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.

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.

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.

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.

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.

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

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'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.

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.