boomer dating

A few weeks ago I bought a new car — at least it was new to me. A neighbor was selling his used SUV with very low mileage. I had been thinking it was time to replace my car, but I hadn’t done any research or decided what I wanted. I knew I didn’t want to buy new from a dealer although my last 3 cars were purchased that way. I also knew I wanted a low-mileage car with more cargo space than my sedan, and one that had been well maintained.

This car just sort of fell in my lap. Similar to how many midlife singles want their next mate to show up. They don’t want to do a lot of work to find their next love, but if someone comes along who meets their criteria, they won’t say no.

When a friend recently saw me with the car she asked how I liked it. I thought for a moment, then responded, “I like it but haven’t fallen in love with it yet.”

Boom! It hit me! My car was a lot like some men I’ve dated.

We typically date with a goal: to find someone with mutual attraction. Some of us also want love and a long-term, committed relationship. Some want marriage. Some want just a fling.

After dating a number of people and we don’t have the outcome we want, it can be frustrating. However, if we shift our perspective, we can avoid that frustration — at least most of it. After going out with 114 men and not finding “the one” I’ve learned a positive point of view is healthier than a negative one. It would be easy to say that there are no good men out there. Instead, I see that there are lots of good men, and even the ones who aren’t a romantic fit have other positive attributes.

I’ve noticed a trend. I don’t know if it’s just me or if it is common.

When I’ve met someone online and we’ve exchanged some emails and phone calls, when we meet there’s a sense of familiarity. The meeting seems like a formality, just verifying the other isn’t bizarre looking or socially inept and is attractive to us on some level. Assuming the other person passes for our definition of normal, we agree to a second encounter.

And here’s where it becomes somewhat Twilight-Zone-ish.

When you first meet someone and are deciding whether to see each other again, whether you want to or not, you consciously or unconsciously size each other up. In addition to deciding if you’re attracted to the other, you assess if you are in the same league as the other.

This league can be physical — there have been numerous studies that show people couple with others in the same relative attractiveness levels — with some obvious exceptions. Power and money (although some would say that money is power) is an exception. Thus the hot young woman with the not-so-attractive powerful/rich man. (Could be young, hot man with powerful/rich woman, but we don’t see that quite as much.)

Other elements of this league dynamic — in addition to looks and money/power — could be education, power without wealth (think politician), or fame.

When you decide to date someone you perceive as being a step or two below your league, you’ve found other characteristics that make it OK in your mind. You have lowered your standards in some area(s) because you think he has enough other attributes to mitigate where he doesn’t measure up.

As a generality, men tend to keep relationship details to themselves. Their friends and family may have to probe and prod to even discover they have started dating someone. Guys keep that info to themselves. Only under rare circumstances would they share intimate details with their buddies.

Women, however, tend to be the opposite. It’s common for a woman to tell her gal pals all about the man she’s dating, even sometimes before the woman has even met him in person (if connected online). Once she’s gone out with him, it’s not uncommon for a woman to share all about him, where they went, what they did, what he said, what she found appealing or not so much. If they have a fight, her inner circle is the first to hear. If he makes her happy, same thing.

Most midlife singles have a vision of what they’d like their lives to be like in 5, 10 or 20 years. They imagine adventure trips abroad, luxury cruises, quietly enjoying their homes, or domestic RV trips. They may (or may not) have the resources to enjoy their dreams.

There’s only one thing missing.

Some men just go poof — stopping any communication with you without a word.

Others break up — in person, by phone, via email, or more and more commonly by text. They send a clear message they are moving on.

But there’s another way men exit from a dating relationship.

My friend has been dating a new guy for a month and it was going well. He’s emotionally mature, good looking, financially stable, fun and treats her well. They had two activities planned for the weekend near his home, an hour away from her.

He invited her to stay overnight so she didn’t have to drive back and forth. His guest room was offered as an option so she said yes.

As they hung out the first day, the conversation drifted toward sex. Then he made this disclosure.

At the farmers market, a woman asked the vendor how to tell when the nectarines were sweet and ripe.

“The ones with blemishes and freckles are the sweetest. The prettiest ones aren’t as good.”

I looked at them both and said, “Just like men.”

You’ve been dating a special guy for a while and have had several sexual romps. But you find yourself less than satisfied, even though you’ve giving lots of feedback on what’s working for you when you’re in the act.

Rather than declaring that you’re sexually incompatible, you decide to see if you can discuss adjustments before you get naked together again.

This is not an easy conversation to start, as most people are pretty sensitive about their sexual prowess. No one likes to hear that their special moves aren’t doing it for you, yet if you don’t speak up there’s no chance anything will change.

So how do you broach this sensitive topic?