Dating after 40

When I’m smitten, or even in the beginning of a budding relationship, I think about the guy a lot.

“I wonder how his day is going. Should I text him?
“I should ask if he wants to come over for dinner Friday.”
“I need to ask him why his marriage broke up.”
“I think I’ll ask him to accompany to the party next weekend.”

This sort of incessant chatter fills my idle thoughts. I rarely have time to think of my other interests.

He was not classically good looking. He had a pronounced nose and craggy face etched from decades of intense work. But his entrancing blue eyes made everything else fade away.

He stood straight so his fit 57-year-old body seemed decades younger. And when he looked at you, it felt like he really saw you. He listened and asked intelligent relevant questions. The combination was sexy — my married gal pals felt it too. He was divorced.

We met speaking at a conference in Singapore. We spent all our downtime together the next 3 days. I invited him to a small dinner party with some of my pals. He got along with them beautifully, balancing listening to their stories, asking questions and sharing his own experiences.

But alas, it was not to be.

Both genders say confidence is one of the most appealing attributes in a sweetie.

However, there is a thin line between confidence and arrogance. Certainty is part of both. Here’s an example of when certainty turned unappealing.

Wooing can be exhilarating, fun, and exciting. It’s nice to be the recipient of a man’s attention and affection. It’s especially nice when he’s good at it, but not so good it seems practiced.

I’ve been the recipient of good woos and not so good ones. The latter wooers seem clumsy, perhaps out of nervousness or lack of confidence. The former seem relaxed; the wooing feels natural, comfortable and sincere. But of course, that could also come from frequent wooing.

I’m on an 11-day cruise. It’s not a singles’ cruise. Am I here looking for love?

One of the unexpected experiences of dating after 40 is when someone you dated dies. I’ve had it happen twice now. Of course, death occurs at all ages. It’s just shocking when it’s someone you have met and become even a little fond of.

We all have stories of some date gone awry because your companion acted strangely. In fact, we love to regale our friends with these stories whenever mid-life dating enters the conversation.

We never see that we might have been the one someone is telling a story about. How could we be the focus of a wacko story? It can’t be true!

But it is.

I spent some time recently with a mid-50s, never-married, long-time friend. He’s been in relationships lasting a few years, but never found someone he wanted to be with long term.

But he does love women and he loves to date. He had 3 dates last weekend with different women. He said he liked all of them but only planned to see one of them again. And he had another set of women lined up for the following week.

I asked why he didn’t just focus on one.

I just returned from 3 weeks in Thailand and Laos. My dating life never seems far from my mind. Here are some examples of a few of the activities that reminded me of my dating life.

Do you ever feel sad at missing expressing a part of who you are? Maybe you love to paint but either don’t have the time or space to do it now. Or maybe you love to swim but you live too far from a pool to do it regularly. Or maybe you are exhilarated by snowboardng but live in Kansas and don’t have the means to get to the slopes.

I was feeling this way when it became clear a new guy wouldn’t evolve into a dating relationship. He said he wanted to take me to dinners, galas and dancing. I thought of my dating wardrobe — flattering evening wear, fun, short skirts with cleavage-peeking tops and other flirty attire. I don’t have a lot of opportunities to wear these clothes since I’ve cut back on dating.