In his new book, Sick in the Head: Conversations About Life and Comedy, Judd Apatow spoke with Amy Schumer about their experiences with the opposite sex.
FYI, Apatow and Schumer also worked this particular bit into an early sequence of Schumer’s new movie, Trainwreck.
Judd: But those experiences are funny. That’s the thing. Your worst sexual experience can be so humiliating and hilarious, both in movies and in stand-up. They’re always the best stories. A guy who has got a lot of terrible sex stories is the best dinner companion of all time.
Amy: It’s the best. I did one last season on my show, about the biggest penis I’ve ever encountered. It was like, that year I was single and I hadn’t been single for four years. I dated a wrestler and there was so much preposterous sex stuff from that relationship, and then I happened to go out with a guy and realized that his penis was way more than I bargained for. I probably already told you who the guy was, but he was an athlete. He was this guy my sister loved, a hockey player. I don’t watch sports but we winded up going out, mostly because my sister was like, “Oh my God, you have to go out with him! I’ve had a dream about you two falling in love!” So I go out with him mostly so she would think I was cool, but he was really hot and it was fun. I was like, There’s no way he’s going to be attracted to me. He could have sex with supermodels. So at the end of the night, I said, “I’m going to get out of here because I feel like a little insane with you.” And he was like, “No, I’ll go with you.” We went to another bar and then back to his place and—what happened with his penis, it was just so horrible and embarrassing.
Judd: I haven’t heard that bit.
Amy: You’re supposed to be really excited about a big penis, but when you’re faced with one, it’s like a unicorn—in theory, you’ve always wanted to see one up close but if it were ever standing in front of you, you’d be like, Fuck that, and you would run. You’d be like, Oh, it’s actually a horse with a weapon on its head. But in the moment, I was like, No, you have to do this. Everybody talks about how great it is. And I was like, okay, and I have a bunch of jokes in there about him going down on me because he was raised well but then I just realized that the guy has to do that, I mean he’s like lighting candles. This guy needs to get the girl relaxed. And then he kind of pulled it out and acted like it wasn’t a big deal. He was almost whistling like I wasn’t going to notice. And then I tried to get myself psyched: You can do this! You played volleyball in high school!
Judd: You have to slow your heart rate down. Like a Buddhist monk.
Amy: And then I say, “Do you have a condom?” He says no. And I was like, Way to call my bluff.
Judd: They don’t make condoms that big.
Amy: So then we tried and it didn’t work at all. It was not a possibility. I would have had to alter my body.
Judd: He must be used to this, right? He must know it’s going to happen.
Amy: At one point, I say to him: “Are you serious?” He’s like, “No, it’s usually—” And I’m like, whatever. In my twenties, I would have given it the old college try, but I’m in my thirties now and I was just like, I have Olive Garden leftovers in the fridge, see you later. It’s not happening. I’m not going to walk around New York with a gaping vagina because I had sex with you once.
Brad Richards – Detroit Red Wings
Married to Rechelle Jenkins now