The next morning, there were no regrets. “We had a blast,” Madeleine says. Sure, maybe it wasn’t the smartest move to get into a stranger’s car, “but there were three of us, and, I mean, we had our cellphones.”

MADELEINE AND HER TWO FRIENDS had barely pulled up to the bar when one of them began chatting with a cute guy — “in his 30s,” Madeleine remembers. They were on a girls’ weekend at the beach and looking forward to some sun and fun. A few hours and some drinks later, the girls piled into the guy’s car and headed back to their condo. “We are going skinny-dipping!” one of them yelled.


Madeleine and her friends may sound like teenagers on spring break, and indeed that’s what they often feel like. But they met decades ago — they were “ice-skating moms” to daughters on the competitive circuit — and are now in their late 50s, divorced mothers of grown children and having, in many ways, the time of their lives. “You’ll be out at a bar and see some guys you think are cute,” says Madeleine. “Until you realize they’re in their 20s. But you forget! You forget how old you are!” (Madeleine, like other singles in this story, didn’t want to include her full name when talking about her sex life.)

There are nearly 80 million Americans who came of age in the revolutionary free love ’60s and ’70s, when rebelling against your parents’ conservative views of adolescence, premarital sex, and drugs was just something you did. About a third of these erstwhile crazy kids are now single — divorced, widowed, or never married in the first place — and while the drugs and rock ’n’ roll of their past may have stayed there, to hear this group tell it, sex and desire certainly did not. Match.com reports that 50-plus is the site’s fastest-growing demographic. And according to a survey on its sister site for older daters, OurTime.com, 87 percent of 50- to 70-year-old single users say that physical attraction is a “must have” for a potential partner.


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While the Internet has made connecting with others easier, regardless of age, what’s happening also reflects a cultural attitude shift. Nowadays, “there is much more permission to have more than one relationship” in a lifetime, says Cambridge sex therapist Gina Ogden, PhD and author of The Return of Desire. “You no longer see the 55-year-old in a brown cardigan and sensible shoes mourning the fact that he or she would never have a relationship again.” People are experimenting and they’re exploring. Megan Andelloux, founder of the Center for Sexual Pleasure and Health in Pawtucket, Rhode Island, says that many boomers stopping into the center come asking about sexual orientation, like the widower and father of three who “knew he was going to die soon,” Andelloux remembers, “but had always known that he wanted to be with another man.” He wanted to learn how to put on a condom correctly, because he had never been taught. “People tend to realize in their late 40s that they aren’t having the type of sex they want,” Andelloux says, “and so they reach out to the center to make that happen.”

Madeleine, who divorced about a decade ago and lives on the North Shore, says her own father died when her mother was 59. “I always think it’s such a shame,” she says. “She could have had a whole other life.” That said, she adds, “being with a new person after 35 years, talk about scary.”


When Madeleine first started dating her boyfriend, they lived more than an hour’s drive apart. She’d insist on meeting him halfway between her house and his, because she was afraid if he came to her town he’d want to stay over. “But then he did, and we had a nice time, and I thought, What’s he gonna do, drive all the way back [home]?” she recalls. “I was like, you can sleep on the couch. Then I’m looking at him,” she says and grins, “and thinking, Well, that’s stupid. Come on in!”

Of course, there were a few things she wanted to talk about first. She was in her 50s, after all, and had the battle scars, literally, to show for it: two C-sections and a breast reduction. She wanted him to know.

A 54-year-old in Melrose feels a similar impulse before intimate moments. “I’m a breast cancer survivor and I have only one breast,” she says. “When I was younger, I was very comfortable in my skin and becoming sexual was a pretty easy thing for me. Now when I like a person I have to deal with how to share this information so that I feel comfortable and they feel comfortable. And that’s a really strange thing to have to do.”


It’s one reason, this woman says, though she was once married to a man, she has almost exclusively dated women for the last five years. “I have this presumption men are looking for someone with a more complete body,” she says. “Women have expectations, too, but they’re not physical. They want to know you’re independent. That you own your own home and you’re still working.”

