Using a Matchmaker to Find Love After 50

Leora Hoffman has been in the business of love since 1989, long before dating apps existed and long before anyone used the word "algorithm" in the context of a first date. She founded Love by Leora after a pivotal moment during maternity leave, when a single introduction she made between two unlikely people ended with them kissing on the steps of the Lincoln Memorial until one in the morning. The next day, she got a phone call: "Forget law. You have found your calling."

Thirty-seven years and countless matches later, she has helped professional singles in the Washington DC area find love in a way that is thoughtful, discreet, and entirely human. She is also the co-author of Catch Me A Catch: Chronicles of a Modern Day Matchmaker, a book that weaves her clients' stories with her own very personal account of finding love after two divorces.

On this episode of Sexy in Your 60s, Leora and I talked about what people get wrong about chemistry, what actually predicts a lasting relationship, and why working with a matchmaker might be the most empowering thing you can do for yourself right now.

From Law to Love: A Career Built on Human Connection

Leora practiced law for the federal government, often in areas like domestic violence and child protection. What drew her to law was the same thing that eventually drew her out of it: a desire to help people in meaningful ways. "What always spoke to me was really to find purpose and meaning in my work," she says.

When she made that first introduction during maternity leave and saw what unfolded, she recognized something in herself. She had a gift for reading people, for seeing possibilities where others saw incompatibility, and for advocating for someone's happiness in the same way a good attorney advocates for a client's best interest. The skills transferred almost entirely.

"It's about listening carefully. It's about having compassion for people who are having challenges and problems. It's about advocating for them in a way where they can really digest the advice and the coaching and the feedback," she says. The profession changed. The purpose did not.

What the Matchmaking Process Actually Looks Like

Leora's intake process begins with a phone call, because she believes conversation reveals things that no form ever could. If there is a fit, she schedules an in-person consultation that typically runs close to two hours. She gathers a complete personal history: family background, relationship history, what has and has not worked, what patterns have emerged, and what a person genuinely needs as opposed to what they think they need.

From there, she functions as a concierge. She arranges the first date herself, rather than simply exchanging phone numbers and hoping for the best. She has learned over the years that momentum matters, and that left to their own devices, people find reasons to stall. She shows photos before any introduction, because she believes in being transparent about what you are walking into. But she also reminds her clients that a photo is a snapshot in time. It does not predict chemistry.

After every date, she collects feedback from both parties. She asks the men not to invite the women for a second date without checking with her first, to give everyone time to think, to process, to be honest about where they are. It is a system built on respect and patience.

The Truth About Chemistry

One of the most useful things Leora shared in our conversation was her breakdown of chemistry into three types: positive (obvious and immediate), negative (inexplicable but real), and neutral (not bells and whistles, but nothing negative either).

Her philosophy on neutral chemistry is worth sitting with. "If you have good communication with that person, if you really have a good time talking to them, if you can really go a little deep with them on the first date and have a meaningful conversation, see them again." Attraction, she says, can emerge. It does not always arrive in the first five minutes.

This is why she recommends meeting someone twice before making a decision. One date is not always enough information.

What Actually Matters in a Partner

Leora helps clients distinguish between non-negotiables and negotiables. Her premise is clear: no one will match a hundred percent in every category. The non-negotiables should be a short list, maybe four or five things, the qualities without which you simply cannot imagine building a life with someone. Attraction matters. Intellectual and emotional compatibility matters. The ability to communicate matters. For some people, a shared spiritual life matters.

What does not belong on that short list: height, where they live, what they do for a living, the color of their eyes. These are negotiables, and Leora has seen more than once how rigidity around them has kept people from meeting someone truly wonderful. She describes clients who came in with lists that covered everything but the kitchen sink, and who eventually found lasting love with someone they never would have considered on paper.

Self-Awareness as the Real Predictor of Success

After nearly four decades in this work, Leora has noticed something consistent in the people who go on to find lasting love. They can articulate what they have learned from past relationships. They can name, honestly, what their own part was in what did not work. They have developed what she calls emotional wisdom.

"The ones who can say, 'I was young, I didn't really understand how to repair relationship problems, how to resolve conflict, and now I'm more wise and more able to do that,' are more likely to be successful in the next situation," she says. It is not about being perfect. It is about being honest.

Barriers Women Over 50 Face (and How to Move Past Them)

The 50-plus demographic is one Leora describes as a privilege to work with. These are people who have spent decades building careers, raising children, and managing their financial lives, often without much time to focus on their own happiness. She encourages them to recognize that this season is, finally, for them.

But there are barriers. Self-limiting beliefs about appearance are common. The woman who says she is not pretty enough anymore. The man who worries about his ability to perform sexually. Leora is direct on this point: "Intimacy is not about how you look necessarily or how you perform necessarily. It's about a loving connection. When people are in a loving connection, those things are far less important."

She also named the fear of what adult children will think. Her response to that is equally direct: "The heart is a very versatile muscle and there can be many, many different forms of love in someone's life, including the love of children and a partner at the same time. They're not mutually exclusive."

It Is Never Too Late

For women in this season of life, the message Leora delivers again and again is one of genuine hope. She has seen love emerge at every age. She told me about a couple in their nineties who both contracted COVID in the early days of the pandemic, before vaccines existed. The woman told Leora later that the love between them was what kept her alive.

Leora also shared her own story with candor: she was divorced twice before finding her current husband in her mid-fifties. When people questioned how a matchmaker could have been divorced twice, her response was simple. She had learned from her mistakes. She was waiting for the right person.

"I've learned that broken hearts do get repaired," she says. "We're not doomed to be alone."

She wants people to stop thinking of matchmaking as a last resort. "Just as you might hire an accountant to do your taxes or a realtor to buy a home, if you are ready for a relationship, this is a gift you give to yourself. An investment that you make in your happiness, not a sign of defeat."

What Sexy Means to Leora Hoffman

When I asked Leora what sexy means to her at this stage of life, she did not hesitate.

"Sexy to me means that you're comfortable in your own skin. That you're in touch with your desires and you're able to act on those desires and not apologize. That you're free of inhibitions that may have held you back earlier in life. That you just live your life unapologetically, and you're just comfortable with yourself."

That is the kind of freedom she is trying to help her clients find, with or without a partner on their arm. And in her experience, the two often arrive together.

If this conversation sparked something in you, I would love for you to hear the full episode. There is so much more we covered that could not fit in this post.

Listen to the Full Episode

Episode 19: Using a Matchmaker to Find Love After 50 with Leora Hoffman

🎧 Listen on the Sexy in Your 60s Podcast Page
🍎 Apple Podcasts
🟢 Spotify
🎵 Amazon Music
▶️ Watch on YouTube

If this episode resonates with you, share it with a woman in your life who needs to hear that this season is not too late for love.

Connect with Leora Hoffman

leorahoffman.com | lovebyleora.com
Catch Me A Catch: Chronicles of a Modern Day Matchmaker — available on Amazon
Disclosure: The book link is an Amazon affiliate link. If you purchase through it, I may earn a small commission at no additional cost to you.

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