Evan Cheson was actually a charming and good-looking man. He had a full head of thick, black hair; blue eyes; an athletic, six-foot-one build; smooth, dark eyebrows; and facial features suggestive of his French-Italian ancestry. And for most of his adult life, he had been a confident and successful man, from school, to work, to women.
But several major failures in rapid-fire succession can inhibit good judgment, and thereby invite more failure. For Evan, losing a job and a girlfriend, each via email, one day after the next, was too much to avoid the absurd downward spiral that would ensue. He even avoided checking emails for a while, but that didn’t help.
On Thursday night, after a few months of fruitless rebound attempts and embarrassing faux pas with women, there was something perverse in Evan – maybe even carelessly self-destructive – that wanted to know just how laughably low he could go.
So he put on a new pair of dark slacks and a collared, button-down, sky blue shirt just snug enough to suggest his occasional gym routine. His clean look – with a dab of cologne, a gargle of mouthwash, and freshly polished leather shoes – was calculated to minimize the entrance hassle into Manhattan’s clubs. But had Evan fathomed just how hard he would end up crashing that night, he would have surely stayed home in his T-shirt and boxers.
Chapter 2
Evan Runs Full Speed into the Wall Ahead
It began in a bar. The Bowery Bar. It was the end of summer – an auspicious time for an unattached twenty-nine-year-old male in Manhattan. Scattered sparingly about the spring, summer, and fall, there are about fifty days of perfect weather in New York City: zero humidity, clear skies, and seventy-five to eighty degrees fanned by a light, cool breeze. During such days, smiles sprout more readily, clothes pronounce rather than protect, and the sweet scent of promise wafts everywhere in the air.
The last day of August 2000 was one of those perfect fifty days. And it was a Thursday, which meant that most of the Manhattanites leaving the next day for a weekend in the Hamptons were still in the city, and that meant more female prospects for Evan. Indeed, that Thursday felt so promising that Evan thought he might finally reverse a dry spell that somehow felt longer than his postpubescent years. But Evan’s new insecurity, which resulted almost entirely from his recent bout of bad luck, made him somewhat desperate to prove himself any way he could. And as his desperation led to ever greater and more frequent fumbles, he began to question the quality of his goods, as even the most steadfast traveling salesman does after enough slammed doors. He lost his touch, hesitated with his humor, and forgot some of the tactics that had served him so well in the past.
So when Evan spotted a woman across the bar who easily qualified as a “9+ hottie” in his book, he broke one of the most important rules of the pick-up: never wait more than a minute to make a move. A longer delay after initial eye contact suggests a lack of interest or – even worse – a lack of confidence. It also converts the interaction from the flowingly spontaneous to the self-consciously calculated. Evan’s five-minute delay before approaching a woman who absolutely attracted him was, in this case, attributable only to his three-month string of prior botches. To exacerbate matters, when he finally gathered the gumption to approach her, he allowed some form of autopilot to take over, in the hope that luck alone might produce some good results.
She was wearing body-tight, silk white shorts, and a pink wife-beater undershirt with no bra. Her perky, full breasts looked to Evan like two deliciously firm, cherry-topped cantaloupes, daring him to look anywhere else. The woman oozed sex and her name was Tina, although Evan would never actually come to learn this basic fact about her. He would instead remember her only as “the soft porn babe I massively underestimated.”
As Evan arrived next to her at the bar, he realized that the only thing about her that he had observed was that this sultry, petite blonde in his crosshairs had the figure of an exotic dancer or a soft porn actress. Evan’s autopilot skills were reliable enough to avoid a disastrous opener like, “Say, did anyone ever tell you that you could be a great exotic dancer?” But they were sufficiently lacking in foresight and imagination to realize that asking Tina what she does for a living might be just as bad, if she was, in fact, an exotic dancer. So when Tina turned and noticed that Evan had squeezed into the small space at the bar next to her, all Evan could say when she looked at him was “So…What do you do?”
Tina, who had noticed Evan hesitate for several minutes before walking up to her, just shook her head with a mockingly disappointed look on her face. “Couldn’t you do any better than that?” she replied.