"It's like shopping for men; you pick out exactly what you want."

A friend persuaded New Canaanite Brittany Whaley, 22, to join Match.com with this slogan, comparing the online dating service to a clickable Barbie and Ken catalogue.

Whaley consented and joined the singles site looking for choices, but found it contrived.

"It feels a little like you're selling yourself," she said.

Whaley met three Fairfield County men through Match, but most of those dates didn't go so well -- like the double date she said embarrassingly ended with both gents vying for the attentions of the other gal.

Then there was "the nervous wreck" who tried to loosen himself up with a few too many helpings of booze.

"By the end of the night, he couldn't even stand up," Whaley recalls. "I wound up carrying my date home."

While Match has left her looking far from Lady Luck, Whaley said it was a string of equally subpar real-world romantic encounters that originally turned her to cyberspace.

"In New Canaan, it's definitely slim pickings," she said. "Especially for singles in their 20s, there are a lot of familiar faces in town. A lot of the people who are from New Canaan have moved back here because of the job market situation, so it's kind of like a high school reunion. In a way it's kind of nice, but really all it means is that, in terms of dating, we're all back to square one."

Residents and outsiders alike often characterize New Canaan as a bedroom community of middle-aged couples and families. It's a popular perception rooted in fact. Nearly 73 percent of New Canaan men over the age of 15 are married, compared to the national average of about 57 percent, according to United States Census statistics. The same study states that 64 percent of New Canaan females over the age of 15 are married, compared to the national average of about 52 percent. The study also marks the median age of New Canaan residents at about 40, compared to the national average of about 35. For young, unattached New Canaanites looking for romance, the numbers are stacked against them.

"It requires a certain level of confidence and knowing what you want to date here," said New Canaan newcomer Marin Brown. "The men here are either married and 41 [years old] or 41 and single."

Brown, 25, moved to New Canaan from Virginia in 2007. Last year, like Whaley, she joined Match.com.

"You have no idea how many people in New Canaan are on Match.com," she said, adding, "I'll go on a date one night one week and the guy I'm dating two months later, he'll know him."

For many of the born and bred New Canaanites, the dating scene is saturated with contenders too familiar for flirtation.

"In terms of meeting fresh, new faces, it's hard here," said 24-year-old New Canaan High School graduate Tyler Moss. "For a single male, it's hard because a lot of the girls keep to themselves here. It's like they're on a hell-bent mission for shopping and don't have the time to lift their head up even."

New Canaanite Emily Hoffenberg, 23, said she's simply not interested in dating men in town.

"I'm under the perception that I know them all already and there's nothing else here," she said.

According to Hoffenberg, the town lacks a "hot spot" for nightlife and socialization, which she said also contributes to staleness of the local dating scene.

New Canaanite Michael McClure, 23, illustrates the problem with an adage: "There's a joke in New Canaan that when guys from New Canaan go to college, it's always a let-down because the girls are so good looking here. ... So they still are [good looking] and many of them are still here and some are still single. ... The problem is that we all know each other so well and you can't escape your past from the person you were in high school. Everyone pigeon holes one another."

He added, "Proportionally speaking, there aren't a lot of young people or single people [in New Canaan]. ... The concentration isn't high, but there are enough young people to fill Tequila Mockingbird or Gates Restaurant & Bar. In college, if you went to a `Wednesday-night college,' you knew to go out on Wednesday night because that was the big night when everyone went out and you didn't go out on the other nights. The same principle applies here; the only problem is, we don't know when to go where."

McClure believes he has a solution.

Last October, McClure launched a social media initiative aimed at organizing and bolstering the social lives of Connecticut's 20-somethings. Aptly named Connecticut Social, the viral campaign to get young professionals off their couches and onto the bar stools of local taprooms reaches about 370 members through Facebook, Twitter, the blogosphere and good, old-fashioned word-of-mouth.

Still in its infancy, Connecticut Social primarily targets Fairfield County residents, but McClure is working to grow its reach. Connecticut Social sponsors a weekly bar night at Tequila Mockingbird on Thursdays and services its members with online daily drink special listings for an array of bars in New Canaan, Darien, Greenwich, Stamford and Norwalk.

"Our goal is to get 10 percent of our members out to every event," McClure said, adding, "Everyone saying `I never go out because there's nothing to do,' is the reason why there's nothing to do and it's probably the reason why singles aren't meeting new people."

While Connecticut Social isn't a match-making or singles-only service, McClure said many of its members have gone on dates with singles they met at the events. In fact, McClure said he went on a couple of dates with a woman he met at a Tequila Mockingbird event.

Still, speed dating may become a component of Connecticut Social in the future. McClure said a Norwalk-based dating service called Fringles recently approached him to partner on speed-dating events. McClure turned them down.

"While people are still getting to know us, I want to stay away from that," McClure said. "I don't want people to associate us solely with speed dating. Once we get more exposure, we might want to add that to [all the other] events we do."