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After a bad break-up, Jess, an offbeat young woman, moves into an apartment loft with three single men. Although they find her behavior very unusual, the men support her - most of the time.

After breaking up with her two-timing boyfriend, schoolteacher Jess Day moves in with three single males: a bartender, a womanizer, and a personal trainer.

When Schmidt's plans for his 29th birthday fall apart, Jess takes charge and enlists the help of her school's party hungry vice-principal. Meanwhile, Nick begrudgingly has his first date at Schmidt's party with a beautiful lawyer who harbors a secret, and the gang argues why one of them has to place a 50 dollar bill in the douchebag jar.

Against Nick's wishes, Jess makes it her mission to get the loft's cantankerous landlord to like her. In doing so, she inadvertently jeopardizes their living situation and the guys are forced to admit they've made some "unofficial" changes to the apartment. Meanwhile Schmidt tries to decipher what he thinks are mixed signals from his Boss Kim.

Nick panics when Julia doesn't want to put a label on their relationship. Meanwhile, Jess enlists Julia to help her get out of a traffic ticket, Winston reconnects with a former booty call and Schmidt is baffled as to why his shower towel is always damp.

Single for the first time on Valentine's Day, Jess convinces Schmidt to be her wingman as she attempts to have an attachment-free fling with a handsome stranger. Nick's romantic plans are foiled when he finds himself spending more time with Julia's law firm assistant than with her. Winston becomes one of the girls when Shelby invites him over on the holiday.

Nick and Schmidt help Jess get her things out of her ex's apartment. Later, Jess meets new roomie Winston, who's back from playing basketball abroad.

Fearful that he'll run into his ex-girlfriend at a wedding, Nick asks Jess to be his date. Meanwhile, Winston takes his role as an usher seriously.

Cece crashes at the loft after a bad breakup, and convinces Jess that Nick likes her more than just as a roommate.

Jess gets jealous when Winston joins her troubled-youth handbell quartet and instantly becomes a natural. Meanwhile Nick and Schmidt engage in class warfare when the toilet breaks and they each have their own idea of how to get it fixed.

Jess invites Paul, a music teacher at her school on whom she always has had a crush, to the gang's big Thanksgiving dinner at the loft, which naturally goes horribly awry.

When Jess decides to take her relationship with Paul to the next level, she consults with the guys for some sex advice. Meanwhile, Schmidt worms his way into his Boss 's baby shower to compete with his office female counterpart.

When Jess walks in on Nick naked, his confidence is sent to an all-time low, just after a pretty co-worker agrees to go out with him.

The gang attends Schmidt's holiday office party and Jess frets when she receives an expensive gift from Paul.

After Jess realizes that Schmidt is unfairly doing all of the housework, she pushes him to "go on strike," and the entire ecosystem of the loft is thrown off balance. Meanwhile, Nick scrambles when he must pay up to Winston after losing a poker game.

When Jess tries to intervene with a classroom bully she finds herself the target of the bad seed student. Schmidt, meanwhile, is thrilled over his post-Valentine's sexcapades, but hates that his paramour wants to keep it a secret; and Nick goes into a tailspin when Julia sends him a cactus.

Jess is laid off from her teaching job and volunteers to be a shot girl at Schmidt's "rebranding" party.

Out of work, Jess continues zany pursuits such as felt art and cooking unusual dishes. At the bar, a guy mistakes Jess for the blind date he is to meet. They have great sex and she continues to pretend she is Katie. Winston's mother visits.

Schmidt struggles to fit in when Jess befriends a group of 20 year olds who move in across the hall. Nick plays pranks on Schmidt to make him think he is old.

Jess continues to have great sex with Sam but does not date. Jess feels uncomfortable with a sex only relationship. Nick unwittingly becomes her surrogate boyfriend. Schmidt pretends to be one of Mitt Romney's sons to impress women.

Instead of celebrating Cece's birthday watching a movie, Cece wants to go out. Jess joins the models at a wild party at the bar. The next day, Cece is not able to model at a car show, so Jess steps in at the last minute. It does not go well.

When Jess's parents, Bob and Joan, show up at the same time for Thanksgiving dinner, Jess takes the opportunity to "parent trap" them into a reconciliation, but her ploy backfires. Meanwhile, Schmidt and his bigger ex-Marine cousin, Big Schmidt, engage in a "manliness" competition.

Nick prepares for a visit from Amelia, someone he had a crush on at college. Jess has a job at a haunted house for Halloween. She invites Sam, her non-boyfriend to the haunted house and plans to tell him she wants to be a girlfriend.

Unable to pay her share of rent and utilities, the guys tell Jess to get a job. She is experiencing her monthly period and is an emotional mess. Nick meets a silent guy who shows him how to be peaceful. Cece wants to get back together with Schmidt.

When Sadie tells Jess and Cece they only have so many eggs available for having children, Jess is worried and insists she and Cece get tests done. Schmidt tries to find confirmation for his sexual prowess. Nick finishes writing his book.