I Paid a Matchmaker $250,000 to Find My Soulmate. The Result Surprised Me.

Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.Getty / Photo Illustration by Leigh Cohen4 min readDating apps have become a special kind of hell for singles. People are sick of swiping. They’re tired of the road-to-nowhere conversations and disappointing dates. For all their predictive power, algorithms simply aren’t very good at finding the one. As a result, people are dumping Tinder left and right. But they haven’t given up on love entirely. In fact, quite the opposite. After years of letting the apps play Cupid, they’re calling in the experts. Google searches for “matchmaker” more than doubled between January 2025 and 2026. And as interest in matchmaking grows, prices are climbing, too. Average fees jumped 26 percent last year. Prices vary enormously, but at the highest end of the market, finding a girlfriend can cost more than a Ferrari.For the latest installment of The Secret Lives of Men, we spoke to Henry*, a 70-year-old man from Atlanta who spent $250,000 on a matchmaker. His fee covered a year of personalized matchmaking, complete with a wardrobe consultant, dating coaches, personality tests, and a nationwide search for eligible women. After eight months and roughly ten introductions, Henry finally met someone he liked. *Name and identifying details have been changed to protect anonymity.Henry, 70, AtlantaI’m what I would call a silver fox. I’m 70 years old now, and I’m in excellent physical, mental, and financial shape. I’ve been married twice and dated plenty of women. Over the years, I’ve tried just about every way to meet someone: bars, introductions through friends, dating sites, apps. But at this stage of my life, I can afford the very best—so I decided to shell out $250,000 for a top-of-the-line matchmaker.Some people spend $250,000 on a car or $75,000 on a vacation in Positano. Others fly private. Sure, you could spend a fraction of that money, but you’d get a lesser experience. I look at matchmaking the same way. Sure, I could go on Tinder, swipe through profiles, and find women interested in me. But that’s a long process, and I don’t want to put in the same effort I did 20 or 30 years ago. I'm interested in finding someone I’m actually compatible with.I also don’t like the lack of privacy that comes with online dating. I’ve worked hard to establish a reputation in my field. I don’t particularly want a stranger, scrolling on their phone in their bathrobe, to know about my personal life. And you never know who you’ll encounter on those sites. Men used to worry about gold diggers. Nowadays, you have to worry about your safety, too.I’ve actually used cheaper matchmakers before, the kind who charge around $25,000 for a few months. Mostly, they just save you the trouble of going through dating apps yourself. They’ll find a few women on Tinder, a few more somewhere else, and send you their profiles. This time I wanted someone who would actually get to know me and put some thought into who she set me up with. That’s why I hired Sameera Sullivan. She works with only three or four clients at a time and charges $250,000 for a year of services that go far beyond what the other matchmakers offered. Those guys were like a Lexus. Sameera is a Bugatti.The first thing she did was bring in a few professionals to help with my dating profile. A wardrobe consultant went through my clothes and suggested a few changes. A photographer took my pictures, and a professional writer put together my bio. Then I had several sessions with a dating coach and took a bunch of personality tests to figure out what kind of woman I’d be most compatible with.Each date I went on helped Sameera narrow things down further. After every introduction, she’d ask both me and the woman she'd set me up with how it went. Even if we stopped seeing each other after two or three dates, she’d try to figure out why and use what she learned to make a better match next time. It’s kind of like AI. The more information she had, the better the results. The tenth woman she introduced me to ended up being the one. Sameera actually found her on LinkedIn and reached out to see if she’d be interested in going out with me.Men used to worry about gold diggers. Nowadays, you have to worry about your safety, too.We’ve been dating for almost three months now, and things are going extremely well. Everyone says we have big couples energy. She’s in her mid-50s, which is good because I look and act younger than my biological age. Our love languages match, our personalities complement each other, and I feel more compatible with her than I did with either of my former wives.One thing I really like about her is that she’s got a bit of an adventurous streak. I’m naturally pretty steady and set in my ways, but I have an adventurous side, too, and she brings it out in me. Like, the other night, we were having dinner at a Mexican restaurant, and someone mentioned there was a speakeasy downstairs. Normally, I would've said we should try it another time. But I saw her face light up, so I said, “Okay, let’s go.” We went in and had a drink. I probably wouldn’t have done that on my own.I’ve put my matchmaking contract on pause for now. If this relationship doesn’t work out, I still have about four months of service left. For now, I’m very happy with how things are going. The funniest thing about it all, though, is that the woman Sameera found for me, the one she searched all over the country for—she actually lives in my neighborhood.