Stoller can trace his comedic beginnings back to his childhood, during which he was “obsessed with comedy.” He remembers watching "Saturday Night Live" and thinking he wanted to become a writer for the show (rather than an actor, like most kids might). At eleven years old he discovered and began to imitate the unlikely choice of syndicated Miami Herald humor columnist Dave Barry. “I read a book of his when I was a kid and it blew my mind. I couldn't believe you could just write funny things and make people laugh. That's what inspired me to start writing. I was eleven and I started to rip [him] off. Writing about how hard marriage is.”
A lover of romantic comedy in particular, Stoller is taken with the comedic potential in the way couples communicate. “I love watching how people who are in love with each other deal with each other. Every time I've had a fight with an ex-girlfriend, at the time they're horrible, but when I look back they're often funny and weird, and that kind of stuff makes me laugh.” In describing his sense of humor, he explains, “The more real it is, the funnier it is. The more awkward it is, the more people are stumbly, the funnier it is. I like a sharp joke, but it has to say something that someone would actually say.” When he was younger, Stoller aspired to make movies similar to those of James L. Brooks or Woody Allen, “movies with a lot of heart. Because with heart it's even funnier.” He names “Broadcast News,” which he considers to be pitch-perfect, among his favorite films and greatest influences. “Watch it, and you'll be like 'Oh, that's where these guys ripped everything off from',” he says, presumably meaning himself, Segel and the young stablemate comedians who circle the Apatow satellite.
He grew up in Miami during “Scarface times,” and though it was “sports-oriented and outdoorsy,” he was able find a nerdy group of friends to run with that, according to Stoller, was ethnically diverse enough to resemble a Benetton Ad. After years of bowling and wandering the walkways of shopping malls, South Beach became a destination. But they didn't attempt to go clubbing, as their peers might have. “We were too nerdy. We'd just go and eat dinner and walk around and awkwardly drive home.”
Once high school-aged, Stoller left Miami during the academic year for the lush grounds and old red brick of Saint Paul's, an episcopal boarding school in New Hampshire. He is careful not to disparage it, but describes his experience there as being difficult largely because it was waspy, and Stoller, who is Jewish, felt out of place. “It’s a point of reference they all have that you don’t have.” He recollects a friend of his summing it up nicely, saying, “I didn't realize I was Jewish until I went to boarding school.” While he eventually made great friends, Stoller views the experience now as akin to being tossed into an ocean, and emerging knowing how to swim.
“The huge advantage of boarding school is that it throws you into the social fire. Every social interaction I've had since then has been a million times easier.” He adds, with a slightly bitter laugh, “Literally ever since then it's all been child's play.”