Someone once misquoted Albert Einstein as defining insanity as “doing the same thing over and over again and expecting different results.”

The same could be true about dating in New York.

There was a point last November where I was going on first dates four or five nights a week. I remembered every little detail about each man—that was never the problem, though often I would repeat stories. The Writer had dropped out of college, moved to New York at 19 and developed a crippling self esteem issue that would only be resolved behind closed doors with his therapist and a heavy dose of antidepressants. The Salesman took his clients out drinking on Thursdays and followed up all alcoholic activities with a journey to a strip club fueled by Jack and cokes and bathroom coke. The Lawyer pretended he was 27, and it wasn’t until he admitted his real age (38) did his two-bedroom palace on Park Avenue with working fireplace,
antique furniture and extensive Italian wine collection finally make sense to me, though I still maintain his diminishing hairline could have fooled anyone.

“I love being single!” I told my friends, home from another failed date and nursing a good three fingers of Dewars in a plastic tumbler. “I don’t want to be in a relationship at this point in my life.”

Most of them believed me, or else skeptically agreed with my stance on the matter. My Jewish mother was a different story. “What do you mean ‘at this point’ in your life? You’re practically 30 and you’ve been single for four years! When will you be ready for a relationship, when you’re 45?”

“I am 25 and nowhere near 30. And it has nothing to do with being ready…it has to do with my freedom,” I insisted. “I love being single because I get to make my own decisions and be my own person. Plus, I get to meet more people than I would if I was tied down in some boring relationship.”

I was only partly correct. I loved being single because I loved going on dates. I loved picking out what low-cut shirt to wear, what dimly-lit bar to meet him in and what whiskey I would order in rapid succession.

I was a first date professional—in the non-prostitution way, of course. I was quirky, sexy, hilarious and mysterious all at once. I knew what jokes to tell. I knew when to put my hand suggestively on his shoulder when, after the fourth or fifth scotch, he told me something that was so personal he had to look at me and then away, and then back again. I let him buy me drinks, but then offered to buy a round at the last bar. I ordered single malt scotch and admitted I was afraid of flying. He followed my lead and admitted, before the end of the date, how much he liked me. We parted ways hopeful, perhaps with a chaste kiss—that was more than enough.

I was like a sex addict in reverse. I never had sex.

After the first time euphoria wore off, after I walked home alone with the promise of a second date hanging over my head like a balled up cloud of anticipation, I would slump into bed and turn off my cell phone. I would begin to think about the date and how terrible it all was. He would leave a voicemail asking me out again and I would text him to halfheartedly agree.

The next day I would get cold feet. I would be reminded of a flaw—like that he said didn’t really read books; that he said he only read magazines. It would get stuck in my brain like bird shit on a windshield. I would keep going over it with my wipers, until it just streaked and I couldn’t see anything but bird shit.

So I would cancel.

It was all an equation, really. I multiplied my insecurities by my loneliness, added in my crippling fear of rejection and divided it by my gregarious need for attention.

I never saw the Writer or the Salesman or the Laywer again—not because of their flaws (and not because of the receding hairline, I guess) but because of mine. I wasn’t confident enough to secure a second date. Once my cover was blown, once the first date tango was over, I was just like the rest of the singles I knew floating aimlessly around the city and making up excuses. The only difference is that I assumed they were still having sex while I, home alone with my scotch and neuroses, was not.

I was so scared of being alone that I wanted to only be alone by my own volition. So I continued to go on first dates over and over again and expected different results. And it wasn’t until I realized my own bit of insanity would I find anyone else’s charming enough to manage a second date—never mind a full blown relationship.

It was an epiphany that would make my Jewish mother proud—and finally get me laid.