Schmidt tutors Jess in the not-so-fine-art of dating via mobile apps. Meanwhile, Winston is desperate to make a good impression on his fellow police cadets, which backfires when Nick, Coach and Cece show up at a party thrown by fellow officers.
Jess's dad visits with his new fiancée, who went to high school with Jess. A suspicious Jess attempts to ruin their relationship. Meanwhile, Schmidt is trying to land a sponge ad campaign and enlists the guys' help to disastrous results.
Nick hatches a bet with Jess that she's just as superficial as the rest of the guys when it comes to dating. Meanwhile, Winston and Cece team up to trick Schmidt and Coach into thinking they're going to be models.
When Coach's liaison with the school nurse gets messy, vice principal Jess must enforce a new, "no fraternization" policy among the teachers. But the tables soon get turned when she finds herself attracted to the hot new science teacher. Meanwhile, Nick is enjoying being Schmidt and Winston's secretary, after the loft gets a new home phone.
Jess admits she might be in possession of certain illegal substances, which complicates Winston's plans as the loft must pass a home visit and a background check as a part of his police academy training.
Nick pretends to be gay so that Jess's new boyfriend will feel less threatened. Coach is annoyed at Winston for working his "Long Game" on two attractive neighbors. Meanwhile, Schmidt is bummed to learn Cece is considering having her breasts reduced.
Schmidt quickly regrets trying to understand the politics of a girl fight when one breaks out between Jess and Cece. Meanwhile, Nick goes on a date with Tran's granddaughter, whom Winston believes is hiding a secret.
The gang go out on a bar crawl for Valentines to help nick with his breakup. Winston is the only one who is truly supportive and CeCe tries to out drink Nick. Ryan asks Jess an important question to which she pretends not to hear then finally accepts. Coach meets a woman several times before deciding to go after her. Ryan is offered a job back in England and Jess decides to make it work. The gang finish the bar crawl.
Jess crashes a funeral, hoping to delete a "sext" she recently sent to the deceased. Then, Schmidt's mom, Louise arrives in town for a visit, and Winston is desperate to be off-duty friends with his police partner, Aly.
Fawn takes Jess to a charity golf tournament, but the Vice Principal lands in the sand trap in her attempts to make a good impression. Meanwhile, Winston meets a beautiful woman and must lie about being a cop.