“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.
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.
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.
“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.
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.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 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.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.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.“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. They are going for MBAs or doing post-graduate work, focused on breaking into management.