Jess admits she might be in possession of certain illegal substances, which complicates Winston's plans as the loft must pass a home visit and a background check as a part of his police academy training.
Jess Day is a young woman who, after discovering her long-term boyfriend is cheating on her, moves into a loft apartment with three male roommates - prickly bartender Nick, womanizer Schmidt and intense personal trainer Coach. The guys try to help Jess get back on her feet and into the dating world.
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 of a mutual friend. Nick, fearful he will run into his ex-girlfriend Caroline, asks Jess to be his date. Meanwhile, Winston takes his role as an usher very seriously and gets competitive on the dance floor with a young guest. Schmidt not only catches the eye of a beautiful woman, but also his "frenemy" Gretchen whom he sleeps with at every wedding reception.
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 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 argues why one of them has to place 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 brings 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's first date with Russell ended with a pat on the back. The second date ends abruptly. He explains he is out of dating practice. Nick's friend visits and helps him get over Julia. Winston finds out about Schmidt & CeCe.
Winston shares the secret about Schmidt and CeCe with Nick, and Nick tells Jess. Jess is upset CeCe did not tell her when it started and it puts a strain on their friendship. Nick's dating younger women and asks Schmidt for help to handle it.
Jess invites Russell to stay overnight at her place and is worried about how the guys will react. Winston gets a job at a radio station but finds it is not what he thought it would be. Nick pitches one of his marketing ideas to Russell.
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.
CeCe does not want to admit she cares for Schmidt, so she tells him to date her gorgeous model roommate. He does, but then she gets jealous. Jess meets Russell's first wife and does not think she matches up to Ouli who seems so exciting.
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.