Nick and Schmidt go out on a "bro's night," but quickly become infatuated with, and highly competitive over, a beautiful woman attracted to sadness. Meanwhile, Winston falls for a girl with absolutely no interest in him, which only makes him more attracted to her. Then, Jess' decision to have a night alone in the loft doesn't go as planned and involves another round of the drinking game "True American," and a surprising development in her relationship with one of the loft mates.

When Schmidt discovers a previously unknown, yet highly-coveted parking spot, Jess and the roommates battle it out to see who will get to use it. Meanwhile, Winston has a hard time finding a condom when he gets an impromptu invitation from Daisy.

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.

Jess has been hired at a new school and is eager to prove herself as one of the cool teachers.