Do you ….?

When a promising first date takes an unexpected turn


Boxes of the canned soft drink Squirt
Photo by author

I recognized him a half block away even though we had never met in real life. The shoulder-length hair, the leather satchel across his back, the black-and-white patterned shirt on his diminutive, yet muscular frame. As he waited for the light, I caught up to him and introduced myself.

We had met “virtually” on OurTime, a dating site for people over fifty. Or as I like to explain to those who’ve never heard of it, the dating app for older folks making a last-ditch effort to find love before devoting whatever energy is left to shopping for Depends.

I’ve come to believe OurTime should be called Just in Time. I was sixty years old and had been on a slew of dating sites since leaving my decades-long marriage. In the past four years I had dated over seventy men, but this was my first suitor through this site. I was exhausted from all the bad dates and dashed expectations. And then a friend, who was unexpectedly successful on OurTime, suggested I sign up… before giving up.

We walked through my Manhattan neighborhood to a wine bar. We chatted about his job as a biology teacher in a Brooklyn charter school — a noble profession in my opinion. It was early September and the school year had just started. He wore glasses as did I. He had a neatly trimmed salt-and- pepper…