Jess believes the time is right to let Nick know how she feels about him. Later, Nick meets with a book publisher; Aly helps Winston reunite with an important person; and Cece and Schmidt get big news.
While Jess is staying with her dad in Portland, the two are instrumental in helping one another with their love lives; Nick seeks Reagan-relationship help from a reluctant Aly; and Schmidt considers using his first name.
Jess runs away from her feelings for Nick by heading to Portland to take care of her dad. Meanwhile, at a work party with Reagan, Nick turns panicky when he realizes they really don't know each other. Aly steels herself for her introduction to Winston's mom and learns the woman hasn't been told they are cops.
Jess worries that Reagan, who's just returned from a business trip, is spending too much time as Nick's "girlfriend." Meanwhile, Schmidt and Cece worry about security in their new home; and Aly tells Winston an embarrassing secret.
Jess is concerned that she may not be a cool principal, so she recruits Nick and "The Pepperwood Chronicles" to give her a popularity bump among the students. Meanwhile, Schmidt hires a real go-getter as an assistant and Winston wonders if Furguson is two-timing him.
Nick and Schmidt plan a relaxing day trip for Jess, who is nervous about taking over as principal, but the outing takes a surprise turn. Meanwhile, Cece helps Winston try to finalize his divorce from Rhonda, but gets caught in the middle of a series of never-ending pranks involving him and Aly.
Decision-making appears to be a problem for Jess on her quest for a new vice principal; Cece recruits Jess and Reagan in her search for new models; and the guys get a surprise during an enjoyable day at a spa.
Jess insists on picking up the tab for Robby's medical bill, but she is shocked to learn the total; Schmidt and Winston help Cece get her new modeling agency off the ground (and out of the loft). Meanwhile, Reagan's in no hurry to read Nick's new novel.
Jess has problems keeping the loft's Secret Santa gift exchange going, while Winston worries his online gift order for Cece won't make it in time, so he and Schmidt are forced to go store shopping to find a replacement present. Later, Reagan surprises Nick, who helps give Jess an unforgettable Christmas.
Schmidt gets Nick to help him earn the respect of a troublesome house contractor; Jess and Robby test their ability to be in a casual relationship; and Winston and Cece argue the pros and cons of not being single.
Jess' efforts to land the soon-to-be-open principal's job require her to impress the difficult president of the Parents' Council. Meanwhile, Winston's undercover skills are tested; and Nick can't seem to find the perfect wedding gift for Schmidt and Cece.
Jess and the gang pull out all stops to guarantee their Thanksgiving festivities are a success, but things take an unexpected turn when Robby and a Schmidt's heartbroken dad show up. Meanwhile, Nick learns Regan is putting off her move-in date, and Winston deals with his "heroic" injury.
Jess decides she's ready to wade back into the dating pool, so Schmidt prods her to take the plunge with her workout partner. Meanwhile, Cece hires a hunky new bartender, leaving Nick to wrestle with the concept of male beauty; Winston's newfound confidence renders him irresistible.
The gang pitches in to help Schmidt and Cece remodel their fixer-upper, while Jess attempts to get out the vote to allow Reagan to eventually move back into the loft. Meanwhile, Nick and Winston make a surprising discovery, and Schmidt and Cece learn to practice the art of compromise.
In a crossover episode with "Brooklyn Nine-Nine," Jess and friends visit New York, where she meets that series' Det. Jake Peralta, helps out on a case and has an interesting encounter with two from the 99th Precinct. Meanwhile, Nick and Winston have trouble coming up with subway fare, and Cece squares off with her new mother-in-law.
Jess is invited to go with Schmidt and Cece and Winston and Aly on their couples' glamping camping excursion, and members of her singles-only group join them. Meanwhile, Nick has problems finishing the next chapter of his novel set in New Orleans.
Nick returns early from his summer in New Orleans, forcing Jess to do everything in her power to keep her mind off him. Meanwhile, Schmidt and Cece's quest to buy their first home is a tough sell; and Winston's long-distance relationship with Aly proves trying.