This as-told-to essay is based on a conversation with Sameera Sullivan. It has been edited for length and clarity.
As far back as high school, I loved giving people dating advice. My mom could see that I had real skill, and she encouraged me. Yet, I didn’t even know that matchmaking could be a business.
Then, in 2012, I was recruited by a matchmaking agency. Before then, I’d studied psychology and worked in education and defense. The agency thought that background would make me good at helping others find love. When I started matchmaking, I knew I’d found what I was supposed to do. But I didn’t like the way the agency operated, so I decided to go out on my own.
Since then, I’ve personally matched more than 100 couples. I focus on quality, not quantity, but my results speak for themselves, and my clients are willing to pay for my expertise. Most pay between $100,000 and $150,000. But some — the really picky, specific ones — pay $250,000. I put a lot of work in up front, so they pay before we get started.
Some successful men struggle to choose a partner
All my clients are men, most in their 40s and 50s. I think of them in two groups: some are bad pickers, who have just never been great at choosing a partner. The others are coming out of a divorce. Those guys know what they want and what they don’t.
No matter what type of guy a client is, we do a lot of psychological work and neuroscience coaching. I ask about their past relationships, identify their personality type, and help them better understand themselves so they can see red, yellow, and green flags while they’re dating.
I have a database of about 22,000 women who are willing to be matched with my clients. I generally show the client about 15 profiles. From there, we work together to choose three women for them to go on dates with.
My clients want women with purpose, but flexibility
Understanding what will make a relationship work takes a blend of skills. It’s part empathy, part rationalization, and a little common sense.
The men I work with are extremely successful and wealthy. They don’t typically care about a woman’s finances, but they want her to have something of her own that she’s passionate about. They’re willing to take care of their partner, but they don’t want someone who will mooch off them.
At the same time, they’re looking for a partner who is flexible about integrating into their lives. Most of these guys are very established where they are. Still, that’s not always the case. With one of the couples I matched recently, the man is moving interstate to where his partner lives. His lifestyle allows him to be flexible for her.
I think about how a couple’s lifestyles and ambitions will match
Each client is a unique search. I have employees whose full-time job is recruiting women, and we use proprietary software to do so. I find women on LinkedIn and at events; they also apply directly to my network.
Right now, one of my clients is 44. He’s ambivalent about having kids — most of my clients aren’t looking to have more children. He wants a woman who is not necessarily subservient, but who is softer than he is. I have to be careful about the types of profiles I show him, because he’s not looking for someone who is very career-oriented.
Other clients are looking for new adventures together. One of my couples is opening a gym together, building off the woman’s physical therapy and nursing background. Another couple — a man in construction management and a woman who owns a photography business — plan to raise cattle at a vacation home they just purchased.
I help clients be more open-minded
The clients who pay me $250,000 are the most picky and, therefore, difficult to match. It might be a guy in his 70s, looking for a woman in her 40s.
Once, I had a client say that his partner had to have an Ivy League degree. You can bet I push back on things like that. I argue and challenge my clients, and they usually thank me for it. They’re willing to listen, because they’ve hired me for my expertise. The women are sometimes less willing to be flexible, especially regarding height and age.
Dating apps have made it more difficult for people to find their partner, because there’s so much out there. On apps, the true significance of a relationship gets lost as people check boxes. You might quickly look at a profile and say, “He’s not my type,” without considering the connection you might have in person.
People get in their own way. What does it matter if you’re into brunettes, but the woman you really click with is blonde? Or, if you want to meet someone in Manhattan, but the right guy lives across the river in Jersey? You’ve got to be open-minded to love.
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