Writing for Esquire was such a great job, nobody ever left. When I arrived in 2002 at 28, I was the youngest writer there. When I left in 2016, I was 43… and the youngest writer there. I’d often get assigned “young” stories and feel like a complete narc: “Hello, fellow kids.”

In 2009, I was supposed to profile Taylor Swift. I didn’t even know if she was a boy or a girl. (She was a girl, the Internet told me. A 19-year-old girl.) I was 35. I dreaded hanging out with her. “So, do you like horses?” Thankfully she bailed and I wrote about Roger Ebert.

In 2011—now I’m 37—I had the same uneasy feeling when I got assigned Justin Timberlake. He had a movie coming out, and I was to meet him after he appeared at Comic-Con. I flew to San Diego in a complete sulk. What the hell am I supposed to talk about with Justin Timberlake?

I knock on his hotel room door. He answers. His eyes are alight. “I wanna go back to Comic-Con,” he says. He opens his closet. There are four low-rent costumes inside: Cookie Monster, Elmo, Ernie, and Bert. “Let’s do Bert and Ernie,” he says. “It will make for better bonding.”

I nod. “You’re Bert, okay? Is that cool?” I nod again and we’re soon both in our underwear. I have known Justin Timberlake for 120 seconds. “I can’t believe how quickly you got my pants off,” I say. He shrugs: “It’s a gift.” I fall profoundly in love with Justin Timberlake.

Our broke-ass costumes don’t have pockets. He tucks his money in his sock. I’m wearing flip flops. I put mine in my underwear. We walk to the hotel elevator. A young couple beam when they see us: Bert and Ernie! They have no idea they’re beaming at Justin Timberlake.

We head out into the crowds. He has not walked in public without security in seven years. I can tell he’s nervous—his massive orange head on a swivel, his legs trembling inside his highly flammable pants. But we’re greeted with affection everywhere we go. It's the best time.

We start posing for pictures. “I keep forgetting,” he says. “It’s because I’m Ernie. It’s not because I’m me.” We’re posing with a 13-year-old girl and I ask him to take his head off and watch her spontaneously combust. “No way, dude,” he says. “You have no idea what it’s like.”

My new best friend Justin and I tour Comic-Con. We hear one of his songs in front of The Avengers booth. It’s like a great inside joke. “I can’t believe they’re playing one of my songs,” he says. “You’re witnessing one of the most unforgettable days of my life.”

I was moved, too, watching this man—just a guy, a pretty regular guy but with the talents and looks and good fortune to make him really super famous, and he hasn’t been outside by himself in seven years. It was like watching someone walk out of prison, or come back from space.

We head back to the hotel elevator. It was wrapped in giant ads for True Blood. There was a guy dressed like some kind of bird. I took off my Bert head to get some air. Justin left his on. “This is a very strange scene,” the bird said. “Buddy,” I say, “you have no fucking idea.”

Back in Justin’s hotel room, back in our regular clothes, I feel bonded enough to ask him a question I wouldn’t normally ask. “So," I say. "When you’re having sex with Jessica Biel… Do you ever look down, or up, depending, and think, HOLY SHIT, THAT’S JESSICA BIEL?”

Justin Timberlake smiles: “I mean, not the way you would.” We say goodbye and return to our separate lives. Esquire puts out a call: Did you take a picture with Bert and Ernie at Comic-Con? Can we have it? Because you took a picture of Justin Timberlake and some old, fat writer.

This is a picture of Justin Timberlake and me. He is on the left.