ended up meeting a guy at a party who owns a chain of businesses and has three apartments, a driver, and all these trappings of wealth. He seems to think everything can be solved with money, which I hate, and he doesn’t understand that I like paying for things — it’s a point of pride. For example, I mentioned that a friend of mine joined The Wing, this social club and coworking space, which has an annual membership fee of $2,500. He immediately offered to pay for my membership, and was offended when I declined. I know $2,500 is nothing to him, so then I was like, why didn’t I accept it, when the cost is actually a big deal to me. It’s just confusing.” — Adrienne, 27


“I once dated a guy who worked in finance and clearly had money, because he owned a two-bedroom apartment with a terrace in a luxury building. He always wanted to drive out to the Hamptons to “look at real estate,” and then would suggest splitting a check or forget his credit card when we stopped at a cafe or for coffee. I didn’t mind paying the bill sometimes, but it happened so often that it felt like there was something else going on. At the very least, he was oblivious to what it was like to have to watch spending. One time, we went to the grocery store to buy ingredients to cook dinner. He threw things in the cart without looking at prices, and then, when we went to check out and the bill came to $158, he asked if I minded getting it. To me, $158 is groceries for a month, not a meal! I wish I could say we talked it out, but the $158 dinner was the last time I saw him. I couldn’t deal.” — Stacy, 26


*Name has been changed


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