The Man of A Thousand Dates

Some readers of my story in this week’s Modern Love column might wonder how two people could have a second encounter years apart without recognizing each other. I think we cross paths all the time, and the unusual thing is to realize it.

Rich in 1993

My boyfriend Rich’s first experience of this kind began when he was living in a small Manhattan apartment building where dozens of singles occupied tiny though cozy apartments, with a blizzard of take-out menus over each threshold. He began noticing a cute neighbor, let’s call her Maureen, whose sophisticated sense of style he found intimidating. After a conversation at their letterboxes, he got up the nerve to ask her for coffee. When, on their way home, a rainstorm soaked her expensive suede shoes, Rich was encouraged to hear her sigh, “That’s okay, it was worth it.”

He followed up with a characteristic flirtation, mocking up a fake Chinese menu that, in clever plays on words, invited her to see him again and slipping it under her door. Rich was pleased to have met a woman he liked in real life, and their relationship lasted for a few memorable months. Early on, as they shared their life stories, they found out that they’d gone to the same university. And, comparing notes on who they’d hung out with and dated, it turned out that they’d both participated in a charity fundraiser featuring computer dating—complete with punch cards—and, yes, they’d each gone out on one single such date. With each other!

Back then, Rich’s friends kidded him that he was the man who’d invented speed-dating. The sheer volume of these encounters left plenty of room for coincidence. When he was living in Boston in the 1980s he had a thing for this trance-y, world-music band, or, more specifically its lead singer, an even more angelic version of his boyhood heartthrob, Carolyn Jones (the original goth, Morticia Adams.) “Evangeline” seemed too remote and blissed out on stage to be approachable. Anyway, he was about to move to New York.

About ten years later, in the thick of his serial dating, Rich met a rock photographer, a fascinating woman with cool stories to tell, though they agreed on the spot that they didn’t share chemistry. As they chatted as potential friends, Rich discovered that she’d been documenting Evangeline’s band. When the photographer heard his excitement, she offered to put him in touch with Evangeline, now single and eager to meet someone.

Rich learned that the ex-singer had become a professional astrologer; she kept referring to his zodiac sign throughout the conversation. Because Rich has no patience for any extra-rational topic (we can’t discuss telepathy, the I Ching, or anything spiritual) he decided to not pursue her further. His loss, since not many years later “Evangeline” had made millions on a website monetizing her astrological savvy, while Rich was still penning his personal ads.