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

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.

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.

When Nick's con-man father suddenly reappears, Jess tries her best to fix the two men's relationship, despite Nick's fears that he's being used in another one of his dad's gambling schemes. Meanwhile, Schmidt teams up with Robby to try to win back Cece.

When a death occurs in Nick's family, Jess, Schmidt and Winston travel with Nick to the Windy City to help him with the funeral preparations and meet his boisterous family members, including his mom, Bonnie; his younger brother, Jamie; and his Boston cousin, Bobby.

Cece's wedding day finds Jess and Nick making a decision about their relationship. Meanwhile, Schmidt schemes with a typically overenthusiastic Winston to sabotage the nuptials, although a shocking announcement may be bigger than anything he plans.