Everyone gets everything he wants. I wanted a mission, and for my sins, they gave me one. Brought it up to me like room service. It was a real choice mission, and when it was over, I'd never want another.
- Captain Benjamin L. Willard, Apocalypse Now
Confidence is a funny thing. I never had it as a kid. I had to take steps to develop it. I did this by reading a whole lot of “Pickup Artist” material while in high school. It was the perfect time to do it because, at the risk of sounding like a hipster, it was before the VH1 reality show. No one could call me out for “peacocking” or for implementing “cat-string theory” because those terms weren’t in the mainstream yet. And while I certainly don’t consider myself a “pickup artist” by any means, having those tips and tricks at my disposal definitely helped me to develop the confidence necessary to approach girls.
That being said, the most important thing PUA taught me wasn’t how to approach women, but rather that it was okay to walk away. Every guy knows what I’m talking about, and every girl has been on the receiving end of this. A typical scenario involves a guy hitting on a girl and even after she’s expressed her disinterest he continues to hit on her, either oblivious to her rejection, or out of some delusional belief that he can still win her over. Most guys are raised to believe that girls have all the power. It’s our job to seduce them, rarely the other way around. They then have the option to accept or reject our advances. We forget that it’s still up to us to choose which girl to approach. So really, the best thing I got from PUA was the confidence to walk away from a girl I wasn’t interested in because I knew I could approach another one.
This brings me to the summer of 2010. I was in Chicago for a long weekend visiting law schools, which is to say that was the excuse I gave my parents so they would partially fund my weekend vacation. I spent the days exploring the city and the nights exploring bars. I was on a mission: No contact with friends, just me and the city. Not exactly an adventure befitting Survivor Man, but I needed to see if I could pick up girls in a foreign environment without the aid of a wingman.
I walked to a bar a few blocks from my hotel and immediately spotted a cute girl sitting alone.
“Are you drinking a Cosmo?”
“Yeah, how did you know?”
“There's not too many red drinks served in martini glasses. So, what, you're like a big Sex and the City fan?”
“Yeah, I love that show, but that's not the only reason why I drink Cosmos.”
I order a Jameson straight up. “Of course not. It's a tasty drink.” She's already defending herself to me. This means she cares what I think of her. “I'm not from around here. What's there to do in this city?”
“Honestly, I spend most of my time at school. But there's a lot of great bars in the area. The House of Blues is really cool.”
“What are you studying?”
“I'm a marketing major at Loyola.”
“Interesting; what do you want to do with that?”
“I really want to get into advertising. I love art and want to do something creative.”
I order her another Cosmo, she thanks me. “So you've probably read every book Donny Deutsch has ever written, right?”
“I don't know who that is.”
“He's a big time ad executive. He's like the Donald Trump of advertising.” Noticing the blank stare she’s giving me I continue. “Never mind that. You said you were into art. What's your favorite period?”
“What's your favorite era of art? Renaissance, Baroque, Romantic, Realism, Impressionism...”
“Oh, I like the Renaissance.”
“Out of all the art movements why is that your favorite?”
“I don't know. Just a lot of great stuff came from that era.”
“You probably like da Vinci then.”
“Yeah, he's really good.”
I take a second to reflect on what I'm getting myself into. A girl who supposedly got into marketing because she loves art thinks Leonardo da Vinci is good. “Yeah, da Vinci was pretty revolutionary. You know he was really into geometry. Looking at his work is like a Where's Waldo? of geometric shapes.”
I can't take anymore of this. I take out of my phone and pretend to be reading a text. “Oh shit!”
“I'm sorry I gotta get going. Hillary Clinton needs a consult on the imprisoned journalists in North Korea.” I down my whiskey and begin to walk away.
“Wikipedia it, you'll be fine.”
Guy: On the other hand, you take a guy like George Washington Carver. The man devoted his whole life to the peanut. Imagine having so much passion for something. I've often wondered if he ever worked with the pecan.
Elaine: Yeah, me too.
Guy: Now is that considered a nut? Because I know the cashew is a legume.
- Seinfeld, "The Stranded"
Guys are scared to walk away from a bad pick up for the same reason shareholders throw good money after bad into shit investments. Both worry about waste. The guy trying to pick up a lost cause—either because she shows no interest in him, or because he realizes he has no interest in her—is worried about the time and money he will have wasted if he doesn’t succeed, or he just really wants to get laid. The investor worries about the same, though probably not so much about the getting laid part as it relates to the investment. Knowing when to fight and when to walk away is vital for survival in relationships, finance, and life in general.
The first thing to keep in mind is never fall prey to the sunk cost fallacy. The conversation with Stupid Cosmo Girl was painful, and I know myself too well. I have many smart friends who have learned to shut off their brains with the aid of any number of substances. I can’t. The more I drink, the less I’m able to suffer inane conversations. There was no attraction anymore. No point in escalating.
If after getting to know the girl you want to reject her, have fun with it. There are many ways to end a conversation. I went with the Confuse-the-Shit-Out-Of-Her-and-Bolt Method. The problem with rejection is feelings get hurt. No one wants that—unless of course you’re an insecure, sadistic prick. You aren’t, right? If you do this part right, she may never know that you rejected her.
And always keep in mind that even if you don’t get laid, a good hotel bar can salvage a bad night. Followed by The Dark Knight at 3am on HBO.