Hilary DeCesare enjoyed professional success in spades, first as a sales manager in Silicon Valley and later in her business as a life transition and executive coach. But when it came to finding a new love match after a divorce, DeCesare spent years searching dating apps, sites and other avenues without satisfaction.
Then it dawned on her: she needed the same kind of help she would get if she were trying to achieve something in another endeavor in which she was not an expert.
“I’m competing in a pickleball tournament in three weeks, so what should I do? I set up a class with a pickleball coach,” said DeCesare, 55, who now manages her Restart Colorado company. “You don’t try to do it alone. You hang out with the best.”
Enter the matchmaker.
Through a mutual acquaintance, DeCesare met Shannon Lundgren, a Harvard MBA who lives in San Francisco and recently launched her professional matchmaking service. Shannon’s circle. On the third date Lundgren arranged for her, DeCesare met her future husband, to whom she has been married for almost eleven years.
“Why only do this when you can escalate success and get there faster?” says DeCesare. “That’s what this is. Start living and start living faster.”
Matchmaking is big business
Although it represents less than a quarter of the dating industry, which is estimated to be worth $4 billion in the US alone by 2024, matchmaking – and not just dating coaching, but actual one-on-one matchmaking has made a pronounced comeback in the last twenty years. Long relegated to the shadows of dating sites and apps, the age-old practice has re-emerged as a preferred option of those with the means to pay for it and the willingness to integrate the human dynamics of a third-party search for love.
“People are increasingly comfortable with outsourcing their love lives, like hiring a personal trainer at the gym or a private chef to cook meals for them,” says Rachel Greenwald, a US-based matchmaker and director of the Harvard Business School. guy, whose elite services assignment anywhere 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 the lower levels, in-person matchmaking isn’t at all the same as algorithmic dating, and the prices — almost always thousands of dollars or more — reflect that.
Exact numbers are elusive, as I discovered when I interviewed several professional matchmakers about the industry’s growth. Among other things, the job does not require a permit, and it is largely unregulated. “It’s essentially what I would call the Wild West,” says Greenwald. “They’re a lot of mom-and-pop businesses.”
Still, say those in the know, business is booming. From perhaps 50 one-on-one matchmakers in the US at the turn of the century, says New York matchmaker Lisa Clampitt, there are now more than 5,000 in the US alone. “The sector is growing at 100%,” she says.
Many clients, matchmakers say, have grown tired of the online/app approach to dating, or have decided their time investment isn’t paying off. For some services, helicopter parents trying to match their adult children, or providing advice on dating skills themselves, can account for a third or more of their revenue. (The parents can pay the fee, but they have no input in the process, matchmakers say.)
Clampitt, a former social worker, entered the business in 2000 by forming her eponymous name matchmaking company, which focuses on New York’s wealthy elite. A few years later, she founded the Matchmaking Institute, now known as the Global love institute, which offers matchmaking and coaching certifications, sets ethical guidelines and essentially functions as a trade association for matchmakers to share resources and best practices. The Institute is May 8 Global Love Conference in New York was billed as the largest gathering of its kind ever.
Modern matchmaking has little in common with its predecessor ‘Your aunt has someone you can meet’. Matchmakers say that while their clients are generally looking for a committed relationship, marriage is not always (or even usually) the goal, one reason why a thorough screening and interview process is required beforehand. For example, someone who’s just gone through a divorce might just want to meet a variety of people and feel good about themselves again, Greenwald says.
While most services take clients from all backgrounds, some work in very specific niches, whether these are religious, geographical, sexual preference or something else in nature. Michal Naisteter runs a service with a heavy emphasis on Jewish matches in Philadelphia — “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 have lived here for a long time, buy houses and stay loyal to their teams. I can’t tell you how many people I meet who feel like they already know everyone, but in reality they don’t.”
With price estimates ranging from around $10,000 to $300,000 or more, matchmakers often act as relationship concierge services, allowing clients to avoid wasting time funneling online or app-based profiles to potential dates. Greenwald says she might research and interview 10 to 20 people to create 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 Sprak said they keep very short lists of customers at any given time, sometimes half a dozen or less, so they can focus on a VIP’s needs and respond quickly. (At the lower end of the cost spectrum, customers can expect more of an agency approach: less expensive, but also less personal.)
“When we search nationally, it’s only a few clients at a time,” says Cat Cantrill, who runs an agency that based in Iowa but able to search coast to coast for the right fit for a customer.
Cantrill has been coaching women on how to navigate the dating world, online and otherwise, for several years before making the leap into matchmaking in 2020. She still does both, which seems to be common in the industry. Various matchmakers also indicate that they advise customers on clothing, personal branding, setting up online profiles and the like.
And despite the lack of licenses or mandatory certifications, modern matchmaking is clearly a business venture, with top-tier revenues reaching seven figures. For that to happen, however, they must be attentive to their bottom line, even as they look for the right match or successful experience for their customers.
For example, Rachel Greenwald only works with male clients in part because the math says so. Many other matchmakers do the same.
“The average matchmaking customer is over 40 because the price is so high that younger people typically can’t afford it,” says Greenwald. “Over the age of 40, there is a much higher supply of fantastic single women, and a low supply of fantastic men – and many of those men want to date women ten years younger because they want to have children. So there is market pressure 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 may be much more extensive. The successful ones, she says, think like lawyers in terms of the hourly rate they want to achieve and the likely workload required.
They must also be ruthless – in their own empathetic way. Greenwald says good matchmakers are cautious, 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 have a positive journey.
“We are not magicians. It is very important that people know about this company. It’s not like we hand someone a menu and give them the opportunity to order a la carte, whatever they want.”
On the other hand, if it works, it can be beautiful. Most matchmakers agree that “success” lies in the eyes of the client, whether it’s a mutually satisfying relationship, marriage, or simply a process of self-discovery. But watching people click and fall in love, they say, never gets boring.
“People are starting to become so successful that they’re at the top of the mountain on their own – and I find that dilemma so compelling,” says Clampitt from New York. “I really help people gain another skill, which is completely different from success in business.”
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