Some 25 million baby boomers are single — either divorced, widowed, or never married. Photograph by Dina Rudick/Globe Staff; Photographed at <a href="http://boston.langhamhotels.com/">The Langham, Boston</a>; Models: Kirsten Hede Brierley and Marc Iannaco/Maggie Inc.; makeup: Chantal Ambroise

CHANGING EXPECTATIONS, AND BODIES, are just two of the many complications boomers face in their 21st-century quest for love. Baby boomers — many of whom are also part of the “sandwich generation” — are one of the most stressed-out demographics, mostly still working full time but often called on to care for aging parents and increasingly helping to financially support adult children. Sometimes there’s just no time, or emotional headspace, for romance. “There are things that go on in middle age that take so much energy you don’t always feel you have much to give to dating, or even presenting yourself in an upbeat way,” says the Melrose 54-year-old, who took time off from dating to care for her father and then to mourn his death. For years, she says, it felt like all she could talk about was helping care for him at home and in assisted living.

At the same time, in terms of romantic potential, the parents’ nursing home has become, in many ways, the new corner bar, says Barbara Moscowitz, senior social worker at Massachusetts General Hospital’s Geriatric Medicine Unit. “People often meet each other on the path of caregiving or when there’s an understanding both or one has a major life stress,” she says. This tends to upend the regular expectations of new daters, people who would otherwise prefer to spend every waking moment together. “If someone is busy, it can be harder to spark a relationship,” Moscowitz says. “Harder, but not impossible.”


The rise in 50-plus Match.com users notwithstanding, many boomers seem to prefer meeting potential partners the old-fashioned way. Madeleine had been divorced for five years when she met her boyfriend at a friend’s dinner party. She’d had an online dating profile, but she never got into it. She’d heard too many stories of disappointment. The guys “sound fabulous, then you meet them and you’re like ‘Oh, really? How tall and athletic are you?’ ”

A 57-year-old in Newburyport who’s been divorced nearly three years says she skims Match.com “to see what’s out there” but hasn’t yet worked up the courage to post her own profile. She met the man she’s currently dating when she hired him to do some work on her house, after which he asked her out for pizza. They’ve only had two real dates, though, and she isn’t ready to think about sex.

“It may not sound very romantic, but for midlife daters, finding love is a numbers game,” says Boston matchmaker and dating coach Peggy Wolman, who runs her business with her husband of more than 40 years, Richard. “Online dating can be a challenging concept, but if you look at the number of people who do meet online, it’s wrong to think it’s not one of the smartest options.” The Wolmans spend a lot of time talking to their boomer clients about sex and expectations — how to meet people, what to do on a date, and then some. “A lot of people might not have been intimate with their partner for two, three, four years,” says Wolman. “They’re out of practice and out of touch. Are you kissing on a first date? On a second? What happens when someone invites you back to their apartment?”

Meanwhile, Wolman says, safe sex is a radical concept in a way it’s just not for younger people. One consequence of this: STD rates among boomers are on the rise. Numbers from the Centers for Disease Control and Prevention show that between 2000 and 2010, cases of some STDs, like gonorrhea and chlamydia, nearly tripled among those 50 and older. CDC research has found that one-fifth of all people living with HIV in the United States are older than 55.

“Particularly after menopause, one element that may traditionally keep women more focused on relationship or behaving in a sexually conservative way relative to men — the risk of pregnancy — is gone,” says Carol Queen, PhD and staff sexologist for the sex-toy chain and education center Good Vibrations, which has a location in Brookline. A 2010 Harvard Medical School study, meanwhile, suggested that men older than 50 were six times less likely to use protection than men in their 20s. That women outlive men, adds Queen, “means there are fewer eligible men to go around — and may mean that sexually vital older guys can be players, even if that’s not how they lived their younger lives.”

Boston filmmaker Laurie Kahn produced a series of videos funded by the National Institutes of Health on safer sex for older people, featuring mainly local singles. “One woman talked about going on a weekend trip with a man she was dating, and she suggested they have safe sex,” Kahn says. “He said, ‘No, I won’t do it. It’s not enjoyable for me.’ And he was a doctor!”

