03/22/2013 07:06 am ET Updated May 21, 2013

Finding The Right Question

It was the Fourth of July weekend and, after challenging myself to get out into the dating game again after a 20+ year hiatus, I took the plunge. I met a man for dinner. He said, "Let's meet in your neighborhood." I said that Soho was not a great place to meet because it's so crowded, especially on a holiday weekend. He said, "We'll find a place." So armed with his iPhone and his online Zagat Guide, we set out.

We walked into Dutch on Prince Street, which wasn't crowded at 7:15, but I said, "Trust me, it's going to get packed and noisy." We left and then a few blocks later he said, "I think we should go back to Dutch." Ten minutes later it was packed and noisy and we couldn't get a table.

He made a call. "My friend says we should go to El Cantinori, Union Square Cafe, or Gramercy Tavern."

"All good restaurants, but all probably booked."

He phoned them anyway. I was starting to suspect that he wasn't a very good listener. They were all booked until 10:30. We continue our search and arrive at two places over on Sixth Avenue. We sit down at an outdoor table at the first place, very reputable and popular with those who like to see and be seen. He looks around, checks the Zagat Guide, and decides he doesn't like it. "Why not?" I ask him. "I just don't like the feeling." How about the next one over (also well regarded)? No. We continue on our tour of downtown restaurants and I want to run away, but I'm starving.

We finally settle on Blue Ribbon. He wants to share. So food he'll share, insider knowledge I have about restaurants, not so much.

We eat our dinner, he tells me all about his last relationship. As we're leaving the restaurant his ex-wife calls and tells him about a crisis his daughter is having. I say, "You should go to her! Immediately!" and hail a cab for him.

Actually, "restaurant guy" wasn't my first date of my newly single life. That was with a man who turned out to be married and had lost his son in the World Trade Center on 9/11. We went to his apartment (they had two homes, one in the suburbs and one in the city which allowed for dating) and ordered Chinese food and he showed me a videotape of his son. It was as if we were ordering in pain and loss.

I carefully read online profiles, retooled my own, and spotted a guy who looked great. Over an easy dinner (at the first place we went to!) he seemed intelligent and kind, just as his profile suggested. As he told me about his work, his two homes, his stepson, he seemed perfect. Hope rising. On our second date, another lovely dinner, he volunteered to walk my dog with me. Lucy seemed ok with him -- a good sign, skittish dog that she usually is -- so out into the night we went. Walking down Crosby Street, he told me that his ex-wife had been a professional chef before she went back to school to get a master's in education. Then he mentioned his stepson's name and the town that they had lived in. The names started to register. All the blood drained from my face.

I was on a date with a friend's ex-husband! I couldn't believe it. I was thrown by the fact that he mostly lived in Connecticut -- I couldn't have connected him to anyone I knew so personally. I could never have imagined that our degree of separation was a fairly significant one degree.

The real problem was I knew the backstory of the divorce. I knew he had caused her, continued to cause her, a great deal of grief, both financial and emotional. "I hope this doesn't affect our ability to keep seeing each other," says he. I couldn't get my old dog to run fast enough back upstairs.

I started to think maybe I wasn't really ready for coupling. I went to a grief group at Friends In Deed, a center for people experiencing grief, bereavement, life-threatening illness or caregiving. I had moved into a friend's loft not far from there -- a woman friend who loves dogs -- and even just doing that made me feel less alone. My life was falling apart but also coming together.

I met two men during that time (both about 10 years younger). The first one I met at Friends In Deed. He came there because he had recently lost his brother to non-Hodgkin's lymphoma, and the previous year his father, and also a 10-year relationship. He looked like Grizzly Adams the first time I saw him. He hadn't shaved in months. He cried and talked about his brother and I knew that we would be friends. We became close friends, kind of like Harry to my Sally, but never lovers.

I met another man, this one on He was perfect in a very specific way. His work involved saving the world -- seriously, he was a humanitarian aid worker -- and he was smart and compassionate. I loved listening to him talk about his work and his passion for helping people. But the point is: I could finally get naked, at least physically, with a man. We had fun, sex was relaxed and enjoyable. One night, I read erotica to him and he said, "No one's ever read that kind of thing to me before!" We rarely went out together, on real dates. We just had sex. It was perfect for what it was.

I read somewhere that there are four good questions to ask someone when you first meet. "How is your relationship with your mother?" "What do you do when you're alone?" "What do you do when you're not at work?" "And have you ever had to get through a really difficult time in your life and how did you do it?"

Next guy, I decide to try it.

Me: So have you ever lost anyone, or gone through a difficult period in your life?

Him: No.

Me: Oh. Really?

Him: Never.

Me: No divorce? Lost parents? A close friend?

Him: No.

This isn't my guy. Then another one:

Him: Well, actually, in one year I lost my mother, my father, my best friend, my job and then my wife left me.

Me: Oh... I'm so sorry.

Him: I read books on loss and I started studying meditation. And time helped.

Potential here.

My grief had come in like a semi-truck drove up and just started unloading one horrible crate after another. In the span of just a few months, my 23-year marriage had ended and -- after we told our 21-year-old daughter we were separating -- she decided to move to San Francisco. A few weeks later, after being a caregiver for my mother for the previous seven years, I learned she had bone cancer. My mom had survived over seven years of emergency room visits, numerous hospitals and two hospice stays. It seemed she'd never die -- until suddenly she did.

My job folded. I had to move. I had two dogs, no job, no husband, and no idea what I would do next. No longer a wife, or a daughter, or a worker.

The pain of it all is almost unspeakable. But the truth of it, the fiercely obstinate truth of it is, it's the best thing that could have happened to me.

I know, swell the movie music -- but it's only because losing everything made me work hard and deep to find my most essential self, and what could transform my "just ok, seemed to have enough" life into something that has taught me never to just settle again.

I would not ever settle for a life now that did not include meaning and laughter and eating at restaurants with or without a good Zagat rating. I know that I want love in my life with someone who knows the language of grief and resilience and joy. If that guy who spoke my language hadn't lived 3,000 miles away, I think we might have had a chance.

So I got back out there. I met a man on OK Cupid who was a business consultant and an Argentine tango instructor. Really. He said he was going to a "milonga" -- a tango dance -- on the pier near Christopher Street and would I like to meet him for coffee beforehand? We met for coffee, told each other the Cliff Notes version of our life stories and then went over to the pier. He danced with some of his students and took some time to show me the basic steps. And then he said four amazing words:

"You are a dancer."

The tango instructor, though he doesn't even know it, changed my life. He wasn't a match for me, but I now dance several times a week and I've met a wonderful community of people who love to dance. I wanted to find men to feel close to and I have. I believe that I will find someone to really love again someday, and I understand that though it is harder as you get older, it is not impossible.

I've gotten an advanced degree in the school of hard knocks. I learned what you always hear, that it isn't up to anyone else to make me happy. It isn't up to a man, or my daughter, or my friends -- it's my responsibility alone. I never would have known it, really understood it, if I hadn't lived through these years of struggle. There is happiness, and sadness, and joy, and times of loneliness still -- but also dancing.

Earlier on Huff/Post50:

Where To Meet Singles Over 50