Edit ModuleShow Tags

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

(page 1 of 3)

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.”

Edit ModuleShow Tags Edit ModuleShow Tags

Stamford Agenda

  • "Art Beyond Style" Solo Art Show by Oksana Tanasiv


    September 4, 2015, 5:30-8:00pm Stamford Palace Theater 61 Atlantic St.,  Stamford,  CT  06901   Solo art show by...

  • Sara Walker Nursery School registration is in full swing!


    Community. Caring. Respect. The JCC Sara Walker Nursery School offers preschool programs for children ages 2 to 4 and pre-K, with flexible...

  • Neshama Yoga


    Fridays, Sept. 11 – Dec. 18 (no class on Nov. 27), 9 – 10:30am Neshama Yoga is a fusion of Kundalini Yoga and Jewish spirituality....

  • ReDress-Upcycled Style By Nancy Judd


    September 18 to November 1, Mon.- Sat. 9am-5pm, Sunday 11am – 5pm "Wow! Are you kidding? That can't be made from trash." is...

  • Stamford Museum & Nature Center Facility Use


    January 2 - December 31, After 5pm For a truly unique and memorable venue, host your event or meeting on the picturesque 118-acre former estate...

  • Upright Citizen's Brigade


    Founded by Amy Poehler (SNL, Parks and Recreation), Upright Citizens Brigade Touring Companyperforms a night of provocative sketch comedy and...

  • Team in Training's Rock 'N' Roll Brooklyn Half Marathon


    Brand New Race Coming to Team In Training!   The Leukemia & Lymphoma Society’s (LLS) Connecticut Westchester Hudson Valley Chapter’s...

  • Homemade Pasta Cooking Class - Enriched Pasta


    Our pasta making class series is fun, creative and will turn you in an Italian pasta expert. Under the guidance of Chef Pat Pascarella, you will...

  • Shatterproof Challenge Fairfield County


    Shatterproof, a national organization committed to protecting our children from addiction to alcohol or other drugs and ending the stigma and...



    Ives Concert Park will hold its first annual Harvest Jam this October! Attendees will indulge in great fall themed vendors, delicious local food...

  • Fry Street Quartet at Pequot Library, Saturday, October 10 at 7:30pm


    Prize-winning ensemble that dazzles audiences from Carnegie Hall to Sarajevo makes their only stop in Connecticut this year. Fry Street Quartet...

  • Swimming Activities At The JCC


    Swim School at the J Mondays, Wednesdays or Sundays, September 9 – December 23, 2015 Grades K – 5. Where young children get a...

  • The SM&NC Sunday Farm Market Is Back!


    Sundays, June 28 through October 11, 10am – 2pm Many of the previous vendors are returning and we've added some new vendors to offer a...

  • Market Madness Sundays


    Sundays, September 13 - October 11, 10 am - 3 pm Support local farmers and explore the SM&NC through hands-on activities and with our Market...

  • Daniel Nault; Performing Live at Table 104


    Daniel Nault- Musical Performer Acoustic Singer  Table104  203-388-8898

  • Scarecrow Making


    Sunday, October 4 & 11, 2 - 4 pm October 4:   Session 1: 2 - 3 pm | Session 2: 3 - 4 pm October 11: Session 1: 2 - 3 pm | Session 2: 3 - 4...

  • FALL BREAK OUT DAY: Cycles & Circles


    Celebrate our newest exhibition, ReDress: Upcycled Style by Nancy Judd, and the coming of another fall season, as we explore the cycles of nature....

  • Retired Men’s Club


    Mondays, Sept. 21 – Dec. 28, 10am – 1pm, (No activities or luncheon Sept. 7, Sept. 14, Sept. 28, Oct. 5) Do you enjoy stimulating discussions...

  • Retired Men’s Club


    Mondays, Oct 12 – Dec. 28, 10am – 1pm Do you enjoy stimulating discussions about politics or finance, or just getting together and sharing the...

Show More...
Edit ModuleShow Tags

Most Popular Articles

  1. Summer Scoop
    A night on the town touring Stamford ice cream joints
  2. Mouthwatering
    5 infused waters to make this summer
  3. Hooked on Seafood
    Five places to get fabulous fish in Stamford
  4. August Agenda
    Five things to do in Stamford this August
  5. Child’s Play
    How to Throw The Coolest Kids Birthday Party
Edit Module
Edit ModuleShow Tags