Elite matchmakers—with fees up to $300K—are coaching clients on how to navigate the dating world: It gets tricky for women over 40, experts say

Then it hit her: She needed the same kind of help she would receive if she were trying to accomplish something in any other pursuit at which she wasn’t expert.

“I’m going to be in a pickleball tournament in three weeks, so what do I do? I set up a lesson with a pickleball coach,” says DeCesare, 55, who now runs her ReLaunch company from Colorado. “You don’t try to do it on your own. You go with the best.”

Enter the matchmaker.

Through a mutual acquaintance, DeCesare met Shannon Lundgren, a Harvard MBA living in San Francisco who had recently launched her professional matchmaking service, Shannon’s Circle. On the third date arranged for her by Lundgren, DeCesare met her future husband, to whom she has been married for nearly 11 years.

“Why do this on your own when you can escalate the success, get there faster?” DeCesare says. “That’s what this is. Start living, and start living faster.”

Matchmaking is big business

Though it accounts for less than a quarter of a dating industry estimated to be worth $4 billion in 2024 in the U.S. alone, matchmaking–not mere dating coaching, but actual one-to-one matchmaking–has made a pronounced comeback over the past two decades. Long relegated to the shadows of dating sites and apps, the centuries-old practice has re-emerged as a preferred option by those with the resources to pay for it and a willingness to incorporate the human dynamic of a third-party search for love.

“People have just gotten more and more comfortable with outsourcing their love life, like they would hire a personal trainer at the gym or a private chef to cook meals for them,” says Rachel Greenwald, a U.S.-based matchmaker and Harvard Business School executive fellow, whose elite services command anywhere from $10,000 to $75,000 per month and a minimum three-month commitment.

Not everyone can hire a personal trainer or private chef, of course. But even at the lower levels, personal matchmaking is not at all the same as dating via algorithm, and the prices–almost always thousands of dollars or more–reflect that.

Exact numbers are elusive, as I found when interviewing several professional matchmakers about industry growth. Among other things, there is no license required for the job, and it is largely unregulated. “It’s essentially what I would call the Wild West,” Greenwald says. “It’s a lot of mom-and-pop businesses.”

Still, say those in the know, business is booming. From perhaps fifty one-to-one matchmakers in the U.S. at the turn of the century, New York matchmaker Lisa Clampitt says, that there are now more than 5,000 in the U.S. alone. “The industry is 100% growing,” she says.

Many clients, matchmakers say, have become weary of the online/app approach to dating, or have decided that their time investment wasn’t paying dividends. For some services, meanwhile, helicopter parents trying to get their adult children matched-or counseled on dating skills themselves-can account for a third or more of their business. (The parents can pay the fee, but they don’t have input into the process, matchmakers say.)

Clampitt, a former social worker, jumped into the business in 2000 by forming her eponymous matchmaking company, which caters to New York’s wealthy elite. A couple of years later, she founded the Matchmaking Institute, now known as the Global Love Institute, which offers matchmaking and coaching certifications, suggests ethical guidelines and functions essentially as a trade association for matchmakers to share resources and best practices. The Institute’s May 8th Global Love Conference in New York was billed as the largest-ever gathering of its kind.

Modern matchmaking doesn’t have a ton in common with its “Your aunt has someone for you to meet” predecessor. Matchmakers say that while their clients are generally looking for a committed relationship, marriage isn’t always-or even usually-the goal, one reason why a thorough vetting and interview process is required up front. Someone who has just gone through a divorce, for example, may just want to meet a variety of people and feel good about themselves again, says Greenwald.

While most services take clients from all backgrounds, some work in very specific niches, whether they be religious, geographical, sexual preference or other in nature. Michal Naisteter runs a service with a heavy emphasis on Jewish matches in Philadelphia–“An interesting microcosm for dating,” she says. “It is a very diverse city and the birthplace of America, but it’s more of a ‘local’ city-people live here for a long time, buy homes, and stay loyal to their teams. I can’t tell you how many people I meet who feel like they know everyone already, but they actually don’t.”

With price estimates that range from around $10,000 to $300,000 or more, matchmakers often function as relationship concierge services, helping clients avoid the time sink of funneling online or app-based profiles into possible dates. Greenwald says she might vet and interview 10 to 20 people in order to present one profile that she presents to the client-a process of “curation” as she calls it.

Elite matchmakers and their VIP clients

Elite-level matchmakers with whom Fortune spoke said they keep very short lists of clients at any given time, sometimes half a dozen or fewer, so that they can stay focused on a VIP’s needs and respond swiftly. (At the lower end of the cost spectrum, customers can expect more of an agency approach—less expensive, but also less personal.)

“If we’re doing a nationwide search, then it’s only a few clients at a time,” says Cat Cantrill, who runs an agency that is based in Iowa but capable of looking coast to coast for a client’s right fit.

Cantrill had been coaching women on how to navigate the dating world, online and otherwise, for several years before she made the leap to matchmaking in 2020. She still does both, which appears to be common in the business. Several matchmakers said they also advise clients on clothing, personal branding, setting up online profiles and the like.

And despite the lack of licensing or mandatory certifications, modern matchmaking is very clearly a business enterprise, with earnings for the top echelon that can reach seven figures. For that to happen, though, they’ve got to be attentive to their bottom line even as they search for the right match or successful experience for their clients.

Rachel Greenwald, for example, works only with male clients in part because that’s what the math says to do. Many other matchmakers do the same.

“The average matchmaking client is over the age of 40 because the price is so high that younger people typically can’t afford it,” Greenwald says. “Over the age of 40, there is a far higher supply of fantastic single women, and a low supply of fantastic men–and a lot of those men want to date women 10 years younger because they want to have kids. So there’s this market squeeze for women.”

Matchmakers, Greenwald says, sometimes have to weigh the opportunity cost of introducing a client to a potential match at the expense of another client whose list of must-haves is perhaps much more extensive. The successful ones, she says, think like lawyers in terms of the hourly fee they want to hit and the likely workload required.

They also have to be ruthless–in their own empathetic way. Greenwald says good matchmakers are careful, connected listeners who ultimately may turn away 50% or more of their potential clients simply because they don’t believe they can help those people find a match or have a positive journey.

“We’re not magicians. That’s really important for people to know about this business. It’s not like we’re handing somebody a menu and allowing them to order a la carte, whatever they want.”

When it works, on the other hand, it can be beautiful. Most matchmakers agree that “success” is in the eye of the client, whether it is a mutually satisfying relationship, a marriage or simply a process of self-discovery. But seeing people click and fall in love, they say, never gets old.

“People start getting so successful that they’re at the top of the mountain by themselves–and I find that dilemma so compelling,” says New York’s Clampitt. “I really help people sort of move into another skill, which is completely different than success in business.”

More on dating and relationships: