“They listen, they compliment, they pay attention—that is kind of what flirtation is. Some say up front that they are not interested and change the subject right away.The person feels very understood, so they’re going to get a crush.”Practically every relationship expert is familiar with navigating this “blurry emotional boundary,” as Ms. Other matchmakers, however, who grapple with their own feelings for clients, have trysts—and more than a few have gotten married.It was going great, she said, until he freaked out and disappeared.Later, he got back in touch, apologized and offered to fly her down to Miami.“They’ll want to text us, check in and have banter,” said Erika Christensen, who founded Train Spottings, the service in which matchmakers roam the subways searching for potential mates. We try to establish boundaries early and often.”The Train Spottings method can be particularly troubling. “It’s sort of frustrating because it’s a lot of work to find single people for other people, and then to have someone sign up and have it become seemingly useless after that is, like, so annoying.”Other clients, though, are more up front about their intentions. C., said she would wear her wedding ring in client meetings to fend off grabby guys. “It was probably the easiest match we ever had,” she said.Kady Grant, a 25-year-old employee of the unconventional company, said she initially went up to strangers and asked them cold if they were single, which gave the impression she was interested in them. One day, though, she forgot it—the only day, in fact—and met the man who would become her husband. “I had the privilege of learning everything about him that most women would want to know about their date without having to go through that awkward first-date conversation.”The age of the haimish, old-world matchmaker epitomized by Yenta in Fiddler on the Roof, is long gone.Spindel, an attractive, ebullient 28-year-old brunette. “I have this much free time.” But even if she weren’t so busy, cavorting with clients would be unprofessional, by her estimation.That’s why she deploys the ring, a kind of work-time Lisa Clampitt, the founder of the New York-based Matchmaking Institute. Others say they are in a relationship, whether true or false.
“Matchmakers aren’t robots,” said Amy Laurent, a relationship expert and Bravo reality TV star.Sometimes she is, she said—and often potential clients will email her about going out after she hands them her business card. He asked, as many do in the introductory conversation, if she was single. Today’s entrepreneurial love peddlers often rely on their own looks and charisma to build their brand and attract clients—though maybe not in the way they’d imagined.“The distraction of me being an attractive woman gets in the way of doing the job,” said Carmelia Ray, a veteran matchmaker in Toronto and the author of Finding the One: The A-Z Secrets to Attracting and Keeping Your Soul Mate. Spindel, who has worked in the business for 24 years, says she’s responsible for 1,517 of them—“or something like that”—and sees herself as the city’s unmatched ’maker.“They’re single girls who’ve been single for a very long time, so they figure, ‘Why not? They wear nice suits, drive expensive cars and have courtside seats at NBA games. Ferman, whose story is somewhat legendary in the matchmaking community, met her husband, Gil, in 1990 when he was the director of Great Expectations, the dating service, in St. “You’re not really supposed to date your own clients, it’s kind of an unspoken rule, but it happens all the time,” said Ms.Ferman, who estimated that 30 to 40 percent of married matchmakers around the country have found their spouses through their own services.He misinterpreted the nature of the meeting, later telling the woman he’d been set up with that he didn’t want to see her anymore because he was dating his matchmaker. Goldman said, “because she was just about to kill me.”Men, as is their wont, are sneaky, and it can take a while to catch on to clients who aren’t direct.Some even come to see their matchmakers as surrogate girlfriends.Sales, after all, is a kind of courting ritual, and in the world of matchmaking, where love—or something like it—is the commodity, things can get weird.Take Fay Goldman, a matchmaker in New York who runs Meaningful Connections. Goldman, who is single, solicited the advice of a client, a successful writer, to discuss a book idea.“I just took the wedding band off,” Carly Spindel said nonchalantly, when we met at a Midtown café on a recent afternoon.“But in business meetings,” she added, having just come from work, “I always wear one.”As a professional matchmaker, Ms.