In my late teens, I knew a man who was a sort of mentor to me. His name was Jack, and he had slicked back black hair and often wore polo shirts and khakis. He would always be smoking his Marlboro Lights when we talked, even if it was indoors. One day, while I drank ginger ale and he had himself a glass of scotch, neat, he asked if I was dating anyone. I told him no so then he asked if I liked anyone in particular. If I was infatuated with anyone. I told him there was a girl at school, Lauren, who I thought was really pretty. When he asked what was keeping me from dating her, I told him that she was probably out of my league. That I might not be her type. That it would be a waste of time to ask her out.

Jack nodded and took a few sips from his glass while we passed a minute in silence.

You should still try, he finally said. Does she have a nice body?

I told him that she was maybe a few inches shorter than me. Nice, round ass and perky tits. That she was pale and had a face you could never get tired of looking at.

You guys talk often? he asked. I told him that we had interacted in class a few times, but nothing more than on school-related matters.

I see, he said. He lit another cigarette and asked if I wanted more ginger ale. I told him I was okay.

Don’t be afraid of girls, he said. Especially the hot ones.

I nodded, hoping he would tell me more. But he didn’t say anything and kept drinking his scotch.

The next time I saw him, he asked if I had tried asking Lauren out. I told him that I hadn’t.

Give it a try, he said. Even if she says no, she’ll still feel good about it.

How about how I would feel? I asked. It would suck to get rejected.

Don’t worry, he said. You’ll get rejected many more times in life. It’s a good feeling to get used to.

Any tips on how I should approach her? I asked, knowing he had dated some attractive women in the past. He shook his head and puffed on his cigarette. Just be nice.

That’s it? I asked.

If you get really nervous, just tell yourself that in ten, fifteen years – maybe even in just five – she’ll be thicker, he said.

Thicker?

Yes, thicker.

***

I ended up dating Lauren for more than four years. Had it not been for my move to San Francisco and our ill-fated attempt to keep our relationship long-distance, things may have been different for us, but to be honest, I think it was for the best. A few years ago, I saw a video clip of her and her new husband in the Weddings & Celebrations section of the New York Times. She looked great and seemed extremely happy. She didn’t look thicker at all.

Jack died in a drunken driving accident not too long after I started dating Lauren. He never got to meet her. I think he would have been proud.