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 pretends she's someone else when a handsome stranger mistakes her for his blind date. Meanwhile, a patron at Nick's bar claims to be Nick from the future, and Winston's disapproving mother pays him a visit.

In a series of flashbacks, Jess, Nick, Schmidt, Winston and Cece tell one another how they each lost their virginity. Not surprisingly, when they realize the stories directly affect their present day sex lives, one relationship will change forever.

Nick and Jess make a romantic run for the border -- but their wild Mexican adventure takes a turn for the worse when Nick is arrested.

Jess is ready to tell Nick of her true feelings for him. Meanwhile, Nick takes a meeting with a book publisher, as Aly helps Winston reconnect with an important person. Then, Cece and Schmidt receive big news.