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The classic wellspring of comedy is a miserable childhood, but growing up in Cambridge, Mass., Vera Mindy Chokalingam was a contented kid, if not a popular or particularly social one. "When you're a boy and a nerd, you deal with more bullying," she says. "As a girl, you're sort of overlooked." She is one of two children of Indian-born parents--Dad is an architect, Mom an ob-gyn--and the passages in her book about her childhood and family are suffused with warmth and nostalgia. In high school, she'd spend afternoons in the basement writing "Wayne's World" and "Weekend Update" segments, print them out on her parents' computer and fall asleep reading them to herself on the sofa. "She was a satisfied, happy nerd, and we all encouraged her," says her brother Vijay Ingam, a 34-year-old financial analyst. "I think my parents realized when she was in high school that Mindy wasn't going to take a conventional route. But the chick could write--that was one thing my parents recognized. I was two years older than her, and she helped me with my college essay."
In some ways, Kaling's humor is that of the indulged kid whose parents laughed at her every bit and gag. "She's this funny, well-loved child who never outgrew it," Novak says. "She was used to her family watching her and laughing at her, so that's how she is in the world."
She had an equally receptive audience at Dartmouth, where she was a campus theater star--"Jaws in a community swimming pool," as she writes in Is Everyone Hanging Out Without Me? But in New York City, where she moved after graduation, she was a much smaller fish in a much bigger pond. Broke and living in Brooklyn, Kaling improvised a series of dialogues with her roommate Brenda Withers. "We didn't have any money, so to amuse ourselves we would pretend to be different people," Withers says. In a bit called "Baby Raccoon," a dead baby raccoon's friend tries to wake it up with cooing, purring and various other animal noises. In another, Kaling and Withers played the pre-fame Ben Affleck and Matt Damon, respectively. "We would walk around Prospect Park nonstop and speak as Matt and Ben, imagining their friendship, their rivalry," Withers says.
They eventually shaped that material into the sarcastic, surreal two-woman show Matt & Ben, in which the duo's big break arrives when the Oscar-winning screenplay for Good Will Hunting literally drops from the ceiling. Kaling and Withers opened the play at the New York International Fringe Festival in 2002, winning over downtown audiences and attracting the interest of television agents and producers. The 24-year-olds moved to Los Angeles to work on a sitcom pilot based on their lives in Brooklyn, a process Kaling describes as "sitting in a room with a group of actresses who bear a passing resemblance to you but are much, much thinner and more conventionally attractive." She was relieved that the pilot wasn't picked up as a series--and even more delighted that a producer who had seen Matt & Ben, King of the Hill co-creator Greg Daniels, wanted to hire her for an NBC sitcom. It was based on this British show that Kaling had never seen, called The Office.