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7 Surprises About Dating After 50


Think you’ve seen it all in the love and dating department by the time you’re this age? Hardly! Below, some very unexpected twists your fate may take.

By Susan Crandell

on’t get me wrong: Love is amazing at any age. But dating at midlife can in particular give us chills. I didn’t always think this was the case. When I first began interviewing people for my book, Thinking About Tomorrow: Reinventing Yourself at Midlife, I expected to hear of terrible battles and grievous wounds from the dating wars. Instead, I was delighted to find that love is in the air. Men and women are having fun together, savoring romance, discovering true love. Let’s sit in as these happy couples reveal some of the biggest (and most pleasant) surprises that dating at midlife has to offer.

Surprise #1: People are nice—way nice
Remember the Sex and the City episode where Berger breaks up with Carrie on a Post-it note? That would never have happened if they were in their 50s. As my friend Maggie, a veteran of midlife dating, says, “There are no horror stories at this age. People may be
Think back to how you felt about your very first crush. Now, get ready for major déjà vu.
duds, but nobody is mean.” In your 20s and 30s, she says, people would not show for a date, or if it were a blind setup, walk right by if you didn’t measure up to their aesthetic expectations. By the big five-oh, though, the game has changed. People return phone calls; they’re considerate. Maybe we’ve been kicked around enough by life to understand the value of being nice. Whatever the reason, The Golden Rule is writ large for us. Maggie reports, “I’ve done a lot of online and personal ads dating, and I haven’t had a single bad experience. I might think, ‘He’s not The One for me, but he’s The One for somebody.’ She even recalls with fondness a date who said, “We’re not clicking but I have a friend who would really like you.” P.S.: He did.

Surprise #2: You see old friends in new ways
Sarah and Matthew grew up three blocks from each other in a suburb of Atlanta. They were buddies in high school, but then went their separate ways. Sarah moved to New York and launched a career as a news producer; Matthew went to law school. He married, she didn’t, and over the years, they stayed friendly. When they were in their early 50s, his marriage ended. The next time Sarah and Matthew got together — just a casual dinner with an old friend — Cupid sat in. Suddenly they saw each other with new eyes. “I always thought he was a really nice guy, but at the dinner—wham!” Sarah says. Matthew felt it too. Within six months they were living together. The moral of the story: Love can happen anywhere, anytime… and with anyone. And the longer you’re on this earth, the bigger the pool of friends and acquaintances who may suddenly catch your fancy.

Surprise #3: Or sparks may fly with someone you already dated
Judy, an accountant in Des Moines, IA, never married; she never even lived with a guy. She adopted a baby girl from China when she was in her 40s. It was only after becoming a mother that she got the urge to merge. “I adored my daughter but I thought to myself, ‘There’s got to be more,’” she told me. So she started dating—and reconnected with someone she’d met years earlier on a rowing team. “When I met him the first time, I wasn’t thinking about a relationship,” she recalls. “Now, here he was again. I was in a different place. I was looking. We started training together, one thing led to another, and now we’re buying a house.” What Judy learned (and you can,too): Don’t discount people you’ve already dated. Times change, tastes change, and a rematch could be in the stars.

Surprise #4: You can feel puppy love all over again
Think way, way back to how you felt about your very first crush. Giddy? Crazy? Wonderful? The works? Now, get ready for major-league déjà vu. I saw this first-hand
Either I’m with her or she’s on my mind.
when my friends Carol and Joe met. Joe, a doctor in Portland, Oregon, widowed after a long, happy marriage, never imagined he’d fall in love again: “That part of my life was over, I told myself,” he says. But when he met Carol, he was a love-sick teenager. “She’s all I can think about,” he confessed. “Either I’m with her or she’s on my mind.”

Surprise #5: We’re comfortable with our sexuality
Gail Sheehy, author of Sex and the Seasoned Woman, told a story on the Today show recently about speaking before a Richmond, VA women’s club—as she put it, a more conservative group you could not find. Sheehy was a little nervous about the subject of her talk—sex at midlife and beyond. How graphic could she be without offending anyone? But when she arrived, she was greeted this way: “Too bad you got here a little late. We were just having this great conversation about vibrators and orgasms.” The moral of the story: Men and women this age are often beyond having sexual hang-ups and are living it up!

Surprise #6: Nobody sweats the small stuff
“It doesn’t cost you anything to compromise, because your ego is much stronger than it was at twenty,” says Brooks, a 58-year-old psychotherapist in Amarillo, TX. “At 20, every compromise felt like giving up a part of yourself. Now, you just let your date choose the restaurant. It’s no big deal. In a good relationship, there aren’t that many imbalances, and anyway, you’re old enough to say, well, gee, nothing is 100 percent.”

Surprise #7: You don’t have to change each other
We all know the old saw: Marry him now, remodel him later. By midlife, we’ve smartened up. Caroline and Robert, who live in Chicago, married in their 50s. “Dating was a lot less arduous than when I was a kid,” Caroline says. “At 52, you’re a secure person, you’re not struggling with your own identity, there’s no fierce striving at your career. The person you choose—you know he’s not going to change. You’re more accepting.” Robert adds, “The biggest difference in marrying at midlife is having thought it out much better. I have no idea why I married my first wife, other than that she was beautiful.” With Caroline, he shares a passion for travel and books as well, which is a much better recipe for long-term compatibility. And their situation represents exactly the way more and more 50-somethings daters are finding happiness these days.


Susan Crandell is the founding editor of More magazine and author of Thinking About Tomorrow: Reinventing Yourself at Midlife.
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