midlife dating

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.

Midlife men have said and done many things that caused me to think, “What??? The examples and my lessons fill Embracing Midlife Men: Insights Into Curious Behaviors. Just when I think I have a handle on what goes on in men’s heads, I’m confronted with a new curiosity.

Good hot cocoa and good sex can both be delicious and satisfying. When each is good, it puts a smile on your face. You feel warm and happy afterwards. You often want more. When shared with someone you care about, they are fun and a great way to spend some time and you don’t say no when either is proposed.

The beginning of getting to know someone is both energizing and frightening. The energy comes from enjoying the conversation and fantasizing about what could be.

The frightening part comes from remembering past first encounters that didn’t result in a second. If you found the man appealing and wanted to see him again but he felt otherwise, the rejection stings.

A friend’s 35-year-old son accompanied his father and step-mother to visit me recently. I’d gotten to know him as a young man and he was in town so they wanted us all to catch up.

He’s a nice guy, but he has some “issues” most women would have a hard time getting around. As he shared that he’s had trouble getting a girlfriend I had to bite my tongue from saying, “I can understand why.”

“Clingy” has different definitions to different people. Some like their space, while others like to be continually touching when together. Others like to show their affection often and in public and some are more reserved.

After a few good phone conversations, we agreed to meet for afternoon coffee. It was a beautiful perfect-weather day, so I decided to wear a cute summer outfit.  I spent an hour taking a shower, dressing and getting my cute on.

Arriving early, I staked out an outdoor table at the coffee shop. He called to say he just drove by and was parking. That was thoughtful.