Chapter 31

Being with the Crew had its perks. I got to party with the hottest girls in school. Girls I only gazed at from afar before, were now getting drunk with me. They were flirting with me. They liked me. It was surreal. They should have never let me get that first taste. The thrill from having a beautiful girl within reach, it changes you. I already had the desire deep-rooted, but now I was almost getting affirmation.

The operative word being almost. They may have been partying with me but I was still a long way from having a girlfriend. I still hadn’t even kissed a girl. Weirdly enough I did get that blowjob a year prior. Weird sequencing I know. But in any event, I felt like I had arrived.

I told Craig I liked Sarah. He said he knew. I’ve always been terrible at hiding how I feel, especially when I like someone. He reminded me who her boyfriend was and that I didn’t have a chance. He didn’t think I had a chance even if she was single.

“AJ, you can’t go from having no girls ever to baddest bitch in school. Start small. Date a random young girl first. Even if somehow you got Sarah, you wouldn’t know what to do with her. She’s too advanced for you.”

His logic made sense but how applicable is logic to a 16-year-old in love?

Sarah was the hottest girl, so of course, girls thought her boyfriend was the hottest guy. That’s tough competition when you’re at the bottom of that scale. At least I felt like I was.

There’s an interesting thing that happens to a dude who peeks young though. It’s often the worst thing, because it gives him a false sense of entitlement. He’ll think because things have always gone his way, they always will. Overconfidence is ironically a weakness. The tortoise and the hare.

Conversely when you start at the bottom, you never expect anything. You work twice as hard. You’re more appreciative for everything you get.


It was 9/9/99. The MTV Video Music Awards were on that night. Chris Rock was hosting.

Biggie and Tupac’s mothers presented an award together,

and Diana Ross played with Lil’ Kim’s tiddy.

The show just went off when I got a call from Craig. He said he had news that would change my life. He asked me if I was sitting down. I stood. I had a feeling what he was about to tell me. Sarah told him a secret.

She had a crush on me.

He gave me advice that’s still resonates, “just take it for what it is”. In Rick’s overconfidence he got caught cheating. She said she wasn’t looking for anything serious since she just got out of a relationship. That crucial piece of information went in one ear and out.

Before he hung up he gave me one last piece of advice. Perhaps it was more of a warning. Perhaps he saw writing on the wall. Right before we got off the phone, he said… “don’t fuck it up”.