Playboy.com: In June 2002, you were a high school senior in New England. By November you were a Hollywood player. How did that happen so quickly?

Olivia Wilde: I got an internship with the casting director of The Girl Next Door. I would hold the clipboard and help them in their casting sessions and get them lunch. They were looking for a character, the bitch at school, and I happened to be there every day and knew all the lines, so the director's like, "Let's give it to Olivia!" It was really funny because that movie had the porn twist and then I went right into Skin.

PB: On Skin you played a porn king's daughter dating the D.A.'s son. On The O.C, your character plays both sides of the fence. Have you ever had a serious relationship your parents disapproved of?

OW: I went through a phase when I was 13 where I would only fall in love with people over the age of 19 or 20. I never had a real relationship with any of these people, but it was definitely the guy I wanted to hang out with and wanted to go on trips with. I would be like, "But, Daddy, he's a musician!" [Laughs]

PB: Is that when they sent you off to boarding school?

OW: When I was in seventh or eighth grade, I started developing my rebellious streak and started taking some trips on my own to New York and Philadelphia and just kind of taking off and doing my own thing. Not because I didn't like my family, but because I was just really restless. Maybe that was part of the reason I was encouraged to go to boarding school. But the other part was I just wanted more competition, and Andover had a really great theater department, so that's how I ended up in New England, but I was definitely not happy to be thrust in the suburbs of Massachusetts.

PB: How else did your middle school rebellion manifest itself?

OW: In seventh grade I shaved the back of my head. I had piercings when I was 11. I got a tattoo when I was 13. I did all kinds of typical stuff. I was not a crazy punk, but I was definitely into being an individual and doing anything I could to stray from conformity. It's a typical part of adolescence, but I thought I was special. So I ended up in boarding school, where that wasn't allowed to happen, and they whipped me into shape. I hardly made it through; I think my parents were just glad to see me at graduation. [Laughs] No, I ended up doing really well, and I did a lot of theater. I became the producer of their student theater department.

PB: Any wild boarding school stories?

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