Sam Greenspan - 11 Points Guide to Hooking Up: Lists and Advice about First Dates, Hotties, Scandals, Pick-ups, Threesomes, and Booty Calls

D amn, I wish I was a black guy.

As I stood there, alone, at a nightclub in Las Vegas that was the first thought that ran through my mind. (My second thought was: Or is the correct grammar, Damn, I wish I were a black guy?) I nervously sucked down an $8 Bud Light because I needed somethinganythingto do besides awkwardly cling to the wall, staring out at all the people dancing, like one of the nerds in an eighties movie wearing ruffled tuxes and thinking they have a shot at Molly Ringwald.

I love a good, under-the-radar stereotype, and heres one of the best: Somehow, it seems, black guys just dont have that same fear of rejection thats crippled me for oh-so-many years.

Of course, its not true across the boardIve had many shy black friends and, ya know, theres a cowardly lion in The Wiz but damn if I havent seen the scene play out too many times to count. A black guy, not necessarily good looking or charismaticin fact, often, neitherwalks up to a random girl, confidently takes her arm, gets her attention, and says some secret, magical phrase to her. Odds are, she rejects him. Wholly unfazed, he takes two steps over to another girl, confidently takes her arm, gets her attention, and repeats the process. This particular night in Vegas I watched this one guy work that routine with nine different girls until I finally lost sight of him in the crowd.

Lets contrast that scene with what happened to me, just moments before. Id seen a girl I thought was cute about a half hour earlier, while I was taking a lap around the club. She was with a large bachelorette party. I didnt say anything then, just raised my eyebrows in her direction and kept walking. Now, 30 minutes and zero women talked to later, I saw her again, this time on the dance floor. I decided that, this time, Id try to say something clever.

And that clever phrase turned out to be... Whos the bride? Not poetry by any means. But, in my mind, I figured thatd be a good enough in to start talking to her, and if she was at all attracted to me, wed be fine from there. After all, it was Vegas. Everyone gives you a little more leeway there than in real life.

Her, she said, pointing at the girl wearing the tiara and the sash reading Bride-to-be. Oh, I figured shed won the Miss USA pageant or something, I hilariously replied. So where are you guys from? Hold on a sec, she replied, then turned around and started dancing with a few of her friends. I spent about eight excruciating seconds standing there like a lost child before turning around and walking the other direction, trying (and failing) to look cool.

I retreated against the wall for a while, eventually met back up with a few friends, and ended up leaving the club to gamble within an hour. I would not say a word to another woman that night.

I can describe that scene in vivid detail because, to this day, every rejection Ive experienced, however nominal, still sticks with me.

I was an extraordinarily shy child, Im an only child who hates confrontation, and Im a former fat guy who still has self-esteem scars that burn like a Harry Potter plot device. All of those have collaborated to ensure every single rejection I endure is crippling.

Thats when I think of the black guy, who, in about four minutes, was rejected the same number of times that Ive been rejected in 10 years. And who probably kept on going until he finally found that one in 50, one in 100, who thought he was good looking or found his compliment genuine.

Im an extreme case, for sure... but not that extreme. I have extremely confident friends, confrontational ones, ones who werent only children, ones who were never fatall of whom are just as petrified of female rejection as I am. And when it comes to my female friends... from what Ive observed, if a woman breaks from societys natural order, hits on a guy, and he rejects her, shell downward spiral into a self-loathing shell even quicker.

Which brings us to the thesis of this entire chapter of the book: Trying to pick up and meet new people is soul-wrenchingly awful (unless youre a non-shy black guy).

But its something you have to do. Its a 100 percent necessity if youre going to live a single life thats not lonely, boring, and wasted. Because that single life is soul-wrenchingly awful in a different, and ultimately much worse, way.