Biggest Surprise with Midlife Dating

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I’ve been interviewed a lot lately to promote the Adventures in Delicious Dating After 40 book series. A question I hadn’t really given a lot of thought to keeps coming up. 

It is, “What’s the biggest negative surprise you’ve had with dating midlife men?” 

Since I keep getting asked this, my response has evolved as I’ve thought about it more. 

My answer? 

Lack of conscientiousness. 

This takes in several behaviors, all, coincidentally, starting with “c!” 

Lack of consideration. I was emailed today, on the day of a dinner date, by a man canceling telling me he’d decided to be exclusive with another woman. It wasn’t his exclusivity that bothered me, but that he didn’t have the consideration to communicate the cancellation via a mode that guaranteed I’d get it. What if I was in appointments all day and didn’t get the email? Calling would have been the preferred method, but I imagine he envisioned a difficult conversation, so took the easiest way out for him. The coward’s way out.

Perhaps since he hasn’t met me, he didn’t feel he needed to treat me with much regard. However, if a man is interested enough in a woman to invite her to a nice dinner, wouldn’t he have enough respect for her to treat her considerately, even if to cancel? My guess is that this is how he treats others, even though he has a senior-level position with a high-ranking politician. So he must know how to earn someone’s respect. But perhaps he’s so talented others overlook his lack of personal consideration. I’ll never know.

Lack of consideration plays out over and over. Are midlife men really so self-absorbed that they have no clue how their lateness, last-minute cancellations, and texting difficult conversations, affect the other person? How disrespectful it feels? Are they missing the thoughtfulness gene? Or were they never taught (or have forgotten) manners? (To be fair, I’d guess there are many midlife women who behave similarly.) Shouldn’t we be able to act like mature adults at this point?

Lack of consciousness of how to make a good impression. Men show up for first dates late without calling, or in wrinkled garb, or take phone calls. Their online profiles are rife with sun glasses- and baseball hat-wearing pictures, often taken from many yards away. How can they possibly think this is appealing and representing them in the best possible way?

Do men really think that on a phone call or coffee date spending 90 percent of the time talking about themselves is attractive? I understand that they are in “impress her” mode, but are they so clueless that they don’t understand that she’ll be way more impressed if he seems to be interested in her life?

Lack of courage. This can be as simple as picking up the phone after a few dates and telling you that you’re not a good fit for each other. Or telling you he’s found someone he thinks is a better match. Or he’s decided to go back to his wife/girlfriend. Whatever the news, have the courage to confront it head on, not hiding behind an IM, text or email. In person is best, but even a phone call is better than electronic communication. I believe men convince themselves it will sting less to receive the missive via text, etc., but it’s really because they don’t want to have to face the perceived difficult conversation. We are adults. We have to have difficult conversations. It’s called “maturity.”

So maybe my real answer is, I’m surprised at some chronologically mature men’s lack of maturity!

I did not intend this to come across as man bashing, as I’m sure we could change the pronoun in every sentence and men would agree that they’ve experienced some midlife women behaving the same way.

So the question to you is, what has negatively surprised you about dating midlife? I don’t want to encourage a rant-fest, but more of a “this surprised me” dialog.

Originally published in Adventures in Delicious Dating After 40


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