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Jennifer Schachter (left), Garrett Bernstein (right, with Fabrizia Torazzi) and other singles who are dating again for the first time in years find themselves facing a whole new set of anxieties.
Jennifer Schachter (left), Garrett Bernstein (right, with Fabrizia Torazzi) and other singles who are dating again for the first time in years find themselves facing a whole new set of anxieties. (Globe Staff Photos / Janet Knott)

Just like starting over

After breaking up with a longtime partner, going out is hard to do

Debbie Athy is like any number of Boston-area singles: available, eager, and aware of what she's looking for. Or, rather, who she's looking for.

It's the ''where" and ''how" that are troubling.

When her 3½-year marriage ended, Athy, 34, found herself suddenly solo again and thrust back into the dating game. For four months, the Newtonville resident has been searching for companionship, but her quest isn't progressing as she'd hoped.

''It's not easy being single. It's scary," she says. She adds that the first dating event she attended ''felt like a high school dance."

Scary indeed.

Athy's predicament is a common one these days. Many veterans of long-term relationships who suddenly find themselves single again are plagued by troubling thoughts -- from ''Am I still attractive?" to ''How on earth can I do this? I'm not a kid anymore."

These struggles are even the subject of a new locally produced reality show called ''PossLTR" (which, in the world of personal ads, means ''possible long-term relationship"). Debuting March 26 on WCVB-TV (Channel 5), the show will feature newly single Boston-area locals 35 and up and follow them on the dating scene -- people are invited to audition if, in the words of the show's website, they have ''a compelling story to tell."

Athy says she has encountered many of the difficulties singles face when reentering romance: a lack of confidence, the feeling of being out of practice, an inability to tune into signals people send each other.

''I'm clueless to tell if someone likes me," Athy says. ''You get to the point where [you feel] you're never going to meet people. It's hard to make the first step."

Those who've endured divorces and grueling breakups do march onward. But those first steps can also tread on bruised self-esteems and egos.

''I've spoken to many, many singles about this," says Chris Gonsalves, president of, one of Boston's largest singles clubs, which sponsors dances, dinners, and outings. ''I've heard how nervous [they] were when they walked into one of our singles activities. They also exclaimed their surprise that their butterflies disappear after 15 minutes or so."

Learning to adapt
Dating under any circumstances can be a miasma of anticipatory jitters and fears of getting hurt. But somehow those in their teens and 20s seem better equipped to stomach the emotional roller coaster ride. For singles 30-something and up, dating can be paralyzing. Memories of old lovers and past wounds may still be too fresh.

''For people who are soured after a long-term relationship or a divorce," said Marcia Weiss, cofounder of Collaborative Psychotherapy in Cambridge, ''what they come up with is a seductive belief that comforts them, like 'I tried that relationship thing and it didn't work.' "

Together, Weiss and her partner Carl Schneider teach a class at the Cambridge Center for Adult Education called ''Dating: Beyond the Myths," which uses group exercises and role-playing to address many of the roadblocks associated with previous relationships, such as trust and pessimism. They also try to deconstruct some of the common misconceptions about dating -- such as the one about there being no good men or women out there -- or that dating is a ''fluffy" activity that need not be taken seriously.

David Bryant, 46, says enrolling in the class ''marked the beginning of my active effort at dating -- 'I'm going to work at meeting someone' -- rather than just my passive attitude: 'Gee, it would be nice if I met someone.' "

Bryant, who lives in Cambridge, ended a seven-year relationship in 2000, took a year off to rest and re-evaluate, and has been actively dating for three years. But his first hurdle reminded him just how long he had been complacent about dating. ''It seems simple, but I didn't know how to ask a woman out," he says. Bryant explained the stages of attraction that had befuddled him: initial approach and introduction; first date; getting more intimate; breaking it off if or when things aren't going in the right direction.

For Garrett Bernstein, 38, of Medford, being aware of the various playing fields was crucial to getting reacquainted with the single life after his divorce. ''The singles scene [is] designed for the one-night hookup," says Bernstein, a self-described ''on-and-off-again dater since 30" who is now with a woman named Fabrizia Torazzi. ''The music will be loud enough to prevent you from having a meaningful conversation, but the drinks will be strong enough to make you think that you did. Make sure to lie about your age, income, and last name."

''The dating scene, of course, is quite the opposite," Bernstein says. ''Be sure not to sleep around in the dating scene -- it is considered dishonest, and you'll be labeled with fear of commitment by the very people you'd want to date."

Another concern is the ''I'm a time traveler from another epoch" fear.

''Back then, we didn't have those dating services that purport to extract your DNA and come up with your one true love," Bernstein quips. True, online dating can seem intimidating to older singles. But once they take the plunge, it actually helps them try out their new selves and practice e-flirting in a relatively risk-free environment.

''I had some trepidation about having been off the market for 15 years," says Elise MacDonald, 38, who lived in Boston and Newton in the early '90s and now lives in New Ipswich, N.H. ''Fortunately this concern was quite unfounded. I actually adapted to the techniques pretty quickly."

''I really do think the online thing is the way to go," says MacDonald, who finds cyberspace a relief from the nightclub scene, which favors appearance over substance. Now she's with a guy she met on ''You get to know the person sort of from the inside out. You get to hear about their interests, including an idea of their thought process and writing style, a real plus, in my opinion. Then, when or if you decide to meet, the exterior and physical nature of the person is the last piece of the puzzle."

Doubt vs. maturity
Huey Lewis & the News may no longer be blasting in the sports bar, but other than that, the basics of dating really haven't changed since the Reagan administration. Men and women still gather at social events and exchange numbers, or are introduced by mutual friends. Older daters often find it's not the dating world that has changed but rather that they have changed.

''What is dramatically different for me from being single in my 20s compared to my 30s is internal," says Jennifer Schachter, 35, of Arlington, who began dating in late 2003 after the end of an eight-year relationship, five years of it married. ''I can remember feeling lonely in my 20s and thinking I needed someone -- in the famous words -- to 'complete me.' But now the thought of feeling that way seems so foreign and absurd."

Sure, the newly single may feel temporarily inadequate, if not burdened with piles of emotional baggage. But for many contemplating another significant relationship, this load is outweighed by experience, maturity, and hopefully greater self-awareness than at any other stage of their lives.

In the words of Elise MacDonald, ''36 was a long way from 20." She realized she had a better sense of who she had become, which served her well when returning to dating.

There is, however, one final pressure: to not make the same mistake again in finding a mate.

''I didn't do a good job of dating in my early years, and it showed," David Bryant says. ''[I went] for Ms. Right Now, rather than working to find Ms. Right. This time around, I've thought a lot more about my dating process, and what it is that I'm looking for in a partner."

Now that Bryant considers himself an experienced single, the pitfalls and trepidations of dating no longer overwhelm him.

''Success can be achieved," he says. ''In the last couple of weeks I've met someone that I'm really enthusiastic about, and who's really enthusiastic about me."

Results are simply a matter of getting ''out there" again. Debbie Athy remains hopeful. Dating is just like other skills, she says. It takes work and improves with practice.

''The more you do it," Athy says, ''the easier it gets."

Ethan Gilsdorf can be reached at