Dating in Retirement

2001-12-20 15.06.46

Retired, not Over-Tired

I never thought I’d be here, but here I am. And let me tell you – dating at midlife just ain’t what it’s cracked up to be.

What’s that, you say? Internet dating is all the rage! There’s no stigma anymore. It makes perfect sense. With our hypercharged careers, family responsibilities, keeping up with the news and working out – who has the time to meet people anymore? Forget singles bars. What woman in her 50s really enjoys meeting strange men at bars?

Oh, wait. Most Internet “first dates” begin at bars. With strange men. Still, the draw is strong. Everybody seems to know somebody who’s met her significant other online.

“Marie met the love of her life,” said a friend. “She was smart enough to increase her radius of possibilities to 150 miles. And then she found Ben — only three hours away.” Only three hours? What nobody really seems to tell you is that for every online dating success story, there are hundreds of failures: misleading (or outright fraudulent) profiles, years-old photos (at 50, that makes a real difference), awkward conversations, sexual miscues, and clearly incompatible goals.

Dating in Retirement. Pretty scary or pretty fun? How was it for you?

18 years ago I re-entered the dating scene, way before I was thinking of retirement or writing this blog. Divorced after 18 years, I didn’t know happiness was in my future. I just didn’t want to be alone. Heck. After so many years in a bad relationship, I didn’t even know what happiness was.

Then one day I was shopping for some furniture at Price Cutters in North Fort Myers. This was sort of an but in an old bricks and mortar building. And not as nice. Not by a long shot. I didn’t know that I shouldn’t shop there. Neither did my buddy Tim. We were clueless.

Here I was with another loser buddy of mine going though a divorce trying to restock my home with furniture on the cheap after my ex got all the good stuff. Tim and I both bought a bunch of close-out wicker chairs and one sort of retirement rocker (what were we thinking?) and then went to the Athenian Diner across the street for lunch.

The Athenian diner was like dozens of other diners – in New Jersey, except this was Fort Myers, Florida. Woefully out of place.

No matter, we sat down for a Greek salad and some meat loaf and I notice a retired insurance salesman I knew sitting with another couple.

“Hey Gregg! Hows the divorce going?” asks Don.

“Okay,” I reply, “But I’m looking for a tenant for the apartment attached to my house.” Now this attractive brunette that was sitting with the other guy at the booth says, “I’m looking for an apartment, whaddya got?”

After explaining that the house I had was built with a sort of maids quarters with a private entrance, its own living room and access to the pool, Gail lets it be known she is interested in seeing it.

To skip to the Readers Digest version, she decides not to take the apartment after we met at the house the next afternoon, but we start dating soon thereafter, and so ended the shortest post marriage dating run in history. Six months later we were married. I joked after that that I took the apartment, she got the house.

Prior to meeting Gail, however, I made sure I had a date every night. To me it was about not wanting to be alone. Ever the salesman, I was never afraid of rejection, so I asked someone out every night. If I didn’t have a date, it was because I already had a date with a group of people.

I never used the internet dating scene, I just when out and mingled. However, most single people will understand this statement: “I felt alone even when I was with a bunch of people.”

Gail and I have been happily married now for almost 18 years.

What have your experiences been? Any stories to share?


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