Nick and Schmidt convince Jess to get her stuff out of her ex-boyfriend Spencer's apartment; Jess meets new roommate Winston, who has returned from playing basketball in Latvia. Winston tries to get his old room back from Schmidt.
The guys are invited to a wedding, and Nick is fearful that he'll run into his ex, so he asks Jess to be his date. Meanwhile, Winston takes his role as usher very seriously, and Schmidt catches the eye of two women.
Jess accidentally walks in on Nick naked, sending his self-confidence to an all-time low - just after an attractive co-worker agrees to go out on a date with him. Meanwhile, Winston becomes obsessed with learning pop-culture references online.
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.
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.
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' baby shower to compete with his office female counterpart.
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 wonders who placed a 50 dollar bill in the douchebag jar.
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.
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.
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.
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.
When Nick is hurt playing a game of touch football and Jess discovers he doesn't have insurance, she takes him to her doctor friend -- an OB-GYN. The gang rallies together and Nick evaluates his life when his seemingly innocuous back injury may prove to be more serious than thought.
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.
Jess reluctantly dates the wealthy father of one of her students. Meanwhile, Nick attempts to buy a new cell phone and Schmidt and Winston get ultra-competitive playing bar trivia.
Jess' sophisticated date with Russell doesn't go as planned. Meanwhile, Nick's college friend visits and brings out Nick's inner frat boy to help him get over his break-up with Julia. Also, Winston panics when Shelby goes on a "girls" vacation and Schmidt and Cece try to keep their relationship under the covers, but one of the friends finds out their secret.
While training for a marathon, Jess discovers that Cece has been keeping a secret from her, and their friendship is put to the test. Meanwhile, Winston can't handle being the only one who knows about Cece and Schmidt, and Nick reluctantly asks for Schmidt's help as he tries to juggle dating two women at once.
A nervous Jess invites Russell to spend the weekend at the loft, and her fears are amplified when he gets along better with the guys than she hoped. Meanwhile, Winston begins work at a sports radio station, but quickly finds out his boss is more of a shock jock, and Nick tries to make an invention from his "Idea Notebook" into a reality.
Jess babysits Russell's pre-teen daughter for the weekend and meets his ex-wife. Then, Schmidt and Cece panic when they think she's pregnant. Also, Nick's new girlfriend may be too young and Winston discovers his new boss is a big baby.
Jess fears she and Russell don't share the fiery passion he exhibits with his ex-wife Ouli. Meanwhile, Cece is not yet willing to admit her true feelings for Schmidt, so she encourages him to go on a date with one of her Russian model roommates. Then, a down-in-the-dumps Nick channels all of his energy into a new vegetable garden.
When Jess and Nick run into their exes Paul and Caroline, the gang fears they both may "backslide" into romantic relationships. Meanwhile, Schmidt desperately tries not to get aroused as he deals with a delicate medical issue, Winston suffers the consequences of a wild night out with his boss and Cece brings Schmidt to a nursing home to meet her grandmother.
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.