John Cusack is Dead. Long Live John Cusack

I started going out with my very first “girlfriend” at the tender age of 16. In that relationship, which lasted all of 3 months, I was cut right out of central casting as the quintessential Lloyd Dobler wannabe, complete with the goofy perv trenchcoat and my trusty boom box. Me and my Diane Court would take the boom box and a blacket to go make out in a field next to an elementary school near her house. Like every 16 year-old boy since the dawn of man, I thought, almost exclusively, about “going all the way,” with a girl almost every moment of every day. The best part was I knew my Diane had “gone all the way” with her previous boyfriend, so, in my turbulent adolescent brain, this was a sure thing. Plus, I had been nurturing my smoking habit since I was 13 and Diane smoked too! I envisioned rolling off her in that grassy field and laying there, on my back and basking in my freshly dispensed virginity.

Too good to be true? It was. Diane dumped me and started dating some joker who worked at a hip used record store me and my gang frequented. Looking back on it, I am reminded of another John Cusack gem High Fidelity in which he ponders his first girlfriend, whom he basically had the same relationship I had with Diane. John concludes that “it would be nice to think that times have changed. Relationships have become more sophisticated. Females, less cruel. Skins thicker, instincts more developed … but alas, all my romantic stories are a scrambled version of that first one.”

I first started dabbling in online dating around when online dating was hitting the mainstream back in 2007. I naively ventured forth into the world of E-Harmony and Match like a 13 year-old boy walking alone into Target with a $15 gift card. What to buy? New socks? Sensible but boring. A football to toss around with my friends? Please. When I was 13, I had no friends and I sucked at football anyway. A thoughtful gift for my Mom for Mother’s Day? Sure, Because all 13 year old boys immediately of spending whatever disposable income they come across on other people. At age 26, the host of profiles at that first dating site promised women who “love life” and “love to laugh” and “love just hanging out.” I wrote an entire essay on the subject that I will never even try and get published because the very idea of online dating is so much a part of the American zeitgeist at this point that an argument against it withstands criticism and there’s really nothing I that can say about it that hasn’t already been said.

Now, 16 years after that first sojourn, I decided to venture out into the battlefield of online dating armed with a freshly jaded perspective on love coupled with cautious optimism. What I have banished from my arsenal, though, is the naivete I first brought to that first dating site. See, various aspects of womens’ profiles bugged the crap out of me. Woman who said they “wanted a friend” first irked me because I figured why would you be at a dating site if you didn’t want a romantic relationship? I also didn’t know at the time how many creepy, cringy, defeated and disturbed single men rove online dating sites. Perhaps the biggest noodle scratcher for me, though, was profiles of women which, as I would come to develop the skill to decipher, were written by men, for men, with photos of staggeringly beautiful women coupled with profiles that read as though the author used a EASL textbook as his only reference. I’m trying it again but this time, with the whole project at arm’s length. I got enough going on in my life a solid 9 months after my last relationship crashed into a fiery abyss that I can afford to have some fun with the project and, really kind of learned that I have to because shortly after the first date I went on with a woman I met online, she texted me two days later and criticized my teeth.

So, I went back to a site that me and several friends have met women on, punched up a very Buddhist sounding profile just to, as Jim Norton said, weed out all non-hackers who do not have the year it takes to serve in this beloved corp, and wouldn’t you know it, about a week after I signed up, I got my first message from a woman that fits the profile I referred to earlier like a glove. She/he also seemed to have a picadillo for an app called Hangout. She had the requisite photo of a beautiful young women and listed in her profile that she was from Miami. So I started out by asking her about that.

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She seemed unphased by my faux concern and said something the woman in the profile wouldn’t likely say. At which point I just decided to dive in and have some fun with this guy, starting out my establishing my self as John Cusack in Gross Pointe Blank and riding it out from there.

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