Speed dating on Long Island is making a 'major comeback' post-pandemic: One woman's experience

Most would agree that going on a date with the wrong person constitutes a uniquely cruel form of torture, an evening offering an unwelcome glimpse of eternity. But even a four-minute speed date can drag on occasion, which is why Heather Baron, a 51-year-old speech therapist, keeps a standard question handy, her tried-and-true remedy for awkward silences.

“What are your three must-haves in a woman?” she asks one man, a low-energy music teacher with a bright future on the staring-contest circuit.

“Good teeth, no gaps,” he replies. Heather looks at him. Having detected in the man’s tone a suspicion about her own dentition — one aggravated by the dim-light conditions at Cancun Long Island, a club in Hicksville — Heather makes it known she’s never had a cavity. “Wow, that is spectacular,” he says, belatedly springing to life.

What about his other two must-haves? “No criminal record and four limbs.” Certain he's putting her on, Heather grins and asks how he’d feel about a wooden leg or glass eye. “Can’t do it,” he answers, not grinning back.

“OK, gentlemen, rotate!”

The interruption comes via loudspeaker from Jay Rosensweig, owner of Weekend Dating, which regularly conducts speed dating sessions — first names only, please — at various venues on the Island and beyond. The 20-year-old company has more than 85 marriages and roughly a dozen children to its credit, according to him, and there's been a resurgence of interest in its events with the rise of dating app fatigue. 

Old-school speed dating is making a major comeback on Long Island.

- Jay Rosensweig, owner of Weekend Dating, uses "old-school" as in 1998, the year a Beverly Hills rabbi looking to spice up a Jewish singles event came up with the idea of speed dating.

Heather’s next date doesn't waste any time.

“I’ll tell you a funny story,” he says, taking a seat. The tale is of another singles mixer, one in which he walked up to a woman who’d caught his eye. “She takes one look at me and says, ‘Just so you know, I’m not into Italian guys,’ ” he says. “And I’m like, ‘Neither am I!’ ” It takes Heather a second to realize that this is the sum total of the story’s funniness, by which time she's only able to muster a sympathy chuckle. Undeterred, he adds that the woman at the mixer had laughed loudly and even bought him a shot of Sambuca.

Over the next half-hour, Heather goes on five more dates, one with a Mineolan whose defeated posture matches his must-have — “somebody who’s not crazy” — and another with a 50-ish math teacher from Valley Stream. Things start promisingly with the news that the pair share a mutual love of hummus and the pita chip crackers at Trader Joe’s, but when Heather discloses an affinity for the Lake Grove location owing to its proximity to her home in Port Jefferson, Larry’s sullen reaction suggests a man with a strict policy against long-distance relationships. “You know what? It’s a long island,” he says, tipping his hand.

Right on cue, Rosensweig chimes in again. “OK, it’s halftime. Ten-minute break.”

“I need more alcohol,” Heather says, eyeing the line at the bar. “That was … interesting.”

Still, she will eventually go on a few promising dates too, with wonderful guys who are warm and confident and live not far away in Commack or own their own construction company in Long Beach, or look her straight in the eye and say that honesty is a must-have, or lean in to indicate they share the same love language. “I’m a touch chick,” as Heather puts it.

“For me, it’s not looks so much as the way they carry themselves. Their voice, how they look at me. The whole je ne sais quoi of the situation,” she says.

Rosensweig explains that during three previous speed dating outings, Heather, a divorced mother of three, had attracted a great deal of interest. “But I haven’t found a love match yet,” she reports. Most of the guys who hit on her are either old enough to be her father or young enough to be her kid. “Where are the men in their forties?”

Weekend Dating's speed dating events are keyed to various ages, and Heather had liked her chances at this one, which was limited to men 38 to 52 and women 35 to 49 (plus a two-year grace period she happily took advantage of). About that age-gender discrepancy: Rosensweig maintains it’s a business decision. Eighty percent of the men tell him they want a younger woman, while 50% of the women prefer an older man. 

On this day, 100% of the 13 men and 14 women at Cancun appear ready to fall in love, Heather included. People have told her to be patient, that it will happen when it happens, that the universe has decided the time isn't right, that it’s tough when you’re a walking paradox, i.e., a bundle of “masculine energy” who wants to “step back and let the man take charge.”

Still, she’d found herself nudging the universe anyway, once hiring a matchmaker who set her up with a wealthy CFO. But he took frequent business trips to London and could only see her every six weeks, which was a deal-breaker.

That said, there is one place Heather does not look for love, and that’s the dating apps, something that she, along with most of her fellow speedsters, profess to loathe.

During the day’s anxious preamble, when Cancun’s bar served as a makeshift holding area while Rosensweig waited for stragglers to arrive, complaining about Tinder had been a dependable tension-breaker. Attendees lamented the lack of “good quality people online,” or people who lie, or are married, or whose pictures are old or don’t hint at how shifty-eyed they are in person. 

Once upon a time, speed dating aroused suspicion too. Indeed, when Rosensweig launched Weekend Dating in 2003, the entire concept was taboo. Not anymore. “ ‘Speed dating’ is in the dictionary now. It’s mainstream.” So far this year, he says, business is up 20% from pre-pandemic levels, largely because “app fatigue is 1,000% real.”

For proof that speed dating can lead to true love, Rosensweig has only to point to all the wedding and baby photos on his phone, while a skeptic might well point to Rosensweig himself. The 52-year-old admits that finding The One was a major reason he started his company way back when, and to the shock of just about everybody, he still hasn’t. Is the universe behind that too? “Everybody automatically thinks that I’m married, or if they know that I’m not, I have to be really discreet,” he explains. Occasionally, he sees a woman he’d like to hit on, but if he does and she’s interested, the other men might cry foul, and if she isn’t, “I come off as the creepy guy who owns the company.”

Besides, when he isn’t busy worrying about everyone else finding The One, or collecting $35 or $40 admission fees (plus a two-item minimum at the bar), he’s verifying ages at the door, rolling his eyes at people who claim to have lost their driver's licenses, or rerouting guys who habitually rotate in the wrong direction, or tactfully reminding them that designer sweatpants do not necessarily increase one’s chances at a match, or later, scrutinizing yeas and nays on tally sheets and forwarding contact info in the case of matches. “I’m the shoemaker without shoes.”

By speed dating standards, today’s session will prove a productive one: 11 of 13 men will pick a woman who picks them back, as will 11 of 14 women. Heather will go on more than a dozen dates, a two-hour whirlwind in which she will stump for emotional vulnerability (“that’s a high bar,” one man replied), grieve the loss of her Peloton in a custody battle, hear questions like “do you like nature?” and then hear herself shriek back “I LOVE nature!,” nod gamely at the man who likes women “with the comfortability to make people laugh,” and meet — mercifully — two others she has a good feeling about, men who make her want to know more, men whose names she will circle Yes next to on her tally sheet.

And a few hours after that, Heather will learn that both have circled Yes next to hers too. For a moment it will seem like the universe has reconsidered its decision, although only time will tell.

By Scott Vogel

scott.vogel@newsday.com

Newsday writer and restaurant critic Scott Vogel aims for a refreshing, gimlet-eyed take on the Long Island food scene, often while drinking a refreshing gimlet.