Dealing with breakups had never been my strong suit. The second I started seeing someone one, I’d start fantasizing about how I’d get out. Things shifted by time I hit my late 20s, when, instead of just imagining my exit strategies, I actually started planning and executing on them.
Of course, this was a defense mechanism — a byproduct of commitment phobia — carefully crafted to protect me from heartbreak. I knew that at the first whiff of smoke, I could simply follow the evacuation instructions that I had practiced over and over in my head, and — poof! — crisis averted.
Compounding this clever exit strategy I'd concocted was the fact that I had an intense fear of settling down (yep, women feel that too). I was convinced that I'd be inviting into my life the kind of vulnerability I'd always dreaded — and that the same partner year after year would eventually stagnate my personality. My solution was to keep one high-heeled boot dangling just outside the door at all times.
Then I was met with a new challenge that arrived in form of a man named Jonathan.
Jonathan was a nice guy, which made me all the more suspicious. Moreover, he wanted the real thing — marriage, commitment, stability, old-fashioned love — which like a spray of DEET, made me want to fly as far away as possible.
Somehow, I resisted the urge to sabotage the whole thing. Before I knew it, we'd been dating for a year. Ever the cynic, I kept searching for a sign that he was a fraud. Could he actually be a moral, loyal guy who was good-looking, in his thirties and single? Was it possible that he loved going to musical theater yet never missed a boxing match? Did he have nothing more than the garden variety of problems that I could handle? Also, could I talk him out of singing in that barbershop quartet?
Even though we had moved in together, my fortress was still up. Whenever things got a little rough, I'd scroll through the old numbers on my phone and think, No matter what, the coke addict guy will take me back, right? Maybe even the puppeteer. Call it pessimistic, paranoid, pathological — or see it as I did: An intelligent approach based on experience. Why set yourself up for a whole new disappointment when you can be disappointed in a way that’s familiar?
Things came to a head in January when we planned a quick vacation to Florida together. Jonathan flew down on Wednesday, and I was to join him that weekend.
I called him the morning of my flight to see if he needed anything. He requested some computer files. I thought, to make things easier, I'd copy over his entire Documents folder to my laptop and bring that down. But his operating system was older than mine, so during the transfer, some files would trigger a pop-up window that I was prompted to 'Accept' or 'Ignore.'
Then it happened: a file popped up called "All Girls I’ve Ever Been With." Keep reading...
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