10 Tips for Successful Dating Over 40

You’ve been single for a while. You would like to have a special man in your life. But how?

Women reentering the dating scene after a long absence need to first examine if they are ready to date again. After all, not only is there the possibility of being swept off your feet by a romantic, loving man, there’s the chance of being swept over the cliff of heartbreak. Here are some tips on how to ensure you enjoy your adventure of dating after 50, not dread the next coffee date.

When your ex dies

My ex learned he had cancer 2 years ago. Since we didn’t keep in touch, I learned of it a year ago. He did semi-weekly podcasts for a few dozen friends to update them on his health. I listened to the previous 100 podcasts before reaching out via email.

He said he was thrilled to hear from me and was stunned that I would listen to all 100 previous podcasts. I’d asked if now we could be friends and he said he’d like nothing better. We exchanged a few emails and he said he’d like to talk about the end of our marriage as he was sure I had some questions — which I did. I asked for some good times to call since he was so overwhelmed with treatment appointments and recovery. However, he never closed the loop to set up a call, so I decided I’d make the 600 mile trip to visit him and have that discussion face to face. A few months ago, his doctors had given him 18 to 24 months, so there was plenty of time.

How much mind space does he take?

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.

Right man; wrong continent

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.

The woo dance

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.

Can you be wacko on dates?

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.

Dating as sport

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.