Hilary DeCesare enjoyed professional success in spades, first as a Silicon Valley sales executive and later through her business as a life-transition and executive coach. But when it came to finding a new love match following a divorce , DeCesare for years ground through dating apps , sites, and other avenues without fulfillment. 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.
” 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 .