Sixty percent of fiftysomethings report having the best sex of their lives. Photograph by Dina Rudick/Globe Staff; Photographed at <a href="http://boston.langhamhotels.com/">The Langham, Boston</a>; Models: Kirsten Hede Brierley and Marc Iannaco/Maggie Inc.; makeup: Chantal Ambroise

METROWESTER MARLA, 53, is mid hot flash as she describes the “best sex ever” she recently had with her ex-husband. They separated seven years ago after Marla found out, through checking his Facebook, that he’d arranged to meet up with his college girlfriend. Afterward, Marla took up with her high school sweetheart, though they’ve since broken up. Marla says she’d be happy to move on to dating new men but has been turned off by the aggressiveness of the guys she’s met through Match.com and JDate, guys who ask for “sexy” photos or dirty talk before they’ve even had a date. “Boomer men like to be very quick and straight to the point,” admits dating coach Thomas Edwards Jr. of The Professional Wingman, who works with men (and women) in Boston and New York. Men “don’t understand the etiquette online, because in so many other ways it’s about instant gratification. That leaves many women jarred.”

That hookup with her ex, Marla says, was a fluke, something that happened after a few too many drinks during a regular get-together to talk about their kids. “I’ve always been the more passionate and forward one,” she says. But for the first time ever, her ex took charge, and she liked that.

In fact, matchmakers say that some clients end up preferring people who are different from their previous partners. “Relationships are a whole different scenario now,” Madeleine says. “It’s not about having kids, bringing them up, feeling the same way about every little thing. It’s much more about yourself.” Whereas her ex-husband was slim and “a very, very stressed-out, uptight person,” her new beau is a burly salesman who sings in the car. He likes to hold her hand in public. “There’s a lot of things where, if it weren’t this time in my life, it wouldn’t work — like, he has no money,” she says. “But I don’t care. Because I have my own money.”

Pepper Schwartz, a Seattle sexologist and the author of Dating After 50 for Dummies, says that boomers aren’t any less ambitious about relationships than they used to be; they just frame them a little differently. “Emotion is still at the forefront,” she says. “No one is looking for someone to compromise with — they’re looking for love and compatibility.” That said, since many men, if given the chance, choose younger women, women have been inspired to look “in different categories,” Schwartz says — career women with blue-collar guys, for example, or interracial and interreligious pairings. This, in turn, can translate to better relationships — and better sex. “Long-term couples often transfer their day-to-day power struggle into the bedroom: demands, expectations, judgment, guilt,” says Kate Feldman. Along with her husband, Joel, they are directors of the Conscious Relationships Institute, and they regularly lead couples in workshops in sex and intimacy at the Kripalu Center for Yoga & Health in Stockbridge. But if those struggles don’t exist — because the kids (with someone else) are grown, the house is paid for — problems in the bedroom start to fade away. As sex therapist Gina Ogden says, “The relationships that don’t do as well are the ones in which a person is looking for someone to fulfill something in their lives, and older people tend to look for that less.”

That’s not to say that the only good boomer sex is new boomer sex. The Feldmans note that in the last few years they’ve seen a huge increase in interest and willingness among fifty- and sixtysomethings to acknowledge that sex in marriage, especially over time, can be a great struggle and that they want to fix what’s broken. “Long-term couples have a challenging road to stay intimate, and there’s even more sensitivity when your body in changing and it’s not what you’re used to,” says Feldman. “Twenty years ago, there was a code of silence around sex. But the baby boomers are more open about talking about it and doing something different.” Wives who’ve come to feel that part of their role was to have sex regularly with their husbands are seeking to have sex (or not) on their terms; men are looking to find ways to remember that pleasing their partners is as important as pleasing themselves.

“One thing we want all senior clients to understand is that sex is something they’re doing because they are the choosers, not the chosen,” says Richard Wolman. “We tell people, rather than thinking about what you want or need, think about what would make you feel good.” Many boomers will eventually pair off, again exchanging the single life for one of monogamy. As Wolman says: “Look, at this age, it’s pretty exhausting to be dating different people all the time.”

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Alyssa Giacobbe is a frequent contributor to the Globe Magazine. Send comments to magazine@globe.com .