Happily Every After

Rebecca Rolfes
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Senior matchmaker

Matchmaker Peggy Wolman’s job is all about hope.


Waiting for the phone to ring, like you may have when you were waiting to be asked to the prom, is not a productive way to find love over the age of 55. It’s easy to default to adolescent pining for Prince (or Princess) Charming if you haven’t been on a date since high school.

And then there’s online dating. For some it’s ideal. For others, the prospect of weed-whacking your way through endless online profiles and the devastation of having your own carefully crafted digital self rejected or, worse, ignored, is terrifying.

But curling up in a ball and deciding that true love only comes once, if at all, is not an option for thousands of seniors who want to share their lives with someone—or simply get out and have some fun. Peggy Wolman, a professional matchmaker and dating coach, loves her job because there is almost invariably a happy ending.

“Meeting mature singles who haven’t given up hope is a powerful moment,” she says. “When a 55-, 60-, 65- or 70-plus-year-old man or woman walks in the door looking for love, it's powerful. Whether never married, divorced or widowed, they are thinking about the next chapter. Whether they find someone or not, their lives will change because they haven’t given up, and because they are ready and willing to make changes. They may not meet ‘the one,’ but they will be in a new place as they emotionally open themselves up to other people.”

Wolman, who recently celebrated her 50th wedding anniversary, has been a matchmaker for seven years following a more than 25-year career as a theater director. “I was ready to pass the baton. I’ve always been a connector and the timing coincided with one of Rachel Greenwald's matchmaking training bootcamps,” she says. “I took her course, and now we enjoy referring clients to each other. She definitely helped me launch my successful career as a matchmaker and as a dating coach."

Wolman also attributes her successful career to her decision three years ago to ask her husband, Dr. Richard Wolman, to work with her. "As a psychologist and member of the faculty of Harvard Medical School, his insights and years of experience are invaluable."

Wolman is diplomatically honest with her clients. She once told a woman—a famous, wealthy, still-beautiful woman—that her age meant finding a match was unlikely. “She was almost 90 so there was little we could do for her,” she says. “And then we met a 91-year-old man.”

Wolman uses a combination of personality testing, interviewing, dating coaching, help with online profiles and personal introductions to match people up or, just as likely, to help them make their own matches.

One of her clients saw a snapshot of a man who looked to be in his 60s hanging behind the receptionist’s desk at her dentist’s office. She commented on the photo and the receptionist explained that it was her father and said, a little tearfully, that her mother had passed away suddenly and she was worried about how lonely her father was.

The receptionist looked up and asked Wolman's client if she would you like to meet her father. "The answer was, of course, ‘yes, and now.’ They’re now happily married. Was that a match I made? No, our client made the match herself, but I helped her learn how to proactively look for love, say who she is and describe the kind of person she needed."

About two-thirds of Wolman’s clients are over 50 and, of those, about half are over 60. They aren’t all looking for the same thing—companionship, marriage, co-habitation, significant friendship, just a date. And the time it can take to get there varies, though there are some commonalities.

Some of her clients need to practice, to meet a lot of people and go on a number of dates. “Sometimes, it’s just getting ready to meet someone,” she says. “Sometimes more mature single men and women are just rusty.”

Some of them need to stop asking questions and start making statements. Men generally talk about their past relationships, hardly a great opener, while women give men the third degree. “When you ask questions,” Wolman says, “that’s your agenda, what you want to talk about. If you ask a man how he likes living in Boston, he will likely say ‘It’s fine.’ That tells you nothing about who he is and may not even be what he thinks. He’s just being polite. We show them how to have a conversation that gets at who they are, not just what they do.” It’s what comes after “because” in a sentence, she explains. “‘I like living in Boston because I’m passionate about American history,’ for instance.”

"Some singles need to be reminded to be truthful about everything, including their age,” she says. “Yes, people online can be dishonest, and, at the same time, we advocate being online to cast the widest net possible. Just as many singles are telling the truth. Those are the ones you want to find.”

Some of Wolman's clients need to let go of finding the “perfect” person. Clients come in with these long lists of who they’re looking for—height, age, education, hobby, income, etc., but according to Wolman, "Love can come in an unexpected package, and when you meet someone you really want to be with, it will have nothing to do with your list.”

When it comes to meeting that someone, Wolman has two pieces of universal advice for all her clients, younger and older.

First, “Get out of the kitchen. Start to have coffee in different places. Get out of your routine. This is especially true as you get older. Different coffee shops, different grocery stores. Draw a new geographical map for yourself.”

Second, “Say hello. You have to practice. Say hello to people as often as you can. It doesn’t have to be a member of the opposite sex. Airports, elevators, wherever you are. Everyone knows a lot of people.” Think of the dentist’s receptionist and her father. “You’re only one degree away from meeting someone special,” Wolman says.

Publication Date: January 12, 2016
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