I used to have the worst “date game” of any guy you’d meet. You see, I’d approach a woman, talk to her for a while, get her phone number, and then go out on dates. I’d then never hear from her again.
What went wrong? How could I be such a failure? It didn’t make much sense to me until one chance conversation changed everything.
“Line up on the right hand side, next to the wall,” the ticket guy at a local concert exclaimed. I felt the staff was being a bit oppressive and said, “Man, this reminds me of the time I was in jail!”
Two girls looked back and smiled. I had never seen a girl’s eyes light up so brightly. “Oooooh, you’ve been in jail,” the blonde one asked.
Once we got inside, I hit the two friends up. I told them that I had been in jail and they had never been so impressed. The brunette squeezed my arm, signaling to the blonde that she had chosen me.
I talked to the brunette for a while. She wasn’t some trailer trash girl who had been raped by an uncle and thus bore an attraction for bad boys. She was well-travelled, had a six-figure job, and her brother worked for a national law firm. She was, as far as chicks go, just a “regular,” “normal” and “cool” girl.
Yet the only reason we hooked up that night was because I had been to jail.
Can I talk to you about jail for a second?
Going to jail is not fucking cool at all. If you’re arrested while driving, your car will be impounded. When you get out, you’re going to have to track down your car and pay close to a grand (in cash; those impound lots don’t take checks or credit cards). I was arrested while at work. That is every bit as awkward as you’d think.
You walk into a holding cell with a bunch of filthy meth heads and scum bags. If you’re lucky, the jailers hand you a brown paper bag containing a sandwich – two slices of white bread with a piece of proceeded “meat” in between.
You’re stripped searched. You’ll bend over and spread your ass cheeks while another man looks inside to see if you’re smuggling drugs or cell phones in your anal cavity.
You’ll share a cell with another man. This means listening to him breath, snore, and take a shit in the middle of the night.
My cell mate was an obese trucker who had been arrested for (I assume) sex with a child. Fyodor Dostoevsky was right: Men have a need to confess. “I really fucked up this time,” he said as a way of opening a conversation with me. I put on my Russian serial killer face and looked right through him.
(I had requested solitary confinement, as going insane alone in “the hole” would be far preferable to listening to a child molester put “Hersey squirts” into the toilet.)
If the charges are serious, you’ll need to raise substantial cash to get bailed out. If you’re younger, this means a call to dad and mom or grandma and grandpa. You’re making collect calls to various people to get someone to get your grandparents to Western Union them cash. Now those who love you the most are sick with worry.
So, like I said, there is nothing cool about being in jail.
Yet being in jail changed my game forever.
On dates I no longer asked girls what they were interested in. I didn’t talk about my hobbies or the last book I read. I didn’t talk about my life story – which is actually pretty interesting.
On dates, I didn’t seek intimacy or try creating a connection by seeing if we had shared interests or values.
I just stayed in shaped, dressed nicely, nodded my head, smiled occasionally and talked about – nothing, stupidity, and bullshit.
Suddenly I was able to go from never seeing a girl after a date to often banging her the same night.
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