When Jess worries that she may not be a cool enough principal, she recruits Nick and "The Pepperwood Chronicles" to help make her popular with the students. Meanwhile, Schmidt hires an eager and overly-aggressive new assistant and Winston realizes that Furguson may be two-timing him.
Jess Day is an offbeat and adorable girl in her late 20s who, after a bad breakup, moves in with three single guys. Goofy, positive, vulnerable and honest to a fault, Jess has faith in people, even when she shouldn't. Although she's dorky and awkward, she's comfortable in her own skin. More prone to friendships with women, she's not used to hanging with the boys - especially at home. Of the three male roommates, NICK is the most grounded. He had big plans for life, but somewhere along the way, he stopped caring and became a bartender. Usually the smartest guy in the room, he has an uncanny knack for reading people and uses humor to deflect everyone and everything.
Schmidt is a hustling young professional who fancies himself a modern-day Casanova. Though his heart is usually in the right place, he's always scheming ways to climb the social ladder and is driven by an immature and almost obsessive urge to be on "the scene". Viewing Jess as a gateway into the elusive female mind, as well as a personal project, Schmidt encourages the guys to bring Jess into the apartment.
The third roommate, Coach, is a former high school athlete who currently makes his living as a personal trainer. Set in his ways and with a take-it-or-leave-it attitude to dating, Coach is most comfortable when he's in the gym. Though he'll never admit it, Coach's macho athletic exterior is actually a cover for his shyness around women, and he struggles to translate his personal confidence into conversation, preferring to speak in sports metaphors - or not at all.
Rounding out this group is Jess' childhood best friend, Cece, a deadpan, somewhat cynical model who blossomed after outgrowing her promiscuous adolescent years. She has the street smarts Jess lacks and spends a lot of time doling out no-nonsense relationship advice that only a professional model could give. She and Jess balance each other well and accept each other despite their faults, making Cece the perfect complement to Jess. As their relationships progress, the five friends come to realize they need each other more than they ever thought they would and end up forming a charmingly dysfunctional family.