Dating After 50 on the Main Line

Older doesn’t always mean wiser when it comes to dating. Local experts weigh in on relationship considerations for middle-aged singles.

See also Pepper Schwartz’s “Online Dating 101” advice.

Illustration by Stephano Morri

Blond, blue-eyed and BOTOXed, Linda T. sits at the bar of White Dog Cafe in Wayne. It’s 6:45 p.m. on a Friday, and the place is packed. Sipping a martini and checking her iPhone, Linda darts quick glances around the room. “Just so you know,” she says, “I’m not the kind of woman who goes to a bar by herself and tries to meet men.”

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Except, that’s exactly what she’s doing. Linda explains it this way: “I’m having dinner with friends at Susanna Foo, and I came here first to have a drink. But I do have other plans.”

Those plans are with two married couples. Divorced for three years, Linda has grown accustomed to being the third—or fifth—wheel. She does this “sit at the bar before meeting other people” thing as a way to get herself, however tentatively, into the dating world. “Men want to date younger women,” says Linda, who’s 54. “And there aren’t that many men my age who are single. So really, it’s a numbers game.”

Here are those numbers: In 2010, there were 3,796 marriages and 1,672 divorces in Montgomery County, which has the third highest split-up rate in the state, according to the Pennsylvania Department of Health. By comparison, Delaware County had 2,369 marriages and 201 divorces, and Chester County 2,338 and 1,083. Interestingly, Montgomery County is also the state’s third highest in another statistic: people over the age of 50 getting married.

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Bill Gallen has another number to add to the dating game: 21,040. A 53-year-old sales executive who lives in Media, Gallen joined in November 2010, five months after his 27-year marriage ended. Of his chosen 39-52 age range, had 21,040 profiles within a 20-mile radius.

While Gallen admits that he was thrilled with that number, he quickly realized that a career and kids claim much of the time people in their 20s dedicate to dating. “It took me awhile to find the time to go through all of those profiles,” Gallen says. “Finally, one Saturday morning, I sat at my desk and went through 200 pages of potential matches. Of those, I clicked on 50 profiles. Of those, there were less than a dozen that I’d consider dating.”

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Linda T. sums it up this way. “I used to worry about introducing men to my parents,” she says. “Now, I worry about introducing men to my kids.”

Gallen concurs. “There was a period of … Let’s call it fun,” he says. “There have been relations, but no relationships.”

The truth is, Gallen wasn’t looking for a relationship when he first started dating. He wasn’t emotionally ready.

Most over the age of 50 and single got that way through divorce or the death of a spouse. Before they enter into the dating world, relationship experts say, people have to get over the first marriage.

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“It means a healthy processing of the loss, whether it is a divorce or death,” explains Ruthy Kaiser, a senior therapist at the Council of Relationships and director of the Wynnewood and Bryn Mawr offices. “Divorce brings a variety of trust issues. It doesn’t have to be the result of infidelity—it can be financial. Or it might just be that you trusted your heart and married someone, and now you don’t trust yourself. The question to answer is, ‘Am I ready to trust another person after the failure of this marriage?’ Heal that wound until the answer is ‘yes.’”

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While that may seem like a no-brainer, Kaiser says many people rush into online dating. The hazard is that wounds unhealed will reopen in other relationships—and if the person is 50 or older, there is more at stake. Children, careers and finances can be affected.

The other benefit of healing is healthy self-esteem. “Self-esteem radiates from people, but so does the lack of it,” says JoAnn Ward, co-owner of Master Matchmakers, the Center City-based service. “If you’re giving off the wrong energy, you’ll attract the wrong person.”

With her son Steve, Ward is the author of Crash Course in Love (Pocket Books) and the co-star and executive producer of Tough Love, the VH1 reality dating show that began its fifth season on April 15.

Ward has many Main Line clients, and she insists that dating isn’t any tougher for women over 50. “It’s only harder if you don’t have your act together,” she says. “Is there a lot of competition? Yes. Do men generally want to date younger women? Yes. But more importantly, men want to date women who look good and have great attitudes. You have to be straight in your head, because men over 50—especially successful men—know how to evaluate people. If they think you don’t have your act together, they won’t consider you for a long-term commitment. Men over 50 can see crazy coming, and they know enough to run the other way.”

Self-esteem is important for another reason. “It will help you withstand the rejections that will invariably come,” says Kaiser. “Dating involves disappointment. With a healthy self-concept, it doesn’t need to be experienced as personal rejection.”On the other hand, maybe it is you. Having lots of first dates but no second dates? You may be committing some of the most common mistakes of dating over 50.

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“The No. 1 thing people do wrong on a first date is talk about their ex too much, and too much is anything longer than a few sentences,” says Pepper Schwartz, AARP’s ambassador and relationship expert. “Answer questions about your marital status, how long you’ve been single and how many kids you have—then stop. Say something like, ‘I’ll tell you more about that marriage another time. I want to focus on you.’”

Schwartz is behind, which specializes in the over-50 crowd. Now 65, Schwartz met her boyfriend of six years on a dating website. She’s the author of several books, including Prime: Adventures and Advice on Sex, Love and the Sensual Years. Those sensual years, Schwartz clarifies, begin at 50. “You don’t have to worry about young children or building careers, so you have more time to spend with one another,” she says. “As long as you don’t blow it on the first date.”

Speaking of which: “No sex on the first date,” says Barbara Hefferman, co-owner of Main Line Match. “Rules are rules, no matter how old we are.”

Hefferman has been a local match-maker for 16 years. The first dates she arranges are over dinner, and the men always pay—because that rule hasn’t changed, either. “My top three rules for first dates are: Don’t talk about your ex, don’t have sex, and don’t drink too much,” she says. “If you break the third rule, you’re likely to break the first two.”

Bill Gallen has his own rule. “Don’t lower your standards and settle for someone just because you want to be in a relationship,” he says. “There are good people out there our age, and it’s worth looking to find them.”

See page 5 for Pepper Schwartz’s “Online Dating 101” advice.

Online Dating 101

Pepper Schwartz’s advice for the over-50 crowd.

Lie a Little
“Algorithms break at nine on dating websites.  Fudging your age by a year or two is fine.”

Jump Early
“If you’re looking for a relationship, look at the new men who’ve just joined the website. If there’s a good guy on there, he won’t stay for long.”

Be Specific
“When writing your profile, avoid clichés and generic answers. If I see one more person who says ‘I enjoy walks on the beach,’ I’ll scream.”

Sweat the Photo
“The worst picture is one where the other person has been cut out—that’s just tacky. Go out and get a nice photo. It should look like you on a good day.”

Be Real
“Maybe put in one photo with your kids—but only one, because you’re not looking for someone to parent them. Show who you are; verify your life.”

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