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Jess is ready to paint the town purple when a chance encounter finds her and best friend Cece invited to a once-in-a-lifetime mansion party thrown by music legend Prince. Not wanting to miss out on the fun, Nick, Schmidt, Winston and Coach are determined to crash the festivities, building toward an Unforgettable ending.
Nick struggles to throw Jess the perfect birthday party, while Schmidt works overtime to help out Cece in her new job as bartender and Winston and Coach engage in a bake-off.
Jess tries to become good friends with Coach by watching Detroit Pistons games with him and becoming a Pistons “fan”. However Jess’ “fandom” starts to interfere with her relationship with Nick, who is a lifelong Chicago Bulls fan. Winston agrees to shadow Schmidt at his marketing job, where Schmidt is later asked to guide Ed (Bob Gunton), a sixty-something intern, to avoid a company lawsuit over age discrimination.
When Jess has to make a quick decision about her career, her friends all recall how they ended up at their jobs.
Nick and Jess take the gang camping for Thanksgiving; Coach and Schmidt compete to prove who is the best woodsman; Cece and Winston bond over a shared dislike for the outdoors.
Jess must occupy Schmidt while Cece goes on a date with Coach; Nick and Winston search for Ferguson.
An overabundance of Chinese food take-out menus left at the loft’s front door is the catalyst for an interconnected series of adventures for Jess and the guys.
Coach visits the apartment to spend a “guys night out” with the guys, after breaking up with his girlfriend. Nick going to a strip club with the guys, and telling her that they haven’t had a conversation about whether or not they’re boyfriend/girlfriend or are exclusive, upsets Jess to the point that she has “girls night out” with Cece at the bar.
Schmidt receives a series of recent e-mails from his favorite actor Michael Keaton, who has sent letters to Nick ever since he was a kid. However, it turns out those letters and e-mails were not from the actor but from Schmidt’s mother and Nick, posing as Keaton. Cece indulges in nightly parties to get over her break up with Schmidt.
Nick becomes irresponsible with the money from his late father’s estate, so Jess uses some of the money to pay Nick’s unpaid bills, behind his back. With Nick’s improved financial situation, Winston feels its finally time to ask Nick for the money he owes him.
Schmidt sets out to sabotage Jess and Nick’s relationship.
Thinking Schmidt has chosen to be with Cece, Jess and Nick invite him to go on a double date with them. Nick is caught between loyalty to his friend and loyalty to his girlfriend when he finds out a shocking secret. Meanwhile, Winston promises to get the foursome a table at an ultra-exclusive restaurant that doesn’t take reservations.
Jess has been hired at a new school and is eager to prove herself as one of the cool teachers.
Nick and Jess make a romantic run for the border — but their wild Mexican adventure takes a turn for the worse when Nick is arrested.
Cece’s wedding day finds Jess and Nick making a decision about their relationship. Meanwhile, Schmidt schemes with a typically overenthusiastic Winston to sabotage the nuptials, although a shocking announcement may be bigger than anything he plans.
Jess’ dad chooses the worst day to pay the loft an unexpected visit, forcing a nervous Nick to spend the day alone with him. Jess finds herself with huge opportunity for a new job on the day before Cece’s wedding. Schmidt must take a look in the mirror and confront his real feelings about Elizabeth. Meanwhile, Winston psyches himself up for his huge surprise birthday celebration, which no one seemed to remember to throw for him.
In a series of flashbacks, Jess, Nick, Schmidt, Winston and Cece tell one another how they each lost their virginity. Not surprisingly, when they realize the stories directly affect their present day sex lives, one relationship will change forever.
Jess decides to throw Cece a surprise bachelorette party while Nick and Winston awkwardly take her fiancé, Shivrang, out for the night. Then, as Schmidt desperately tries to find a real girlfriend in time for the wedding in order to get a “plus one,” he is forced to seek out his old girlfriend from his “fat Schmidt” college days.
Jess and Nick, who are caught between friendship and something more, try to break out of relationship-limbo by going on a First Date. Once Schmidt and Winston realize a full-on Jess/Nick romance might be happening, they swoop in to try to sabotage the date.
When a death occurs in Nick’s family, Jess, Schmidt and Winston travel with Nick to the Windy City to help him with the funeral preparations and meet his boisterous family members, including his mom, Bonnie; his younger brother, Jamie; and his Boston cousin, Bobby.
