RELATIONSHIPS

Dating Rich Guys Isn’t All It’s Cracked Up to Be

Marta Levchenko
3 min readMay 8, 2023
a man in a suit adjusting his tie
Photo by Ruthson Zimmerman on Unsplash

“There’s nothing wrong with dating for money.”

That’s what Amy Andersen, founder of a successful matchmaking service established in 2003 and crowned as the “Cupid of Silicon Valley,” said about her long career setting people up with millionaires in an article published in CNBC’s Make It.

We’re a long way from 2003 now, and it seems to be an open secret that a lot of people have taken a new approach to romance that’s more than just about finding love. Women in particular are being candid about dating rich guys. Honestly, can we blame them?

But what might sound like a good idea for a modern, go-getting woman can also have its drawbacks. Sometimes, landing yourself a guy who’s loaded can still spell trouble.

Power Imbalance

If he’s rich, then he’s definitely got some Opinions.

Dating a guy who’s either an old money scion or a self-made man who’s built his empire from the ground up can be challenging if you’re a woman who likes being in charge of things. He might not like feeling inferior or not always having the upper hand, so speaking your mind or defending your point in an argument will be hard.

When you’re with someone who’s wealthier than you, a certain imbalance in the power dynamics within the relationship will most likely be in place.

You’ll have to be prepared for that and establish a way to communicate with them honestly, so that you don’t lose your voice even while you’re still dating.

Financial Dependence

Even if you’re not strapped for cash and hold a job of your own, there’s still a difference between having disposable income and treating a thousand dollars as loose change.

Dating a rich guy might tempt you to be financially dependent on him, and that limits the things you can do and even the places you can go to. Not only will you be in danger of feeling like you owe him, there’ll also be a lot of serious problems in the long run should you decide to end things.

This can be quite a challenge, but if your Mr. Right is also wealthy, you’ll have to be even more self-aware of your financial capacity.

While you’re still dating, continue to be in charge of your personal budget, establish gift-giving boundaries, and take the initiative to plan inexpensive dating activities where you’ll feel comfortable financing the whole thing.

Oh, and don’t quit your day job.

High Expectations

The lifestyle of wealthy people has its own demands.

Being in a relationship with a man who belongs to a higher social class than your own might force you to change a lot of things about yourself in order to fit into his world. You may be asked to dress differently, talk a certain way, and maybe even adjust parts of your personality.

Just as women are accused of having high standards, rich guys can also have specific expectations when it comes to their romantic partners.

You might think, Well, that’s just about any other relationship right there. And you’d be right. All relationships, no matter the tax bracket, demand adjustments, anyway. It’s just that there are some adjustments that we’re more comfortable with than most.

So it’s advisable to see it like any other relationship: know within yourself if you’re up for it. If you’re not, it’s best to be upfront about it as early as possible.

Bad Optics

There’s not a lot of ways to phrase this one in a delicate way. Most people will be judging women who date for money.

When you’re with a guy who obviously looks like he’s rich, you might be tagged with some nasty names to try and demean your character. “Gold digger,” and “social climber,” are just a few examples of labels you’ll probably be familiar with over the course of your relationship.

If you’re sensitive to people’s opinions and what others have to say about your life, dating a rich guy will definitely put you in a lot of uncomfortable situations.

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