The book contains a wide range of stories that chronicle a variety of work, love, and life experiences about everything from the Shy Pooper (a guy who couldn't use the bathroom with her in the apartment) to gay ex-boyfriends to cat acne. But the story does continue to return to her complex, sometimes beautiful, often infuriating relationship with the ex-boyfriend who went on to immortalize her ass in print. Though he and the title of his book are never named, Winston's story is emotionally revealing, easy to relate to, and always hilarious.
Back Stage: Did you always think you would write a book someday?
Hilary Winston: No! I love books and I love to read; I was always that kid who, instead of taking stuffed animals to bed, I took books. But I always kind of thought smart people wrote books. Not that I think I'm an idiot, but I figured smarter people than me wrote books. But this really felt like the only way to tell my story. And I realized there are a million guys like him who don't write books but, because they did the breaking up or they didn't call the girl back, they write the history. They're the victors. And I thought: For all those girls on the other end of the guy not calling them back, I'm going to tell those stories. So most of the stories in my book aren't about me breaking guys' hearts and being victorious, it's just me saying, "Yeah, on the other side of your story, there's a real person. The girl you joke about with your buddies, she's a real person with thoughts and feelings."
Back Stage: When did you realize you had a book?
Winston: That was hard to figure out because at first, I realized the whole book couldn't be about him. So I thought I might explore other relationships and started writing down stories. That's how it ended up being essays—someone would say, "Remember that Shy Pooper story? That's really funny." So I would write that. And I put it together and it was disjointed and weird and half the stuff was about my ex and half the stuff was about other people. But my book agent really felt that memoirs sell, so I tried to do that, but it just didn't feel right. So I liked the idea of it just being snapshots of my dating life and life with my ex. And they all added up to tell the story of what it was and why it ended.
Back Stage: Did his book do well?
Winston: Yes, it did. It wasn't a bestseller or anything, but it did well. It's weird, because you don't want them to fail. My ex is a lot of things, but he is a good writer. And I never want to begrudge somebody who works really hard their success. But it's just hard, you want it to exist and happen without having to see it. And I'm pretty honest about the fact that I wanted him to be unlucky in love.
Back Stage: Your ex-boyfriend isn't [author] Tucker Max, is it?
Winston: [Laughs.] No. It's funny: Tucker Max comes up a lot in interviews, so I decided I would buy his book. I got it on my Kindle so nobody would see me reading it. It is so terribly written. In my head, I always thought, "The guy is a creep and I'm sure it's just cheesy, gross stories about getting drunk and having sex with slutty girls, but he must be a smart guy. But he went to Duke, and I'm sure the writing is good." But it's not. He's an awful person—which I know is his point—but he's an awful person who can't even turn a phrase!
Back Stage: You came up through The Groundlings; were you ever interested in performing, or has it always been about writing?
Winston: I did The Groundlings and the whole point was to get through the writing lab so I could write my own stuff. I do think it's good to have a little performance background. I did sketch comedy and improv in college, and it helps you in writing and thinking about how the actors work. I think every writer has a little bit of a performer in them. But I am amazed and impressed by actors; I think it is so hard to pursue. I had a great experience there. I met a lot of people and it made me feel like I was at graduate school for Hollywood.
Back Stage: How did you land your first agent?
Winston: Somebody from my Groundlings cast pulled me aside and said, "I write on 'South Park,' but I don't want anybody to know. My agent's assistant is being promoted and he's looking for people, so I'd like to recommend you." So I ended up being one of my agent's first three clients and we've all done really well. His name is Mickey Berman. He's at ICM, and I hit the jackpot in getting somebody who got my sense of humor and is also a good person.
Back Stage: What's the best advice you've gotten as a writer?
Winston: There was a guy at an early job who gave me some of the best advice of my career. There was strike talk and I was nervous and things were heated and I cried at work. He said, "You have all the cards stacked against you as a woman in comedy. You cannot cry. A guy can express way more emotion but you cannot. I'm not saying you don't have a reason to cry, but you need to know that." And I learned so much from him; he was a really great guy. And three years later, he killed his wife. And what do you do with that? Someone who had been so wonderful to me and given me so much—how do you think about that person and their advice when something like that happens?
Back Stage: Oh, my God. Where is he now, did he—
Winston: He's in prison, yeah. I just had to compartmentalize in a way, realize it was great advice and take it for what it was.
Back Stage: How did you land the job on "Community"?
Winston: I have a deal at Sony and they had loaned me out to work on "My Name Is Earl," but they really wanted me to be on one of their shows. I loved the pilot for "Community" and had a strong feeling of what it could be. I met with the creator, Dan Harmon, and we really hit it off. And it was such a great cast. And I wasn't wrong; it's been a great experience. It's definitely the hardest job I've ever had. We're constantly throwing things out and coming up with new things. We work really long hours. Every week we're trying to do the best episode we've ever done.
Back Stage: How do you respond when someone says that women can't be funny; like in that Christopher Hitchens "Why Women Aren't Funny" piece a few years back?
Winston: Some guy comes out every couple years and says that. Yeah, some women aren't funny. And some guys aren't funny—how about every guy I've been on the past 10 dates with? I think there's less funny women because when you're in school, you're not encouraged to do any of the things that make you laugh at that age: fart jokes, acting out in class. In junior high, putting yourself out there is what you have to do to get laughs and women are so self-conscious, they're worried about their bodies, they're getting their periods, so the last thing they want to do is draw attention to themselves. And you're constantly being judged on your looks and it's hard to be classy and cool and be making jokes. There's very few women who are funny and glamorous. When you're trying to be pretty and get asked to prom, you're not the girl who has the funny retort or comeback to a guy. Those skills aren't encouraged at all.
Back Stage: You're adapting the film version of your book for Paramount; what's the status of that?
Winston: The movie pitch sold at the same time as the book; it sold off the book proposal. It's at Lorne Michaels' company. But it's really fictionalized because the book is not cinematic and people are sick of hearing about writers in Hollywood. So I set it in Washington, D.C., where I lived when I was working for NPR, and used other things from my real life, but made the story different.
Back Stage: Has your ex read the book?
Winston: He has. We had lunch a couple weeks ago and it is weird to think about how far we'd come as writers. We had struggled and supported each other in those early years. Now we were sitting there with his third book about to come out and I have a book coming out. It was really cool; the one thing we were both right about was to bet on each other. And we both did always believe in each other, and we were right.