Jess comes to a conclusion about her romantic feelings for Nick and she struggles to tell him – until she’s hopped up on pain medication. But after admitting her feelings, she finds out he may have been keeping something from her. Meanwhile, Schmidt becomes obsessed with buying a fish, which Winston sees as a metaphor for Schmidt’s unresolved feelings toward Cece and Nick plans a bar promotion to impress the bar owner (guest star Odette Annable).
Jess catches the eye of a professional football player, with whom Winston landed an exclusive interview for his radio station. Meanwhile, Nick and Schmidt argue over the planning of their “TinFinity” party celebrating their tenth anniversary of living together, and Cece gets a surprise offer
When Schmidt discovers a previously unknown, yet highly-coveted parking spot, Jess and the roommates battle it out to see who will get to use it. Meanwhile, Winston has a hard time finding a condom when he gets an impromptu invitation from Daisy.
The gang attends a dating convention, where Cece hopes to find a prospective husband – even as Schmidt hopes to win her back. Meanwhile, Winston’s mojo returns, and Jess and Nick get put in a compromising position in front of Dr. Sam.
Nick and Schmidt go out on a “bro’s night,” but quickly become infatuated with, and highly competitive over, a beautiful woman attracted to sadness. Meanwhile, Winston falls for a girl with absolutely no interest in him, which only makes him more attracted to her. Then, Jess’ decision to have a night alone in the loft doesn’t go as planned and involves another round of the drinking game “True American,” and a surprising development in her relationship with one of the loft mates.
Nick becomes convinced that a promising student in Jess’s adult writing class is a murderer.
When Nick’s con-man father suddenly reappears, Jess tries her best to fix the two men’s relationship, despite Nick’s fears that he’s being used in another one of his dad’s gambling schemes. Meanwhile, Schmidt teams up with Robby to try to win back Cece.
Jess and Sam go on a weekend getaway with Nick and Angie. But this might not be the trip they expected when Jess starts to party and trouble begins. Could jealousy get in the way of a good time?
When the gang attempts to juggle multiple holiday parties in one night, Jess tries to avoid a remorseful Sam, Nick tries to keep up with a sexually adventurous Angie and Winston panics when he gets a cranberry stuck in his ear.
Tired of taking showers, Jess and Winston scheme to get a bathtub in the loft. Then, at the bar, Nick meets a tough and beautiful customer with boyfriend troubles. Meanwhile, Schmidt is torn between his boss and trying to win back Cece.
When Jess learns that a friend is pregnant, both she and Cece panic that time is running out for them to have children. Meanwhile, Schmidt seeks advice on how to please Emma, and Nick and Winston visit the zoo to find inspiration for Nick’s zombie-themed novel.
Jess invites her divorced Mom and Dad over for Thanksgiving dinner and enlists Nick and Cece to help her with a “Parent Trap” to reunite them. Meanwhile, Schmidt’s cousin, Big Schmidt, visits, and Winston manipulates them into an escalating battle to prove their manhood.
As Jess’ job search kicks into high gear, the guys fear her time of the month is also affecting their physical and psychological well-being. Meanwhile, Schmidt begins a “50 Shades of Grey”-type of relationship with his corporate boss, and Nick gains wisdom from an unlikely, hands-on (and mute) source.
Jess gets a job as a zombie at a haunted house, but is more frightened of her changing feelings towards Sam. Schmidt and Cece are perfectly matched in the costumes they’re wearing, while Winston and Shelby are worlds apart in theirs. Nick gets a visit from a former college crush who shows her affection in a scary way.
After spending a wild night out with Cece and her model friends, Jess jumps in the driver’s seat when she must fill in for Cece at a car show. Meanwhile, the guys question what defines male friendship after Schmidt buys Nick a cookie.
Jess gets a quartet of very young new neighbors — and she’s determined to win them over, in spite of the fact that to them, she’s not a New Girl — she’s an Old Girl
Jess and Nick examine their friendship. Elsewhere, Schmidt hopes to impress an attractive Republican by pretending to be one of Mitt Romney’s sons.
Jess pretends she’s someone else when a handsome stranger mistakes her for his blind date. Meanwhile, a patron at Nick’s bar claims to be Nick from the future, and Winston’s disapproving mother pays him a visit.
Jess is laid off from her teaching job and volunteers to be a shot girl at Schmidt’s “rebranding” party.
When one of the roommates decides to move out of the loft, the gang makes an unexpected trip to the desert where Winston faces his fear of the dark, Cece and Schmidt’s relationship reaches a turning point and Jess and Nick square off with a coyote.