Lonely In The Hamptons: How To Break Into The Local Dating Scene

Summer in the Hamptons is, quite literally, a hotbed for hookups, relationships and every form of romance in between—romping on the beaches by day, throwing house parties at sunset and bar-hopping by night.

The streets from Westhampton to Montauk are packed with charming bachelors and fiery bachelorettes of all ages, and yet an overwhelming sentiment among local singles is that it’s nearly impossible to find a suitable mate on the East End, where weeklong—or even weekend-long—flings rule.

“Brutal,” they call the dating scene. “Frustrating,” they pout. “Hopeless,” they lament.

Finding “the one” is hard enough on its own, according to matchmaker Janis Spindel, who splits her time between Bridgehampton and Manhattan, without the Hamptons presenting its own set of challenges, for locals, especially. The cost of living is through the roof and affordable housing is nowhere to be seen, often driving young professionals farther up-island, or even out of state.

So when Southampton resident Anita Boyer first met Michael Contino almost four years ago, and found herself smitten, she knew she had to cling on. Or else.

“The real story behind why young and eligible mates are impossible to find is the fact that there is no place for the young and the eligible to live,” the recently engaged Ms. Boyer explained. “Everyone who isn’t kicked out lives with their parents until they are married. I have found myself very, very often to be the only one of my peers living on my own, or with two to three nightmare-inducing housemates. I think that is why it is so hard to pair up, if you aren’t a trust-fund kid.”

Despite the headaches that inevitably come with communal living, it can actually pave the way to finding a mate, Ms. Spindel explained. With new boys come new girls, she said, and vice versa, though the rules of attraction for both straights and gays come from two distinctly different places.

Generally speaking, men fall in love with their eyes, Ms. Spindel said, while women fall in love with their ears. And it can happen anytime, anywhere—so keep an open mind and an open heart, she said.

And, most important, exude confidence without acting desperate.

“If you see someone you might like, start a conversation. They don’t bite. They really don’t,” Ms. Spindel said of single men and women over dinner on Saturday night at Sen in Sag Harbor—which was chock full of available men eating sushi alone, she noted. “It’s very simple. If you are willing and able, and the time is right, and you’re emotionally available, then everywhere you go, you should have your feelers out—for example, even the gym, yoga or spin.”

Suddenly distracted, Ms. Spindel turned to the handsome couple next to her and brazenly observed—as is her fashion—“People have definitely told you that you look alike.”

“Us?” Blake Boshnack stuttered.

“No one ever tells us that,” his date, Kate Zukerman, said.

“That’s kind of scary, actually,” Mr. Boshnack laughed. “She’s my girlfriend, not my sister.”

“They say when you date long enough, you start to look alike,” Ms. Spindel explained to the couple, who instantly relaxed. “And when you’re actually married, you do look alike. How long dating?”

“Five months,” Mr. Boshnack said.

“And where’d you meet?”

The pair looked at each other, smiled, and said together, “Spin.”

Pleased with herself, Ms. Spindel turned back to her meal and said, “See?”

Still, she handed them both her business card—two of the 450 pink mini-pamphlets that she distributes daily—encouraging the couple to pass them along to their friends.

After dinner, she stopped abruptly on her way to the door to give out two more, this time to a pair of gentlemen sitting at the sushi bar. “I am told that you two men are not only good-looking but single, and you’re totally straight,” Ms. Spindel said. “Is that true or false?”

“That is true,” the man to the right responded, smirking at his buddy.

“I’m about to be your new best friend,” Ms. Spindel smiled. “I get people married.”

“Oh, no,” he responded.

“Yes!” his pal to the left, journalist Harry Hurt III, eagerly piped in. “Do you know who this guy is?”

“Should I know who you are?” Ms. Spindel asked.

“No. Where’s your husband?” the mystery man said.

“This is Keith Hernandez!” Mr. Hurt interrupted before she could answer, gesturing to the former Major League Baseball first baseman, who is now broadcasting for the Mets. “He’s Hall-of-Fame material.”

“I’m overrated,” Mr. Hernandez said with a humble smirk, rolling his eyes. “And old. I’m 60.”

“Well, now you really need to let me fix you up,” Ms. Spindel said.

After a few more seconds of playful banter, the matchmaker—who mentored Patti Stanger, better known as “The Millionaire Matchmaker” of Bravo television fame, when she was in the fashion industry—was out the door and on her way to scout at Harlow when she nearly bumped into two blond teenage boys eating ice cream.

“Oh my God, they are so hot. Did you see the two of them? Jesus,” she breathed out. “See, now, if I really was rambunctious, I would have said, ‘I’ll take a lick.’ I can get really feisty. But then I realized that’s Christie Brinkley’s son, Jack Cook. ‘Sure, I’ll lick your cone, Jack. You’re all of 18. Your mother would be thrilled.’”

Inside Harlow at just after 9:30 p.m., the bar scene was hopping with singles, young and old, as Ms. Spindel made her rounds. “When people meet at a bar, they know they’re there to pick up somebody,” she murmured out on the deck, overlooking the harbor. “They have to be socially lubricated. It’s fun, sure, but that’s not necessarily the right way to meet somebody.”

For those on the shyer side, Ms. Spindel highly recommends online dating, at the very least to practice, so that when the right one comes along, it will fall together naturally—in theory.

It wasn’t exactly a cake walk for Sen general manager Jesse Matsuoka when, three years ago, he happened across Jessica Miranda while cashing a check at the Suffolk County National Bank next door. She was the bank teller and, soon after, Mr. Matsuoka found himself at the bank every day, making unnecessary transactions—sometimes $1 deposits—just to find an excuse to talk to her.

“It took me a good couple of weeks to actually get the cojones to ask her out,” he laughed, standing outside the restaurant. “It worked—I was lucky. Out here, it’s very hard for relationships, especially as a local, because the season is just so short. There are a lot of people who come out just for the summer. There’s a lot of people who are into the summer flings, and that’s very big. People are very open with, ‘Hey, I’m just here for the summer. Let’s have some fun, let’s hang out.’ Summer fling, 101.”

But once a bachelor or bachelorette moves off the market, it can be tricky to stay that way, Ms. Spindel said. To a degree, the daters are responsible, she explained, though she deeply believes in fate.

“If it’s meant to be, it’s really in the hands of the universe,” she said. “If you connect with somebody, if you have chemistry with somebody, if you’re intellectually stimulating, if you bring something to the table, it is what it is. If you’re jealous and insecure, that’s not gonna work.

“As long as you keep somebody on their toes and you keep the connection going, and you have trust and respect and laugh, and all the stuff that’s important for a relationship, there shouldn’t be wandering eyes.”

The matchmaker smiled and announced to the bustling sidewalk, “So get out there, ladies and gents! He, or she, won’t wait forever!”