Matchmaker Finds the Find, Catches the Catch

Ever heard the expression “all of the good ones are taken”? It’s not true, according to professional matchmaker Leora Hoffman. But the good men, she warns, usually go fast.

“When a good man is back on the market, people look for matches for him left and right,” she said. “The neighbor, the co-worker, the sister – society, for some reason, wants to reach out and match a man, but the same doesn’t happen to women. It’s so unfair.”

Leora said a lot of men get involved with someone new within three to six months after coming back on the market. There are exceptions, of course, including her second husband. He’d been widowed for several years and actively involved with online dating before he and Leora met through mutual friends. “So much of it is timing,” she said. “But I also believe in fate.”

You can read Leora’s Dating While Gray story here. Meantime, let’s look at the business of romance. Everything I knew about matchmaking and matchmakers, I learned from “Fiddler on the Roof.” So when a man I met at a speed-dating event (nice man, no spark, fun time) mentioned he had a friend who was a professional matchmaker, I gave him my email address and asked him to pass it on because I wanted to learn more. You know, for journalism.

Leora graciously agreed to meet and over Happy Hour drinks at the Ritz-Carlton in McLean, Virginia, she talked about Leora Hoffman Associates (LHA), her personal introduction and relationship service for singles in the D.C. metro area. She gave up a career in law 28 years ago to launch it.

“My goal is to find my clients long-term partners, whether I introduce them to two people or 20 people,” she said. “Less is more, as far as I’m concerned, because it’s not about dates. It’s about relationships.”

Most of Leora’s clients are baby boomers. She screens them to make sure they’re a good and safe fit for her network, and meets them to learn their life stories and find out what they’re looking for in a long-term partner.

“Everyone’s had a journey before they come to me,” she said. “I find out what a person’s particular path has been so I can figure out who will be a good partner for them. Some people are looking for the identical type they’re used to. Sometimes I recommend the exact opposite and lo and behold, it works.”

LHA has three membership levels. Clients at the basic level receive referrals to other people in the LHA network for one year, which can be spread over a two-year period. The other two membership levels may include matches outside the LHA network.

“I function like a search firm, really, but for someone’s personal life instead of his or her career,” Leora said. “I’m tied into several networks, and I also have people who give me leads on potential matches.”

Those at the highest LHA membership level receive services including a consultation with an image consultant and a personality assessment by a licensed psychologist.

Gray Dating can be challenging, Leora said, because people who’ve built lives and careers may not be willing to compromise. “Also, people may be very quick to eliminate potential partners without really giving them a chance,” she said. “We’ve been trained to make snap judgments on the job, and that can spill over into our personal lives. People can often be their own worst enemies by making a premature judgment about somebody with very little information. My role is to say ‘Hey, I don’t think you really know this person well enough.’ Or, ‘You’re incorrect about that.’ ”

When Leora evaluates candidates to match, she looks for common values and goals.  She called chemistry “the wildcard. And that’s really in nature. It’s not up to me.”

After she makes referrals, “I like to gauge the probabilities they’ll work out. On one end of the spectrum is pure longshot – and I have played the longshots and have actually been surprised. And on the other end is a really strong feeling about these two. If I have that strong feeling, I’ve never been disappointed. They click like that,” she said, snapping her fingers.

Leora said the matches she makes usually fall in the middle of that scale, but the first two people she ever matched “fell in love in 20 minutes and are still married today.”

For those who don’t experience that instant click, Leora advises going on at least two dates.

“Repeated exposure gives you more information and sometimes, that chemistry doesn’t come out right away, especially if someone’s introverted,” she said. “Everyone’s nervous and anxious at first.”

Leora advises her clients to be patient. “You don’t have to have a conclusion after the first date, after the second date, even the third date,” she said. “You just have to know if you want to spend more time with a person. And that will clear itself one way or the other, eventually.”

Speaking of patience,  Leora says people should trust their own instincts when it comes to sex. However, she believes jumping into bed too soon can derail a potential long-term relationship.  Forget about the so-called three-date rule. Leora thinks a three-month rule may be more prudent.

“Believe me, I had my fun, too, in my single days,” she said. “But I think people should date a few months before they become physically intimate so they know who they’re dealing with. Don’t sleep with someone unless you really think you’re about to embark on an exclusive relationship.”

