What It's Really Like To Work With a Matchmaker 

When the New York Times article, "What It's Like to Work With a Matchmaker," appeared in my feed, I nearly dropped my coffee mug. I had just hung up the phone with a San Francisco Bay Area client, where I base my business, now in its 31st year.  

My client, a 79-year-old woman, and I had discussed an upcoming date I set up for her. A man, in his early seventies, had asked her if she would like to meet for a walk through one of my area's favorite scenic routes, and if they felt a spark, an outside sit-down for coffee, perhaps a light lunch.  

Though a bit nervous, my client was excited. It had been a few years since her husband, the love of her life, her partner, her best friend, had died. She missed him, his quirkiness and the way he touched her hair when the sun caught it just right, the way he listened attentively to the poetry she wrote. And the moments she listened to his, and the verses they wrote together.  

We had had many conversations together before I set up that first date. I wanted to learn as much as I could about her, and not just from the detailed questionnaire I require all of my clients to complete.  

I needed to hear her story from her mouth, see the way her lips formed a smile when she reminisced about how her husband burned the toast one morning or how they were late to their daughter's dance recital 40 years earlier. I had to hear for myself why her involvement with a charity she sits on the board on moves her the way it does.  

I can say the same for each of my clients — the 30-year-old free-spirited woman who recently purchased her first home. The late-sixties divorced Silicon Valley techie, author, and art lover who would love to find a partner to share with his love of Eastern philosophy and meditation. And my never-married east coaster who is happiest when on the water and would love a sailing mate.  

We talk. As their matchmaker, as the person who helps convey their life, the dreams they've realized, and the ones they still hope to, to others and on paper through unique story-like dating profiles I write, I help them see their value and the value in those I introduce them to, even if that introduction doesn't develop. We move on, assessing and then taking the rejection, disappointment, or relief they may feel in stride.    

As a matchmaker, I get my clients to contextualize their lives up to the point that we begin working together, so they are in the best possible position to meet the person they seek — a friend, a companion, a lover, or a spouse. As a matchmaker, I put a spotlight on why they haven't had success in the past, on the passages and events in their lives that might still be holding them back. We figure them out. 

And as a matchmaker, one who values the people who come to me, who sees them as individuals and not a mere registration fee, I put potential matchmaking clients on pause if I realize they aren't ready for what they say they are. In doing so, I help them by giving them the time they need, and I help my other clients by giving them access to the strongest possible network of eligible singles who are open to possibilities.  

My circle of clients needs to be filled with individuals who are ready to love — or like. But no amount of promises I make or matches I send to a potential client could ever make them ready. They need to do the work first, which, if they are interested in doing, I can assist them through coaching. I do this by getting them ready to meet new people and date. Yes, dating requires a specific set of skills. People can be taught, and they can learn — from the right teacher. 

The services I offer, which combine online dating with my private network and rest on one-on-one coaching whenever they want or need it (I never turn my phone off to my clients), are what's allowed me to be in this business as long as I have. And why so many of my clients, and the partners and spouses they met through me, are today my friends

As the Times article mentions via the Bay Area dating consultant interviewed, there are many new faces in the matchmaking industry, particularly as the need for them during the pandemic and all the dating challenges that came with the pandemic grew. I have seen this phenomenon as well; Every Tiffany, Dylan, and Hillary is a matchmaker. After all, the shingle they hung and a cool landing page says so.   

But not all matchmakers are the same. The Times article says as much. Just not why.  

After three decades as a matchmaker, this is what I can tell you: A good matchmaker is not defined only by the tangible services their clients pay for; a good matchmaker is defined by the intangible ones they don't — honesty, friendship, and genuine interest.