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.