Dateland: Captain, Dumb Captain


I’m writing this in the cabin of my boat. I’m distracted at the moment because this cabin was the location of the first big makeout session I’ve had since becoming single. Now, I associate the cabin bed with kissing, and I keep looking up from my computer expecting to be kissed, and get quite peeved each time I realize that I’m here alone.

The last time I was single I was 35, and I didn’t have a boat. Now, I’m 50. Do you know what I’ve learned about being single now that I’m older and (allegedly) wiser? Having a boat is a super good idea. It’s like cat nip to the ladies. The minute news of my singlehood hit the wires, I started getting offers from women eager to bring me picnics on the boat. Women who would have never offered me a crust of bread in my bumbling 20s were now preparing me portable feasts comprised of suggestively shaped breads, expensive-looking olives, and all kinds of fancy stuff I’ve never seen in regular grocery stores, all in hopes of going down below with me.  (And, that, thank God, is the extent of my nautical double entendres.)

So, kids, start saving for a boat. It really does work!

Sadly, though, I don’t think I’ve learned anything else about being single.  I’m still the same idiot I was in my 20s.

In the past 15 years, I’ve been in two relationships: one for nine years and the other for six. When my last relationship ended a few months ago, I started making big plans related to my single life.

I was going to date — a lot! I was going to be very European about the whole business. I would go to dinner with a new person each night! Drink expensive wines and never get drunk! Ignore emails for days and then casually respond only when the mood struck! Have serious conversations about art (even though I know virtually nothing about it), and maybe take up smoking just to look French-ish!

This time, I told myself, I’d be very smart about dating. At 50, I have the supreme self-confidence and the sophistication needed to avoid the romantic pitfalls of my stupid youth. I no longer need to play the fool for love. I would be in complete control of my emotions, and I’d merrily move on to the next love interest if a woman gave me the slightest bit of guff.

It was all so good in theory. I couldn’t think of anything that would prevent me from carrying out my plan. After all, I’m devilishly attractive, possess raw animal charm, and, let’s not forget, I’ve got a boat.

But what I didn’t figure into the equation was that while my brain was 100% on board with this sensible plan, and my middle-aged hunger really looked forward to all those lovingly prepared picnic seductions, my heart had other ideas.

Apparently, while the rest of my body has grown more seasoned and smarter, my heart is the exact same nitwit as always.

Which is why, today, I find myself on a cool, rainy day in the cabin of my boat, pathetically reliving the memory of that now week’s old kissing. You see, dear readers, I became smitten with the very first woman I brought aboard the boat. And she didn’t even bring a picnic!

Occasionally, I’m roused from my reverie by the ding of an incoming text. I anxiously reach for my phone, hoping it’s her. Instead, it’s an invitation to the theater from a comely anthropologist or a bit of coquetry from a former crush fishing for a boat ride.  Each time, I drop the phone without responding. Instead, I stare at the cabin ceiling and miserably wait.

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