“What romance really involves, in my experience, is a curiosity. You want to get to know someone, to understand them. There’s something’s drawing you in. The depth is what brings people together. It’s not if they play tennis or if they ski. It’s, you know, do they really ‘get’ each other?  Do they really admire and respect each other?”

“So a good match is where you’re strong in this area, I’m strong in that area; we balance each other, we support each other. We tease each other about those little foibles that each of us has. It’s good-natured, and it’s loving. That’s what a good relationship looks like.”

Gray Daters “are usually more evolved and mature,” Leora said. “You’re not looking for perfection, necessarily. You’re just looking for the right connection.”

For more information about Leora’s matchmaking business, go here.

For Leora’s Gray Dating story, go here.


Dating While Gray: Three Marriage Strikes, But She’s Not Out

Feb. 13, 2017

By Laura Stassi

Francine,* 67,  has played many roles in her life, including stay-at-home mom, schoolteacher, part owner of a family business and now, real estate attorney with her own practice. But 17 years ago after getting divorced for a third time, Francine vowed that the one role she would never play again was wife.

“I just was done” with marriage, Francine said with a laugh. She’s laughing because she is energetic and fun-loving, and laughing comes easily for her. She’s also laughing because in late December, she walked down the aisle for a fourth time.

I interviewed Francine by phone about her Dating While Gray experiences while she took a break from work-related business at a construction site near Nashville, Tennessee. Her vibrant personality sparkled through the telephone connection.

Laura L. Gingerich Photography

The story of how Francine and her fourth husband met seems so happenstance that romantics can only conclude it was meant to be. Francine lived in Nashville; Jack, 58 and twice-divorced, lived in Baton Rouge, Louisiana. They met over the 2013 Fourth of July weekend in Panama City, Florida. Francine owned a condo there; Jack was visiting his Alabama childhood best friend, a retired professor.

Francine and the professor had met through the free online dating site Plenty of Fish. They hadn’t hit it off romantically, but they had become pals and usually got together when they were both in Florida. That holiday weekend, Francine brought her friends to a restaurant for dinner, and the professor brought his. By chance, Francine and Jack sat at the same end of the table.

It wasn’t love at first sight, Francine said. But the men and women wound up spending much of the weekend together after the men’s golf plans got rained out, and by the end of the holiday Francine and Jack were making plans to spend time alone. They rendezvoused in New Orleans three weeks later and “from that point on, we spent practically every weekend together,” Francine said. “This was the most intense thing that I probably ever had experienced.”

By November 2013, they were planning a trip to Europe. “He had never been,” Francine said, “and traveling is a big thing for me. I wanted to see how we traveled together. I have a theory: You need to be on a trip with someone for more than a week, just the two of you, and see how 24 hours a day together is going to work out.”

It worked out. By mid-2014, Jack had sold his Louisiana home, taken early retirement, and moved in with Francine in Nashville. Francine and Jack decided to wed after Francine’s 6-year-old granddaughter innocently said she had overheard her dad telling her teenaged sister that boys and girls don’t sleep in the same bedroom unless they’re married, and that couldn’t be true because Jack slept with Francine in her bedroom, and they weren’t married.

“I realized I was probably not setting a real good example for the grandchildren,” Francine said wryly. She has almost two dozen grandchildren and great-grandchildren.

Jack is about nine years younger than Francine–not a significant age gap compared to the gap with other men she dated after her six-year third marriage ended. “I had lots of relationships,” she said, laughing. “And the men kept getting younger. Pretty quickly, I realized 50-year-old men don’t want 50-year-old women. It doesn’t matter what you look like, or how successful you are, or any qualities that you think might be attractive to someone over 50. They’re not interested.”

Francine met these young professional men through work. After starting her own title and escrow company in April 1999, she networked intensely with real estate agents and mortgage brokers to get business. “I took people out to dinner every night. I took someone to lunch every day. And my social life was kind of built around marketing, and wining and dining customers.”

Her first boyfriend post-third-divorce was a mortgage broker about 15 years her junior who had received an invitation to one of those networking dinners. They dated for nine months. Francine said her four children, all young adults, “were just horrified.”

“But I thought, he’s not married, and I’m not married. What’s wrong with it? And this was really my first time” on the dating scene, “and I was rebellious.”

Francine was a teenager with a baby on the way when she walked down the aisle for the first time with Rich, her high school sweetheart. But he had a college football scholarship, and his parents didn’t approve of the union.

