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 avoids her feelings for Nick by taking care of her dad in Portland. While attending a work party with Reagan, Nick panics that they really don't know each other. Meanwhile, Aly prepares to meet Winston's mom for the first time, as Winston admits he hasn't told her they are cops.