The Dating Issue

Baby boomers return to dating

Call them Boomerang Daters. They haven’t played the field in a decade or more. So now they’re figuring out the new rules of romance — or making them up as they go.

C.J. Burton

REMEMBER THE SCENE in Sleepless in Seattle when the widowed Tom Hanks character starts dating again and realizes he needs to learn a whole new vocabulary? “What is tiramisu?” he asks a friend. “You’ll find out,” says his pal, played by Rob Reiner. “Well, what is it?” Hanks asks again. “You’ll see,” Reiner says, leaving Hanks nervous. “Some woman is gonna want me to do it to her and I’m not going to know what it is.”

Oh, for the simplicity of dessert-related jitters. With so-called gray divorce on the rise, according to sociologists at Bowling Green State University in Ohio, a growing number of baby boomers are finding themselves back on the market. They’re decades older, maybe wiser — and definitely facing a changed world. How much trickier have things become since Nora Ephron’s 1993 hit? We’ve got grandmothers worrying about their online profile photos, grandfathers trying to figure out if they should send post-date texts, and both men and women asking the AARP’s love and relationship expert for advice on sexual matters: “These are people who haven’t gone out in 40 years,” says Pepper Schwartz.

And the new tiramisu? That’s “manscaping,” or male grooming below the belt. “Where hair should and shouldn’t be is definitely a huge question,” says Brian Schechter, a cofounder and co-CEO of the dating site.


It’s safe to say that technology’s almost complete infiltration of the dating scene is probably the biggest change. Google Images has essentially eliminated the blind date, and, as Robert Vandor, managing director of the Boston-based LunchDates notes, “even the first date is not a first date. You’ve already seen pictures of their trip to the Bahamas, and you know what they do professionally.”

Suzanne Kreiter/Globe staff
“I feel more comfortable being honest with a woman than when I was in my 30s.” — Rob Clay, 56
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As younger daters can attest, technology brings advantages: You don’t have to hang out at bars, rely on friends for fix-ups, or spend an evening making conversation with someone who’s never heard of Terry Gross (or whoever or whatever it is that interests you). But technology can make daters feel insecure or inadequate — when, exactly, should you respond to a text, and what does “checking in on Foursquare” mean? In many ways, questions like these are merely a symptom of the deeper issue facing boomerang baby boomer daters. Namely, what’s the proper way to behave when you’re engaged in an activity associated with people in their 20s and 30s, but you’ve got kids that age?

“Do you try and do what the kids are doing?” Schechter asks, “or do you say, ‘No I’m just going to be me?’ ” Or, to put it in reality TV terms: Older daters “don’t want to identify with the Kardashians,” Schechter says, “but if they are on a date and the other person does not know who the Kardashians are, it seems like they don’t know what’s going on in this world.”

Of course, it’s not just the culture that’s changed. The daters have, too. They’ve had children, careers, and mortgages, and they’re now looking for someone to fill a different role. “When I was in my 30s, my biological clock was ticking,” says Rita Lombardi, a divorced Canton resident and a manager in the financial services industry. Back then, she signed up for the Post Club matchmaking service, fell in love, got married, and had those children she wanted. She’s now 52 — and back at the Post Club. This time around, a different clock is ticking. “It’s the rest of my life,” she says, “and I want to spend it with fun people. I don’t want to spend it alone.” And where she once felt pressure to hurry up and have children, now she feels pressure to hurry up and set a good example for her children, ages 16 and 18, before they form long-term relationships of their own. “I’d like my kids to see me in a loving relationship,” she says. “I’d like to model that for them.”

Although many women Lombardi’s age complain that men want to date only younger women, Lombardi, who says she put on weight during her divorce, finds one thing is easier in 2012 than it was in 1980. “Before, you may not have known what was on their minds. Now they put it online. Some guys are still looking for Bo Derek.”

Suzanne Kreiter/Globe staff
“I’d like my kids to see me in a loving relationship. I’d like to model that for them.” — Rita Lombardi, 52

Rob Clay says he, too, is a different dater now than when he was younger. The 56-year-old Foxborough resident no longer promises women he’s going to get in touch when he’s not going to. “The first time around, it was ‘I’ll call, I’ll call,’ but I wouldn’t,” says Clay, a general manager at a medical-supply distributor.

“Am I a more compassionate person?” he asks rhetorically. “I don’t think so,” says Clay, who was married for almost two decades and divorced about seven years ago. But he now thinks that honesty is the best policy. “I feel more comfortable being honest with a woman than when I was in my 30s.” Back then, he says, “I wasn’t sure of how I wanted to come across or I wanted to be.”

Even though older daters say they know themselves better than they did when they were twentysomethings, they know the new rules less well. “They hear things and they’re not sure how to act,” says Geoffrey Klein, president of the Newton- based Post Club. For example: “Twenty-five years ago,” he says, “you would have assumed that the guy pays.” But nowadays, the best action is unclear, and “too often both sexes screw it up,” Klein notes. “When a woman offers to share the cost of a meal on a first date, if the guy accepts, she thinks he’s cheap, and if the woman doesn’t offer to share, he thinks the woman is presumptuous.”

And after years of being comfortable with one person — even if it’s someone you end up divorcing — putting yourself out there again is not easy, says Nancy Moore, a senior manager at a local nonprofit who lives in Jamaica Plain. “It brings back all the memories you had when you were in your twenties or your teens. All the game playing that goes on . . . ‘Does he like me? Will you talk to so-and-so and ask him to talk to so-and-so?’ ”

At least, that’s how the 63-year-old felt at first. “Then I said, well, wait a minute, I’m not back at that age. I can create what I want to create.”




IN THE 1930S, Fred Astaire and Ginger Rogers starred in the musical film The Gay Divorcee. Considering new research, perhaps it’s time for a remake: The Gray Divorcee. Although the overall divorce rate in the country remains essentially flat, the rate among those ages 50 and older has doubled since 1990, reports Susan Brown, a sociology professor at Bowling Green State University. She and a colleague found the rate went from 5 divorced persons per 1,000 married persons in 1990 to 10 in 1,000 in 2009.

What’s going on? Brown fingers in part boomers’ more “complex marital biographies.” “They are more likely to be in remarriages that are of short durations,” she explains in an e-mail. “Remarriages are more likely to end in divorce than are first marriages, and the risk of divorce is greatest during the earliest years of marriage.” Other factors include: the rise in the number of working women (many older women are no longer economically dependent on their husbands); changing attitudes about marriage and divorce; and lengthening life expectancies. “Older adults may retire and realize they could live another 20 to 30 years,” notes Brown, “but decide they don’t want to spend that much more time with their spouse.”

Beth Teitell is a lifestyles reporter for the Globe. E-mail her at and follow her on Twitter @bethteitell.