How I Finally Lost My Widow Virginity

Our fifth date began at the Museum of Modern Art. John was waiting for me at the entrance. Tall and slim in a charcoal suit, he looked like a Mediterranean version of JFK Jr.

As I wrote in my book, Bottles in the Basement: Surviving an Alcoholic — A Memoir, “We started at the Marina Abramović exhibit featuring live nude models, then stopped to see van Gogh’s Starry Night and John’s beloved Jackson Pollock. He stood in awe of One: Number 31, 1950, a taupe background with an intricate web of dazzling drizzled designs in black, white and gray. It feels like the painting is moving, as if you can sense Pollock flinging and dripping the paint in ecstatic, wavy, squiggly lines. It was the canvas equivalent of my insides, zigzagging with excitement.”

Afterward, at dinner, we ordered raw oysters, juicy steaks and a velvety Shiraz. Later, driving down my block, John said, “I’ll come in for a minute.”

Sitting on my couch listening to Norah Jones and sipping mineral water, we chatted effortlessly, until it was time to stop talking.

“Take me upstairs?” he whispered.

As I also wrote in my book, “My body responded like an orchestra answering the conductor's baton — tap, tap, tap — launching every musician from the jumble of rehearsal's discordant notes into a burst of electrifying harmonious precision.”

At first, the intimacy felt strange, a heady mix of excitement with a touch of panic. But the thrill of anticipation quickly followed. A comfortable yet exhilarating calm washed over me. I was amazed at how easy and normal something old felt with someone new.

The next morning, John sent me a text about the power of oysters. A smile streaked across my face.

But our next date was different, talking about his late wife. Despite my excitement about us, he was still only four months out of them. The next few weeks were quiet, leading up to a Sting concert planned months ago.

I knew this was our last date before it even started. And I wanted him to know I knew. But, after the show, as John drove down my block, he beat me to the goodnight closing conversation that I had planned to initiate.

Months later, John emailed me that his office was relocating and he’d be moving. I replied with heartfelt encouragement.

He responded immediately. “I treasure the time we spent together and even though I guess I wasn’t quite ready, I want to thank you for your love and friendship. You have a special place with me for being there and helping me move on.” 

That was 16 years ago. I would have many more first dates (some second, one multiple) looking for that elusive last first date. There’s no way to get through dating without rejection. You will reject, and you will be rejected.

Most men were nice, just not the right fit. A few were obnoxious. I recall squirming away from the guy who, in the middle of dinner, changed seats from across the table to the banquet seat next to me. Then there was a guy I did not sleep with on our fourth date, but who spent the night, due to the late hour and a long drive home. “I’m going to get coffee and donuts, do you want anything?” he asked me the next morning, as he walked out the door. I never heard from him again.

Then it happened. My first date with Billy was magical. There was instant familiarity, easy conversation, swapping stories, enthusiastic laughter — the hours flew. We agreed to meet for drinks, which segued into dinner and eventually we closed down the restaurant.

At some point — early in the night — Billy asked if he could kiss me. That was 15 years ago, we’ve been together ever since. But I needed to get started. As the iconic Nike ad urges: Just do it.

Have any of you lost a apouse and then started dating again? Let us know in the comments below.