Jess and Cece jump on the campaign trail and make a bet with a disbelieving Schmidt that they can recruit voters for the upcoming Presidential election. Meanwhile, Winston teaches Nick about modern phone sex.

When Schmidt and Cece and Winston and Aly invite Jess on their couples glamping trip, members of her singles-only group tag along. Meanwhile, Nick struggles with the next chapter of his New Orleans-set novel after Schmidt gives him "no notes".

Jess and the gang head to New York, where Schmidt believes he is being honored at his high school. Jess meets Det. Jake Peralta and helps him on a case, which leads her to Brooklyn’s 99th Precinct and a fateful encounter with Gina Linetti and Capt. Raymond Holt. Meanwhile, Nick and Winston scramble to make subway fare, while trying to impress Det. Charles Boyle, and Cece faces off with her new mother-in-law. The crossover starts on Brooklyn Nine-Nine S04E04 The Night Shift (I).

While the gang helps Schmidt & Cece remodel their fixer-upper, Jess spearheads a vote to let Reagan eventually move back into the loft. Meanwhile, Nick and Winston make a revealing discovery and Schmidt and Cece learn the art of compromise.

After Jess announces that she is ready to date again, Schmidt pushes her to give her workout partner, Robby, a fighting chance. Then, when Cece hires a hunky new bartender, Nick struggles to understand male beauty, while Winston's newfound confidence makes him irresistible.

In order to land the soon-to-be open principal's position at her school, Jess must impress the disapproving president of the Parents' Council. Winston puts his undercover skills to the test and Nick struggles to come up with the perfect wedding gift for Schmidt and Cece.

Schmidt enlists Nick to help him earn the respect of his difficult house contractor. Meanwhile, as Jess and Robby test the limits of their ability to be in a casual relationship, Winston and Cece debate the pros and cons of not being single.

Jess struggles to keep the loft's Secret Santa gift exchange afloat. When Winston believes his online gift order for Cece won't be delivered in time, he and Schmidt must endure going to an actual store to find a replacement gift. Meanwhile, Reagan surprises Nick, who helps makes Jess' Christmas one to remember.

When Reagan moves into the loft, Nick tries to "play it cool." Meanwhile, Schmidt embarks on a soul-searching journey when Cece and Winston challenge his love of electronic dance music.

When Jess insists on covering Robby's medical bill, she is stunned after finding out the total and goes to extremes to find a way to help pay. With Schmidt and Winston's help, Cece attempts to get her new modeling agency off the ground (and out of the loft), but is discouraged when her first client is inspired to change career paths. Meanwhile, Reagan puts off reading Nick's new novel.

As Jess tries to find a new vice principal, she discovers that she has a real problem when it comes to making decisions. Meanwhile, Cece enlists Jess and Reagan to help her recruit new models, and the guys are in for a surprise when they enjoy a day at the spa.

While on a day hike, Jess and Robby discover something unexpected about their relationship. Also, Winston throws a surprise welcome home party for Aly. Meanwhile, Schmidt and Cece fail to impress their new neighbors.

When Nick freaks out after Reagan lands him a book signing, Jess scrambles to boost his confidence and help it go smoothly. Meanwhile, Winston reveals to Schmidt and Cece that he's proposing to Aly, but needs their help to execute the big plan

On Valentine's Day, Jess tries to convince the gang that she is perfectly content being single. Meanwhile, Schmidt competes for a big promotion and Winston's proposal plans to Aly are expedited.

When Jess gets nervous about starting her new position as principal, Nick and Schmidt decide to take her on a relaxing day trip to Solvang, which quickly goes "sideways." Meanwhile, with Cece's help, Winston tries to finalize his divorce from Rhonda, but finds that he and Aly are caught in a series of never-ending pranks.

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.

When Reagan returns home from a work trip, Jess is concerned that she has been spending too much time being Nick's "girlfriend." Meanwhile, Schmidt and Cece obsess over security in their new home and Aly reveals an embarrassing secret to Winston.

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.

As Jess continues to stay with her dad in Portland, they unexpectedly help one another with their love lives. Meanwhile, Nick turns to a reluctant Aly for help with his relationship with Reagan, and Schmidt contemplates using his first name.

Jess is ready to tell Nick of her true feelings for him. Meanwhile, Nick takes a meeting with a book publisher, as Aly helps Winston reconnect with an important person. Then, Cece and Schmidt receive big news.