I have been married and in serious relationships—and I’m old, so I have spent a lot of time being single, too. I have a certain knack for dating special people, and for years folks have said, “You should write a book.” While no doubt this would be a cathartic experience, it also seems like a potential mine field, personally and professionally. So, I will gently dip my toe in, so very gently. I think the statute of limitations has safely run out on this one. 

This memory came flooding back when I read about the untimely passing of Denise Winston, a high-profile matchmaker based in New York. I saw it posted on Facebook, last night. When I was divorced so long ago, I dated like my hair was on fire. Denise was a fancy Upper East Side lady who advertised her services in the back of magazines, like the New Yorker  and New York. I was in my early 30’s (horrors!), and figured I only had a couple of good years left to find a new man. So, off I trotted to meet with Denise in her posh place in the East 60’s. 

I paid her a princely sum (an amount that I will take to my grave) to introduce me to some of New York City’s most eligible bachelors. She did some “consulting” with me (connecting me with her uber-fabulous hair colorist and taking me shopping, for instance). I am paraphrasing a bit, but she said something along the lines, “You need to look less trailer park and more Park Avenue.” Ah, we were off to a good start.

I will tell you about my first introduction. Even now, years later, it  seems odd. She’d given my name and number to a snazzy businessman who lived in the Tri-State area (read: Not New York City). I had been scheduled that weekend to go to Texas for the infant baptism of my oldest friend’s daughter. The snowstorm blew in…and I was stuck in the City. Her date—let’s just call him David—called that evening and we proceeded to have a 2+ hour phone conversation about everything under the sun. He concluded call by saying, “You’ve managed to keep my attention for some time now. That doesn’t happen all that often. I will be in New York next week for a business meeting. How about I send a car for you, and we can go to dinner?” Alright! There was a silver lining with my cancelled Dallas trip. Well, turns out, not so much.

A car arrived at the appointed hour, taking me to retrieve David from a cocktail bar at a Central Park South hotel. We drove on to our dinner location in Midtown West. Somewhere along the way he explained that we would not be dining alone. No, this was a business dinner with 8 or 10 of his associates, also attending the conference. Although I was rather new to the hardcore NYC dating circuit, I thought this a strange and bold move. While we had a nice, interesting phone conversation, could he really know what I’d be like amongst his work colleagues? And, what about getting to know me?  David and I were seated at opposite ends of the table. I was pleased at my ability to chat up strangers about a variety of retail and business topics, not my area of expertise. All seemed amused to hear it was our first “date.” 

David and his car ushered me back to my modest apartment building in East Harlem. He gave me a kiss on the cheek and said, “I will call you so we can set up a proper date.” Days passed with no word. I thought he at least owed me a mulligan as we spent precious little time speaking with each other on our get together.  Finally, after about a week, I called Denise for any intelligence that she’d gathered.  She said those words that will take the wind out of a girl’s sails, “He decided that he wants to date a Jewish girl.” It’s an elegant break-up maneuver because there really is nothing to be said about the assessment. I don’t know if he went on to date Jewish women exclusively, but I feel confident that he knew from the get-go that I was not.

I’m sure that dear Denise made many successful matches, just not one for me. She had a warm and engaging disposition and would call me from time-to-time, just say hello. She even became involved with a charity organization, Hudson Link, where I served on the board. Hudson Link offers college education opportunities for incarcerated men—a far cry from one’s vision of the flaxen-haired matchmaker who lived on the Upper East Side. 

May she rest in peace.

p.s. a bit of follow-up on my date with David. Fast forward a couple of years later, in a plot twist that could only happen to me, I ended up working for the organization that had hosted the conference he attended on that date of ours. We ran into each other at a function for the association. His piercing eyes stared at me, but I could tell he had absolutely no recollection of who I was. To put both of us out of our misery, I re-introduced myself. Ah! Yes! Now he got it. I guess he was embarrassed because he turned to my new boss (I was literally so new that I didn’t have business cards) and said, “Oh, last time I saw Sarah she was standing on the table at a tiki bar singing karaoke.” Of course this was not true—I was stone cold sober making polite chit chat with his business associates about real estate. I know that everything  about the date and that inappropriate and very un-funny  comment was about him—not me. He never could remember my name, in the forthcoming years, although I would regularly see him at conferences and other gatherings. In the end, the connection was disappointing and supremely awkward. And, so it goes.