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

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.”


Single women tell us that while there’s not necessarily a man shortage here, they’re tired of meeting non-committal guys more interested in texting their next prospect than in getting serious.

“It’s not that it’s hard to meet people. I meet nice people almost every day,” explains Cheryl Farley, a personable, forty-year-old in the Stamford real estate business. “But I’m not looking for quantity. I’m looking for quality. The quality is the hard part.”

Lindsey (not her real name), a thirty-five-year-old media executive, says she enjoys living downtown, but adds that the dating scene has lost its allure. “You have to deal with the guys who seem to have forgotten they’re married.”

And some prospects have been so shallow it’s downright discouraging. Single women tell us they’ve been asked—on first dates no less—how much they weigh, what they earn (so gold-digging guys are out there too) and if they packed an overnight bag. “I actually had a guy question-challenge my decision to dip into the bread bowl while we were waiting for dinner. He told me he was surprised by my conspicuous carb consumption,” says Lindsey, who ditched the guy and slipped out the back door with help from the restaurant’s sympathetic staff.

Ava (not her real name), a twenty-four-year-old single with a good job in sales, grew up in Stamford but has recently decided to take an apartment in New York City. “Here, I’m just running into the same people over and over again,” she explains. And she’s increasingly frustrated that a lot of guys her age just aren’t serious. “I was seeing a guy who insists he’s not ready for a relationship but he calls and texts [me] all the time. I just don’t get that.”

Like a lot of the women we talked to, Jillian (not her real name), a smart and witty thirty-one year-old entrepreneur, says the guys she encounters online are a bit more likely to be sincere. She’s pretty much written off her prospects of randomly meeting a guy out and about. “When I meet someone online, I’m excited to show them Stamford and have them see all it has to offer. It’s just not where I want to meet someone.”

Why so adamant it can’t happen here? Well, consider the good-looking guy she met not long ago in a popular Harbor Point restaurant. She agreed to meet him for dinner “against my better judgment” but he spent the whole meal texting with his office about a work project. “And then he had the nerve to say if I wanted a change of scene, his place was really close by,” Jillian reveals, still disgusted.

When he followed up the next day with an e-mail apologizing profusely for his boorish behavior, Jillian reluctantly agreed to a second date. “I was impressed he acknowledged how badly he behaved and I gave him the benefit of the doubt.”

But then came the text messages asking if she wanted to come over “to cuddle” instead of meeting for that second make-up dinner. It got worse. “My friends saw him at the bar hitting on other women at the exact time he was texting me asking me to come and cuddle.”

Deborah Sloan, a former Weston resident and founder of It’s a Date, a consultancy that helps singles craft more compelling online dating profiles, says there’s a good reason why, even in a dynamic environment such as Stamford’s, matchmaking sites can be an effective social outlet. “When you go online, you are engaging with a community of people who are there, more or less, for the exact same reason as you. Not everyone may be sincere, but you just up the odds of meeting a person who actually has the same goals as you.”


Like so many of his peers, Matt Levy found himself venturing online too. “Even though Stamford’s a city now, on the singles scene it can still feel like a small town. I felt like I had to get past Stamford to meet the right person.”

Still, even in the virtual world, Matt found the singles scene was as foreign as the Venus-and-Mars universe he encountered in Stamford’s bars and restaurants. “I think there’s still a lot of confusion out there about how to go about this. If you haven’t dated for any amount of time—say you get divorced or end a long-term relationship—it can be even more complicated.”

Indeed, things seemed so vexing for Matt and some of his single friends that he developed a series of forums he dubbed “The Truth about Dating,” which he conceived not as mixers but as a chance to exchange tips on successfully navigating the online dating and singles scenes. Relying only on social media, he invited singles to join him at Bradford’s Grill & Tavern and got more than twenty-five people at his first event. “I’m by no means a dating guru or expert, but I felt like if I got people together, we could talk and help each other. And the thing that I wasn’t expecting was the variety of people who came. It wasn’t just people my age. I had someone in their seventies, lots and lots of people who were middle-aged who were experiencing dating life again and found it so overwhelming.”

During the seminars he now offers twice a year through the Stamford Board of Education’s Continuing Education program, Matt encourages online daters to expand their geographic reach.mYes, it takes more effort to meet someone from Branford or Brooklyn, but “you have to treat this a bit like a job and you have to put in the effort if you really want to find someone.”

Fortunately, Matt took his own advice. As he got more comfortable dating online, Matt began venturing into New York City for dates. After a few promising online conversations, he made dinner plans with a woman he connected with via the free website Plenty of Fish. They met in a restaurant on Manhattan’s Upper East Side.

Among the things that drew Matt to Alyssa was their “instant chemistry. I loved talking to her and I knew in fifteen minutes—maybe less—that I wanted to see her again.” And much like a happily-ever-after ending, the two fell in love—Alyssa even joined Matt in organizing the dating forums—and were married last July.        

Stamford Agenda

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