Single in Stamford

Straight talk from the unattached—many using aliases to protect their innocence—covering what's good, bad and ugly in the local dating scene



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Near his thirtieth birthday, Matt Levy ended a long-term relationship. As a newly single guy tentatively testing the dating waters in Stamford, his hometown, Matt found himself immersed in a scene that—for better and for worse—had changed profoundly in the three years since he had last been looking for love. “Parts of it were great,” recalls Matt. “Once you turn thirty, if you’re a decent single guy who’s got it together, you’re in demand.” There was another bonus to being single in this city again, adds Matt; during the years he’d been off the relationship market, Stamford had experienced a seismic social shift.

Just ask Tony (not his real name), a fifty-one-year-old entrepreneur. He’ll tell you that downtown, for several years now, is far from the sleepy suburban scene that he first encountered when he got divorced twenty years ago. “There was a time when Bedford Street rolled up at night—there were literally one or two places you could go—but that has completely changed,” says Tony, who back in the day used to head to the old Art Bar when he was looking for some fun nightlife. “For a while, that pretty much was the scene.”

Now, with hundreds of luxury apartment units and some ninety bars and restaurants—many of them downtown within walking distance, as well as in the revitalized South End and Harbor Point—Stamford has arguably transformed into a singles mecca. “In the summer, there’s almost a street party atmosphere; everyone’s sitting outside, even talking to people at tables at the next restaurant,” says Tony. “I bring clients visiting from places like Boston and they can’t believe the nightlife.”

Matt enjoyed the nightlife too. Yet for all the fun he had experiencing the renaissance—“and for a while, I did have a lot of fun”—when he finally felt ready to put his heart into something more serious, someone was missing in the noisy bar crowds. “I learned that if you are committed to staying single, Stamford is awesome, but it’s a little less awesome if you’re looking to find ‘the one.’”

Matt’s initially elusive efforts to find a soul mate similarly matched the experiences of many of the single-and-looking men and women who shared their stories with us.

Census data suggests that when it comes to finding love, Stamford’s straight guys have the odds-on advantage: The male-to-female ratio delivers ten women for every nine men. And Steve (not his real name), a forty-year-old corporate communications executive who’s been actively dating since ending a long-term relationship not long ago, says he’ll never complain about the romantic possibilities he’s experienced. “I’ve dated everyone from Manhattan corporate lawyers to writers. The good thing here is that there is a wide variety of smart, interesting, dynamic women with a lot to offer.”

Yet unattached guys lament that some Fairfield County single ladies—while statistically plentiful—often seem more invested in whether potential mates earn fat paychecks than in their rich personalities. “It can be frustrating when the first question I get is ‘What do you do?’” says Tony, who adds that while he is professionally successful, “I really want to find someone who’s interested in me.”

Adam Swerdlow, an outgoing twenty-eight-year-old who works in the local financial services industry, says he’s so convinced some Fairfield County women are gold-digging, he sometimes picks up dates in a beat up car (he also owns a nicer one) and takes them to laid-back ethnic restaurants to test their reactions. “If a girl rolls with it and is excited, I know she’s open and not all about superficial things,” he says. “And I love that.”

To be fair to the ladies, Steve says what’s often perceived as “gold-digging” can be blamed on the Gold Coast lifestyle. “A lot of the women here are successful. They are going for MBAs or doing post-graduate work, focused on breaking into management. I find they want a guy who is compassionate, but also can keep up.”

Yet despite his respectable paycheck, Steve says dating in Stamford can be financially draining. “It can cost a small fortune just to meet for appetizers and cocktails,” he says. He tries to limit first dates (he often connects online) to “just coffee” or maybe a walk through a museum.

As for meeting available women, Adam observes there’s something about Stamford’s distinctly suburban underpinnings that makes them seem less open. “I’m a very social guy,” he says. “I can talk to just about anyone, but I’ll approach a woman when I’m out and get the impression what’s going through her head is, ‘He wants to sleep with me,’ when really, I just want to have a nice conversation.”

Steve often has better luck meeting women in New York City. “I see a woman I find attractive in the West Village and I can approach her. Here, I meet someone’s eye at Fairway, she tends to look away. There’s this timidity. Sometimes I still feel like Stamford is a bedroom community, but one where there’s not a lot of action in the bedroom.”

Stamford Agenda

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  • JCC Sara Walker Nursery School Registration

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    Registration for the 2014/15 school Our Nursery School programs are designed to help children learn in an interactive and playful way while...

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    A place to celebrate birthdays and special occasions. Be a guest at your own party! The JCC offers a wonderful space for you and your guests to...

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    2014.09.17

    Are you ready to spend Football Sunday and Mondays with us at the Whale? Join us for $4 Bud Light Drafts, $8 Signature Bloody Mary’s and...

  • College Football Specials

    2014.09.17

    Calling all College Football fans! Watch your favorite college football team score a touchdown at Sign of the Whale. Drink specials include $4...

  • FAll 2014 Semester beginning - Ballet School of Stamford

    2014.09.15

    Our Fall semester begins on September 15th in our beautiful studios at Old Town Hall in Stamford. We offer classes for children age 3 to 18. Our...

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    No school? No problem! Join us for a day of special programs and self-guided activities for all ages. Join SM&NC Educational and Curatorial...

  • Let’s Talk

    2014.09.04

    Thursdays, Sept. 4, Sept. 11, Sept. 18, Oct. 2, Oct. 23, Oct. 30, 1 – 2 p.m. Don’t miss this opportunity to meet new people or...

  • ASTRONOMY NIGHTS: Fall Constellations

    2014.09.26

    Head to the Observatory for a real treat to explore the night sky, planets, stars, and more! Start by enjoying a presentation on the Fall...

  • Neshama Yoga

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  • Endless Summer Saturday, September 27th

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