Hilary DeCesare has achieved tremendous professional success, first as a sales executive in Silicon Valley and then as a life change coach and executive coach. But when it came to finding a new love match after her divorce, DeCesare spent years scouring dating apps, websites and other means with little satisfaction.
Then it dawned on her: she needed the same help that she would get if she were trying to achieve something in any other matter in which she was not an expert.
“I have to compete in a pickleball tournament in three weeks, what should I do? I scheduled a lesson with a pickleball coach,” says DeCesare, 55, who now manages it. Restart company from Colorado. “You don’t try to do it yourself. You go with the best.”
Enter the matchmaker.
Through a mutual friend, DeCesare met Shannon Lundgren, a Harvard MBA living in San Francisco, who had recently launched her professional matchmaking service. Shannon Circle. On the third date Lundgren arranged for her, DeCesare met her future husband, to whom she had been married for almost 11 years.
“Why do it alone when you can accelerate success and achieve it faster?” De Cesare says. “That’s what it is. Start living, and start living faster.”
Matchmaking is big business
Although it accounts for less than a quarter of the dating industry, which is estimated to be worth $4 billion in the US alone in 2024, matchmaking, not just dating coaching, but actual one-on-one matchmaking has made a significant comeback in the last two decades. Long overshadowed by dating sites and apps, the centuries-old practice has once again become the preferred option for those with the resources to pay for it and the willingness to incorporate the human dynamic of finding third-party love.
“People are becoming more comfortable outsourcing their personal lives, as if they were hiring a personal trainer at the gym or a private chef to cook for them,” says Rachel Greenwald, a US matchmaker and head of Harvard Business School. the guy whose elite services team from $10,000 to $75,000 per month and a minimum three-month commitment.
Of course, not everyone can hire a personal trainer or private chef. But even at lower levels, personal matchmaking is not the same as dating through an algorithm, and the prices—almost always thousands of dollars or more—reflect that.
Hard numbers are elusive, as I discovered when talking to several professional matchmakers about the industry’s growth. Among other things, this work does not require a license and is largely unregulated. “It’s essentially what I would call the Wild West,” Greenwald says. “It’s a lot of family businesses.”
Still, people in the know say business is booming. From about fifty individual matchmakers in the United States at the turn of the century, there are now more than 5,000, according to New York matchmaker Lisa Clampitt. only in the USA. “The industry is growing 100%,” she says.
Many clients, according to matchmakers, are tired of the online/app approach to dating or have decided that their time spent on dating is not paying dividends. Meanwhile, for some services, helicopter parents trying to pick up their adult children or advise them on dating skills themselves can account for a third or more of their business. (Parents can pay the fee, but they are not involved in the process, matchmakers say.)
Clampitt, a former social worker, got into the business. in 2000, forming the eponymous matchmaking company, which caters to New York’s wealthy elite. A couple of years later, she founded the Matchmaking Institute, now known as Global Institute of Love, which offers certifications in matchmaking and coaching, offers ethical guidelines and functions essentially as a trade association for matchmakers to share resources and best practices. Institute May 8. Global Love Conference in New York was declared the largest meeting of its kind in history.
Modern matchmaking doesn’t have much in common with its predecessor, “Your aunt has someone to meet.” Matchmakers say that while their clients are typically looking for a committed relationship, marriage is not always (or even usually) the goal, which is one reason why careful screening and interviewing is required beforehand. For example, someone who just went through a divorce may simply want to meet different people and feel good about themselves again, Greenwald says.
While most services accept clients of all backgrounds, some cater to very specific niches, be they religious, geographic, sexual, or otherwise in nature. Michal Neyster runs a service with a strong focus on Jewish coincidences in Philadelphia. “It’s an interesting microcosm for dating,” she says. “It’s a very diverse city and the birthplace of America, but it’s more of a ‘local’ city: people live here a long time, buy houses and stay loyal to their teams. I can’t tell you how many people I meet who think they already know everyone, but they don’t.”
With price guides ranging from $10,000 to $300,000 or more, matchmakers often act as concierge matchmaking services, helping clients avoid wasting time redirecting online or app profiles to possible dates. Greenwald says she might screen and interview 10 to 20 people to produce one profile that she presents to a client—a process of “curation,” as she calls it.
Elite matchmakers and their VIP clients
Elite level matchmakers, with whom Luck Company officials said they keep very short lists of customers at any given time, sometimes half a dozen or less, so they can focus on the needs of VIPs and respond quickly. (At the lower end of the cost spectrum, clients may expect more from an agency approach—less expensive, but also less personal.)
“If we do a nationwide search, it’s just a few clients at a time,” says Kat Cantrill, who runs the agency, which based in Iowa but able to search from coast to coast to find what suits the client.
Cantrill spent several years teaching women how to navigate the dating world, both online and offline, before she moved into matchmaking in 2020. She still does both, which seems to be common in the business. Some matchmakers said they also advise clients on clothing, personal branding, creating online profiles and the like.
And despite the lack of licenses and mandatory certifications, the modern matchmaking organization is clearly a commercial enterprise, the income of which can reach seven figures for the top echelon. However, for this to happen, they must be attentive to their bottom line even as they search for the right partner or successful experience for their clients.
Rachel Greenwald, for example, works only with male clients, partly because the math demands it. Many other matchmakers do the same.
“The average matchmaking customer is over 40 years old because the price is so high that younger people typically can’t afford it,” Greenwald says. “There are a lot more fantastic single women and fewer fantastic single men over the age of 40, and many of these men want to date women 10 years younger because they want to have children. So there is a shortage of women in the market.”
Matchmakers, Greenwald says, sometimes have to weigh the opportunity cost of introducing a client to a potential partner at the expense of another client whose list of required services may be much more extensive. Successful people think like lawyers in terms of the hourly rate they want to earn and the likely workload required, she said.
They must also be ruthless—empathetic in their own way. Greenwald says good matchmakers are careful, connected listeners who may end up turning away 50% or more of their potential clients simply because they don’t believe they can help those people find a match or make a positive journey.
“We are not wizards. It’s really important that people know about this business. This doesn’t mean we hand someone a menu and let them order. a la carte, whatever they want.”
On the other hand, when it works, it can be beautiful. Most matchmakers agree that “success” is in the eyes of the client, whether it’s a mutually beneficial relationship, a marriage, or simply a process of self-discovery. But, they say, seeing people click and fall in love never gets old.
“People are starting to become so successful that they end up on top of the mountain by themselves—and I find that dilemma so compelling,” says New York-based Clampitt. “I really help people learn a different skill that is completely different from being successful in business.”
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