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The Funny Side of Love

Kaling with Novak on The Office.  

Kaling grew up in Cambridge, Massachusetts, where her mother is a doctor and her father an architect (they played her parents on one of her Office episodes). After graduating from Dartmouth, she and her friend Brenda Withers wrote a two-person play called Matt & Ben, a humorous take on how Matt Damon and Ben Affleck came up with Good Will Hunting (Kaling played Affleck). They took the play for a short run in L.A., where it was noticed by Office producer Greg Daniels. Her character on the show, Kelly Kapoor, is a vapid customer-service representative who has an encyclopedic knowledge of celebrity breakups and romantic comedies. “Anytime I play a role, it will just be a version of myself,” says Kaling, following the path of her comedic role model: “People assume it would be Tina Fey, and she is a great hero of mine, but Woody Allen is really the ultimate. I love that he believed in himself enough to do what he did. And I have that same feeling—that there’s nobody that looks like me in movies, nobody would cast me as a romantic lead, but I want to do it and I feel confident that I can.”

Kaling’s goal is to write the classic romantic comedy for her generation, where women are as into the NBA and true crime as they are into searching for love or the perfect pair of shoes. “I’ve led kind of an interesting life, and I drink and party and I am funny and have a good group of friends. And I wonder, why isn’t that on TV or in the movies?” Her favorite romantic comedy is Nora Ephron’s You’ve Got Mail, the film about love found on the Internet, starring Tom Hanks and Meg Ryan. “I saw it when it first came out,” she says “when I was an intern at Late Night With Conan O’Brien. I was 18 and very intimidated by New York, and this movie made me fall in love with the city.” She admires the film for its restraint: “A lot of romantic comedies now have to be R-rated sex comedies. Do you even see anything other than Meg Ryan’s wrists in You’ve Got Mail? She dresses like a female comedy writer—nothing is fitted, everything is four sizes too big.” Kaling watches the movie in fifteen-minute intervals, “when I’m doing sit-ups after a run or something, and it’ll cheer me up. That and The Fugitive. Whenever that’s on, even the last five minutes, I’m in.”

The Low Self Esteem of Lizzie Gillespie, currently in preproduction, is Kaling’s first big-screen stab at her fantasy. “It’s about a girl who gravitates toward ugly losers because she thinks she’d never be able to date anyone attractive and cool.” The focus, she says, is “80 percent interaction between three female friends. Judd Apatow was really onto something when he wrote movies where guys actually talk the way guys do. I’ve never seen that done with female friendships. Every so often, Hollywood tries this thing of, ‘Girls are just like guys! They talk about fucking and sex!’ I mean, I don’t necessarily go there with my friends, nothing that lurid.”

Kaling vows to do away with dumb conventions that drive her nuts: “Why do all the women have to be klutzes? All these pretty women with no discernible flaws, so let’s make them a klutz! Or what about all the skinny women shoving food in their mouth on dates? It would be so much funnier if the women weren’t skinny. That’s a great Onion headline: ‘Actual Fat Woman Shoves Food in Her Mouth in Romantic Comedy.’ ”

The Office
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