“I was left with a 9-month old, no money,” Francine said. “I had to beg my conservative parents, especially my mother, to come back home to live.”

Francine focused on academics and earned a college degree a semester ahead of schedule, then started teaching. She had been harboring hopes that she and Rich would find their way back to each other. But after he called one night to tell her he had fallen in love with someone else and was getting married, “I rebounded,” Francine said. Husband No. 2, Ronny, was another longtime classmate who also had a brief previous marriage. Francine was 21 when they got married; three children quickly followed, and Francine became a stay-at-home mom.

“Ronny was extremely conservative and very tight-fisted,” Francine said. “We had no debt, but we had no fun either. I guess I wanted more in life than where I was.”

Francine started talking about going to law school, but Ronny wasn’t supportive. They separated after 13 years of marriage; Francine began night classes a month after the divorce was final. She said her kids learned independence and self-sufficiency, but they were starting to act out. Also, money was tight; the family business was in turmoil after the unexpected death of her father.

“I thought maybe if I settled down and had a stable home, it would be beneficial for my kids,” Francine said. So in 1991, three years after graduating from law school, she married husband No. 3, an attorney she had met at a work function. Trey was four years older and had a son from a previous marriage.

Francine said she and Trey had fun when they socialized with friends. But things started going sideways after she changed practice specialties and began staying late at work to overcome a steep learning curve. Trey “wasn’t too happy about that,” Francine said. “He wanted me to get home at a certain time and then sit on the couch beside him while he watched TV and drank.”

“If the kids were home, he was pleasant,” Francine said. “But if not, it was turmoil.” Worried he would become physically violent, Francine moved into a friend’s furnished condo with her youngest child, who was in high school, and got a divorce.

She vowed to never get married again, but that didn’t mean she didn’t want to date.  Francine didn’t intentionally target younger men but when they began showing interest while men her own age weren’t, she didn’t shy away.

“I thought, if I want to date somebody young, I’m doing the same thing that all these guys my age are doing. And if they can get by with it, then why can’t I? What’s wrong with it? I want to play by the same rules.”

Francine did set one rule for herself. Then again, rules are meant to be broken.

“I first said I wouldn’t date anybody younger than my oldest child,” Francine said. But after meeting a man who didn’t fit that description, “I changed it. I said, OK, I won’t date anybody younger than my youngest child.”

Then Francine had dinner one evening with a “cute-as-can-be CPA” she had known for a few years. When she sensed he wanted more than a work relationship, “I said, ‘how old are you, anyway?’ ” Francine recalled, laughing. “He was three months older than my oldest grandchild, so I changed my rule again. I said OK, I won’t date anybody younger than my oldest grandchild.”

Francine has remained friendly with many of her former boyfriends. One even attended her and Jack’s wedding celebration in Cuba over the New Year holiday.


Along with her large extended family, Francine also has a diverse circle of close friends. Seeking to ease Jack’s transition into her well-established and sometimes chaotic life,  Francine turned her guest house into a “man cave” for him. “I was worried he might feel a little overwhelmed in my world,” Francine said, noting that Jack doesn’t have kids. “He’s also a hunter, so he had a lot of deer heads he wanted to hang up.”

But turning the guesthouse over to Jack meant finding new digs for James, Francine’s friend whose “temporary” stay at her house seven years ago has turned into a permanent living arrangement.

“I agreed that Jack could bring his cat if I got to keep James,” Francine said, laughing yet again. So James, who happens to be gay, moved into a bedroom in the main house and now jokes that he, Francine and Jack are a “thruple.” One of Francine’s daughters calls them the modern-day Golden Girls.

“It works out really good the way it is,” Francine said. “We check in with each other every evening about 5 o’clock. Usually, we all three go out to dinner together. We don’t do much cooking.”  The two men enjoy watching Alabama football games together; Francine takes her friend to art openings and other events her husband is happy to skip.

I asked Francine what advice she has for people over 50 who are looking for romance, love and maybe even marriage.  “If you don’t put yourself out there, you’re never going to meet anybody,” Francine said. “And you’ve got to get out of your circle–the same circle that you’ve been in with the same people you’ve been with for years–if you expect to meet anybody else.”

“If you’re sitting at home,” she said, “you’re not going to meet anybody new.”

*Names have been changed.

Have you experienced love and romance, maybe even marriage, at age 50 or older? Share your Dating While Gray experiences by contacting Laura.