In Online Dating, Being an Entrepreneur Is an Advantage–for One Group, at Least

It turns out that entrepreneurship can be sexy.

According to data from dating website OkCupid, more people have been proudly owning the title “entrepreneur” while looking for love online this past year, says Melissa Hobley, the company’s global chief marketing officer. And for some, it’s a clear advantage.

From July 2020 to July 2021, use of the terms “entrepreneur” and “self-employed” on U.S. OkCupid profiles increased by 10 percent. And users who identify themselves as entrepreneurs in their profiles have a better chance of getting a match’s phone number, according to the company.

“Dating apps are just a reflection of what’s happening culturally at large,” says Damona Hoffman, OkCupid’s resident dating coach. Hoffman attributes this uptick to the pandemic, which has spurred more people to start their own businesses, either by choice or by necessity. 

To determine whether entrepreneurs were more successful than non-entrepreneurs at making real connections on OkCupid, the company’s data scientists looked at rates of “contact exchange”–when users swap phone numbers or email addresses with matches, which typically means they’re going on a date. Specifically, the company compared the contact exchange rates of profiles that mentioned “entrepreneur” or “self-employed” with the rates of profiles that didn’t. Sure enough, the entrepreneurs were getting more numbers.

“It’s lonely being an entrepreneur,” Hobley says. “So if it’s going to help you be a little more likely to find love, then that’s a pretty great thing.”

But there may be a catch: If you’re a woman, being open about your entrepreneurial career might give you a better chance of moving to the next level with a match, but if you’re a man, it might actually reduce your likelihood of making an initial connection. Women who mention “entrepreneur” and “self-employed” on their profiles have a nearly 50 percent higher rate of conversations than women who don’t, according to OkCupid, but men who use those terms have a 13 percent lower rate of conversations than men who don’t. (OkCupid defines a “conversation” as two responses per person.)

It’s hard to know why men who identify themselves as “entrepreneurs” or “self-employed” are at an apparent disadvantage. But according to Hoffman, when a man calls himself an entrepreneur, “women sometimes read that to mean not gainfully employed or not satisfied with [his] current career path,” which signals that he could be a drain on his partner’s finances. “This is a vestige of our old relationship culture in which women needed to partner with men for their livelihood,” she says, and the norm has persisted despite women’s success in the workplace and in entrepreneurship.

Indeed, OkCupid has heard from some straight women that they’re less likely to trust men who call themselves entrepreneurs, according to Hobley. That’s partly because men have more of a reputation for stretching the truth on dating apps, she says, and partly because it’s not clear what defines an entrepreneur.

“Does that mean you have an eBay store with baseball cards?” she says. “Does that mean you are on Series C of your startup and you’re talking to Kleiner Perkins?” 

Self-identified straight men, on the other hand, seem to be less skeptical. “With women saying that [they’re entrepreneurs], men are really leaning into that, and are literally turned on,” Hobley says. 

The OkCupid data shouldn’t dissuade founders of any gender from talking about their careers with potential dates, says Hoffman. “If you are truly an entrepreneur, proudly say that on the app, and use specifics that help people understand it’s not just a fantasy or side hustle–it’s your livelihood and your passion,” she says. “Those who are inspired by that will lean in; those who are repelled by it weren’t for you in the first place.”