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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 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
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.
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.
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.
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.
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.
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.
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.
It’s Thanksgiving and Jess and the gang are determined to make this year’s festivities a success. However, things don’t go according to plan when Robby surprisingly shows up and Schmidt’s dad arrives heartbroken. Meanwhile, Nick finds out that Regan is postponing her move-in date and Winston deals with his “heroic” injury.
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.
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.
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).
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 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.
Jess tries anything and everything to get her mind off of Nick, who returns from his summer in New Orleans sooner than anticipated. Meanwhile, Schmidt and Cece struggle in the search for their first home and Winston deals with having a long-distance relationship with Aly.
Schmidt makes a last ditch effort to convince Cece’s mom to come to their wedding, but in doing so, he might miss the special day himself.
On the night before the wedding, Nick and Winston try to help Schmidt re-write his vows and Jess, thinking that Sam is going to propose to her, rallies the gang into playing True American to avoid giving him an answer.
Jess meets Sam’s female best friend, Diane. Meanwhile, Nick is worried Gavin will disappoint Schmidt again and Winston is offended by a reaction to a birthday gift.
Jess races to make alterations to Cece’s bridal dress, while Schmidt tries to keep his “wedding workshop” a secret at work, and Nick struggles to ask Reagan to be his date to the nuptials. Meanwhile, Winston and Aly try to keep their relationship on the down-low at work.
Refusing to accept that their crazy days are behind them, Jess and Cece abandon their low-key bachelorette party plans and seek a night out to top all others.
After being emasculated in front of Cece, Schmidt insists on a manly bachelor party weekend in Vegas, but the road trip goes awry when the guys end up at a desert biker bar and he must put his newfound bravado to the test.
Despite being happy with Sam, Jess confesses to Cece that she had a sex dream about Nick. And Schmidt attempts to help Winston land Furguson a cat audition when he finds out Aly’s boyfriend is a talent agent for pets.
Jess invents a male alter ego, “Jeff Day,” in order to buy a new car from a sexist salesman, but her plan backfires when both Nick and Sam arrive at the dealership pretending to be him. Meanwhile, Schmidt and Cece panic when Winston decides to bring his new prankster girlfriend, Rhonda as his plus one to their wedding.
When Jess is served a restraining order by her ex-boyfriend, Sam, she sets out to clear her name with Winstons help. Nick and Schmidt plot against the owner of a trendy new bar that opened on their street.
Jess applies for a job at a progressive new school, but things take a turn when she finds out the principal is dating her ex-boyfriend, Sam. Meanwhile, Nick gets a cold and Schmidt quarantines the roommates to prevent himself from getting sick before his big presentation.
After Cece receives an exciting new job offer, Jess agrees to help Schmidt with the wedding preparations, but things don’t go as planned when Schmidt’s dad, Gavin, appears. Meanwhile, Winston and Nick get into a competition over whose job is harder.
It’s time for Cece to move into the loft. While Jess is helping her friend move out of her beloved apartment, she has to finish the school’s budget by morning, which the new principal has neglected to tell her. Meanwhile, Winston gets a new partner to avoid having to work side-by-side with Aly.
Jess attempts to discover the real identity of a juror who was sequestered with her; Reagan prepares to move on; Winston and Cece help Schmidt overcome his fear of public dancing.
Things heat up between Nick and Reagan over who can provide the loft with the best air conditioning unit. Meanwhile, Winston uses his “cop voice” to help Schmidt prep Cece for a newscaster audition.
Reagan challenges Nick and Winston’s indecisiveness when she says she will sleep with only one of them; while looking at wedding venues with Cece, Schmidt runs into his college frenemy, Benjamin.
Schmidt and Cece take action when Nick’s attraction to Reagan impacts their relationship; Winston teaches Reagan about breakups.
A beautiful pharmaceutical rep enters the gang’s life when she agrees to sublet Jess’ room while she is on jury duty.
Nick’s cousin and his wife visit with a very special request, which prompts Schmidt to offer Nick a glimpse into the future. Meanwhile, Winston and Cece shop for a wedding dress.
With Jess sequestered at jury duty, Nick turns the loft into an airbnb in order to help pay for Schmidt’s upcoming bachelor party. Meanwhile, Winston asks Cece for help when he suspects KC is cheating on him.
Jess eagerly reports to jury duty, until she discovers she may be up for a work promotion. Meanwhile, Nick reaches his limit with Cece’s messiness in the loft.
Jumping back into the dating pool, Jess finds herself dating a dud (guest star Taran Killam), but falls in love with his perfect parents (guest stars Henry Winkler and Julie Haggerty). Meanwhile, Nick (Jake Johnson) and Schmidt have very different ideas about how to run the bar.
When Cece and Schmidt ask Jess and Nick to be their Maid of Honor and Best Man, respectively, their first task is to plan the engagement party. But when Jess invites Cece’s mom to join in the celebration, Cece is forced to make a surprising announcement to Schmidt.
As Coach prepares to move out of the loft, Schmidt also decides to get rid of his non-essentials and in the process discovers what is truly important to him; Jess and Nick reminisce about their “sex mug” and wonder if they still have feelings for each other.
Schmidt takes the fall to help Fawn out of a political scandal. Meanwhile, Jess declares herself a “love doctor” and Coach faces a life-changing decision with May.