After a breakup with her cheating boyfriend, teacher Jess Day moves in with three men; a personal trainer, a bartender, and a ladies man.
Schmidt and Nick help Jess move out of her ex-boyfriend's apartment. Afterwards, she meets their new roommate, Winston.
Nick asks Jess to be his date at a wedding in fear of running into his ex there.
Nick's self confidence is seriously shaken when Jess walks in on him naked.
Cece stays over and tells Jess she believes that Nick's feelings for her are more than platonic.
Jess invites a music teacher she's always harbored a crush on, Paul, to their apartment's big thanksgiving dinner.
Winston joins Jess's troubled youth handbell quartet and she gets jealous when he's instantly gifted. Meanwhile, Nick and Schmidt compete on fixing the toilet.
Jess takes sex advice from her roommates when she and Paul move further in their relationship.
The group attends Schmidt's office party for the holidays. Meanwhile, Paul gives Jess a fancy gift.
Jess and her school's vice-principal plan Schmidt's 29th birthday party.
Nick freaks out when Julia doesn't want to label their relationship. Meanwhile, Jess seeks Julia's help to get rid of a traffic ticket.
Jess goes against Nick's wishes and becomes obsessed with getting their landlord to like her, which puts their living situation at risk.
Jess convinces Schmidt to be her wingman and help her hook up with a handsome guy for Valentine's day.
When Jess tries to deal with a bully in her classroom, she finds herself a victim of the very same student.
Nick gets injured while playing touch football and Jess takes him to her friend, an OB-GYN, after she discovers that he has no health insurance.
Jess realizes that Schmidt unfairly does all of the household chores alone. Meanwhile, Nick owes Winston a large sum of money when he loses against him at poker.
Jess begrudgingly agrees to date the rich dad of one of her students. Meanwhile, Nick tries to buy a new cellphone.
Jess's dates with her student's father end awkwardly. Meanwhile, Nick is visited by his friend who helps him forget Julia.
Cece and Jess's friendship hits a rough patch when the former hides things from Jess.
Jess asks Russell to spend the night but is afraid of her roommates' reactions. Meanwhile, Winston gets a job at a radio station but it's not like what he'd imagined.
Jess babysits Russell's adolescent daughter and meets his ex-wife. Meanwhile, Schmidt and Cece have a pregnancy scare.
Cece refuses to admit her feelings for Schmidt, so she sets him up with her model roommate. However, she gets jealous when he does.
The group are afraid Nick and Jess may "backslide" into their old relationships when they meet their respective exes.
One of the group wants to move out, so they all decide to take a trip to the desert, where Winston is confronted with his fear of the dark.