After leaving her long-time boyfriend, Jess moves into an apartment with three men, and tries to re-enter the dating world.

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

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.

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.

Jess applies for a job at a progressive new school, but things take a turn when she finds out the principal is dating her ex-boyfriend, Sam. Meanwhile, Nick gets a cold and Schmidt quarantines the roommates to prevent himself from getting sick before his big presentation.

Jess races to make alterations to Cece’s bridal dress, while Schmidt tries to keep his “wedding workshop” a secret at work, and Nick struggles to ask Reagan to be his date to the nuptials. Meanwhile, Winston and Aly try to keep their relationship on the down-low at work.

When Jess insists on covering Robby's medical bill, she is stunned after finding out the total and goes to extremes to find a way to help pay. With Schmidt and Winston's help, Cece attempts to get her new modeling agency off the ground (and out of the loft), but is discouraged when her first client is inspired to change career paths. Meanwhile, Reagan puts off reading Nick's new novel.

On Valentine's Day, Jess tries to convince the gang that she is perfectly content being single. Meanwhile, Schmidt competes for a big promotion and Winston's proposal plans to Aly are expedited.

Jess tries to appease Winston's anxiety about his impending fatherhood by tracking down his long lost dad. Meanwhile, Schmidt goes back to work for the first time since Ruth's birth.