- On September 16, 2017
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By Laura Stassi
Leora Hoffman helps single people find lasting love. But the professional matchmaker was 10 years into her own marriage before finally admitting to herself she needed to end it.
“A matchmaker getting divorced — I thought it would kill my career,” she said.
It didn’t. Leora’s matchmaking business flourished and eventually so did her personal life, even though she decided she wouldn’t date anyone she worked with, nor work with anyone she dated. In 2013, Leora, then in her 50s, married Jim, a widower six years her senior, after they were set up by mutual friends who’d been trying for two years to get them together.
“So much of love is timing,” Leora said. “But I also believe in fate.”
Leora has been in the matchmaking business for almost 30 years. It began when the native New Yorker was a lawyer living with her first husband, also a lawyer, in the D.C. metro area. After their daughter was born, Leora wanted a better work-life balance. So she gave up a demanding litigation position for part-time legal work with a government agency.
“The job didn’t suit my personality,” she said. “But part-time legal work is so rare in Washington that I grabbed it.”
Three years later, on maternity leave with their son, Leora was doing some serious career soul-searching when her sister telephoned. Sis, a psychologist in New York, had been divorced for about a decade and wasn’t having much luck finding love again.
“This may sound crazy,” Sis confided to Leora, “but I’m thinking about going to a matchmaker.” That was Leora’s light bulb moment.
“I knew so many single professionals in the D.C. area who were having trouble meeting people,” Leora said. “And I’ve always had a knack for ‘getting’ people very quickly. I’ve had that energy, that karma, where even strangers felt they could trust me and would confide in me very quickly.”
“So I have really good instincts about people, I’m an extrovert, and I’m a romantic,” Leora said. “Those three elements made me think I’d be a good matchmaker.”
With her husband’s encouragement, Leora met with a start-up consultant, who advised her to do market research before switching careers. Leora returned to the part-time law gig when her maternity leave ended and in her spare time explored the business of matchmaking. She also met with single men and women of all ages and backgrounds to develop a pool of people who would become her core group of clients.
“I love connecting with people,” she said. “To me, talking to a room full of strangers is a joy.”
After a year, she quit the part-time job and launched Leora Hoffman Associates. “The first two people I ever matched fell in love in 20 minutes and are still married today,” she said.
Leora had other matchmaking successes, even as the problems in her own marriage became impossible to ignore.
“I got separated with a lot of trepidation,” she said. “I really did not want to break up my family. He was a wonderful father, but he wasn’t the right partner for me. I felt like I had to be true to my convictions that I’d been sharing with my clients and in workshops and presentations. I had to practice what I was preaching.”
The divorce was contentious and expensive. It dragged out for three years as Leora battled for custody of both children.
“It wasn’t an easy time for me,” she said. “But I found that helping other people meet one another was the best therapy I could have had. Instead of dwelling on my own issues, I just focused on other people.”
“I got great satisfaction from doing it, and my business took off like a rocket,” Leora said. “Maybe people related to me differently. But it was the opposite of what I feared would happen.”
Leora was 39 when her divorce became final. She spent the next decade and a half finding partners for other people while looking for one for herself. “I found it challenging to meet men because I wouldn’t tap into my client pool,” she said. Still, she had a few long-term relationships, including one that almost led to marriage.
“We got engaged and once that happened, he was content to just stay engaged,” Leora said. “He couldn’t move it forward; his commitment issues came to the surface. So one day I turned to him and said, ‘You know what? I’m done. I don’t need to wait. I don’t need to put a gun to anybody’s head. If you’re not willing to make plans to have a life together – and by definition, that’s what getting engaged means – then this is not for me.’ ”
After breaking it off, Leora called her friend “Mary,” a couples therapist. “All right,” Leora told her. “I’m ready to meet Jim.”
Jim, a forensic psychologist and amateur musician, was a friend and work colleague of Mary’s husband. He had become a widower in his late 50s when his wife died after a long illness. For a few years afterward, Jim didn’t even think about dating. But then he decided to throw himself a big party to celebrate his 60th birthday.
“It was his coming out party, so to speak,” Leora said. Jim hired a New Orleans jazz band to supply the music and had asked friends and family from all over the country to join him.
“Oh, you’ve got to meet Jim,” Mary had gushed to Leora after the party. “He’s a classy guy with wonderful friends, and I really see him for you.”
But Leora had been involved with the man she got engaged to, and then Jim ventured into the world of online dating. By the time he and Leora met, Jim hadn’t clicked with anyone. He decided he had been blessed with one great love, and he’d make the most out of being solo for the rest of his life. He agreed to meet with Leora as a favor to his friends, but he wasn’t expecting anything to come of it.
Their first date was supposed to be a quick meet and greet at a bar. They ended up closing the place down. But it wasn’t love at first sight, Leora said.
“He’s tall and very thin, and I was used to shorter, stockier guys. But it was just wow, this is a quality man, and I can really have a conversation with him. It was by far the best conversation I had ever had on a first date.”
“I didn’t know about the chemistry,” she said. “I just thought, let me spend some more time with him and see where, if anywhere, this will go.”
Jim, too, was cautious. Though they began seeing each other regularly, “He didn’t touch me for several weeks,” Leora said. “He did not even take my hand, let alone kiss me.”
Uncharacteristically confused about his intentions, Leora met with Mary and her husband. “I told them I thought Jim was a really great guy, but I wasn’t getting any vibes from him. I didn’t know if he was just looking for a friend, or what. And Mary’s husband said, ‘Leora, trust me. Jim is not just looking for a friend. He wouldn’t be investing this amount of time in you. But don’t try and take the lead here. He’s been through a lot. Be patient.’ ”
“Had I not gotten that piece of feedback, I think I might have blown it,” Leora said. “I’m a strong personality, and I’m not big in the patience department. My tendency would have been to say to Jim, hey, where is this going? But I really liked him, and I understood more about him after that conversation with Mary’s husband. So I just waited and eventually, he made his intentions known. And it just blossomed from there. ”
Leora and Jim dated for about a year and then in a six-month time frame, bought a house together, got engaged, sold their former residences, and planned a wedding.
“Jim told me he wasn’t just looking for a roommate, that he wanted to be married,” Leora said. “I wasn’t exactly needing to be remarried, but I like the idea of marriage. I think it gives you a grounding. It’s the ultimate commitment, and it was something I was very comfortable with doing again with the right guy.”
Are you 50 or older and seeking romance, love, and maybe even marriage? Maybe you’ve found it. Share your story by contacting Laura