My exit strategy

I was desperate to leave my single days behind. Could I do it if I put my mind to it?

By Steve Calechman
June 20, 2010

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If there’s one thing that I’ve learned from my dating career – aside from the fact that everyone apparently loves hiking – it’s that being 41 and single is not what the ladies would technically classify as sexy. That was my status last year, and if we’re being honest, it was starting to wear on my confidence. I clung to the idea that I was still a decent catch, but I knew the unavoidable reality was that I was a little past fresh.

It didn’t stop me from trying. I updated my online photos and looked for women within 30 miles of my ZIP code. I let people play matchmaker. I tried eight-minute dates, seven-minute dates, three-minute dates. And if you think that three minutes isn’t enough, you’re mistaken: With the wrong person, three minutes can be a slow-grinding, one-word-answer eternity.

I was tired of the near and complete misses. Something had to change, and last April I was presented with the opportunity.

I made my daily online visit and kept going back to the profile of a woman who said that she liked 30 Rock and probably spent too much time with her dogs. I don’t remember what I wrote, but I received a quick reply, a phone number, and some unpublished information. While she had posted in Boston, she was living in Chicago with vague plans to move here in the fall. Oh, and she was working in Tennessee.


Starting something with this woman made absolutely no sense. I’d done long-distance relationships and wasn’t a fan of the usual dynamic: hope, elation, followed quickly by a hatred of the Triborough Bridge. Then I remembered how I’d told a friend that I didn’t write any woman’s number in my address book because it would doom the relationship, and he’d asked: “How’s that been working out for you?” An excellent point. Shaking things up with a call down South wouldn’t be the worst thing.

Jenny and I had a solid first conversation. She mentioned getting together when she visited her mom here in July, which sounded fine to me. But that meant more than three months to kill, so I called the next week and the following one and decided that waiting until the summer wasn’t going to happen.

I crafted some excuse to be in Chicago and asked her out to lunch on May 15. Amazingly, she did not find the idea entirely moronic.

We shared a pizza, had dinner the next night, and met for breakfast on Sunday morning. She took me to the airport and left me excited and completely terrified that her feelings would fade upon my departure. They didn’t, and we continued with our unconventional courting, since she was still in Chicago and traveling for work on six-week stints. It still made absolutely no sense.

And yet, in a way, it all made perfect sense.

What followed were weekend get-togethers around the country and a new kind of education. I learned the nuances of Yelp reviews. I learned that trying out a GPS for the first time in a strange city is not ideal. And I learned more about Nashville hotels than I ever expected. (I recommend the Doubletree. The Starbucks in the lobby saves lives if someone is without caffeine after 10 a.m.)

We also had to talk a lot by phone, and while we ended up discovering bedrock similarities, like a respect for oatmeal and an aversion to Facebook updates, what I really learned is that the girl doesn’t flinch from any subject. Nothing is held onto, and nothing lingers. She’ll talk. She’ll listen. And she always wants a solution over a battle.

Jenny eventually did move here, and we quickly learned that we got along just fine in the same time zone, and soon I definitely knew what I kind of already knew. I asked. She said yes, and I got my one true wish: to never have to go on another first date again. Now we’re trying to decide between a band and a disc jockey and whether the world really needs another plated salmon dinner. These aren’t bad problems to have.

Part of me wishes that we’d met 10 years ago, only so we’d have 10 more years together. But then I remember that while I had my moments, I was kind of useless 10 years ago, and I wonder if I would have truly been ready for her. Mostly, I’m just thankful. I can’t imagine going forward without her. I’m glad that I won’t have to.

Steve Calechman is a freelance writer and comic in Waltham. Send comments to Story ideas Send yours to Please note: We do not respond to ideas we will not pursue.

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