Jessica Day is an offbeat and adorable girl in her late 20s who, after a bad breakup, moves in with three single guys. Goofy, positive, vulnerable and honest to a fault, Jess has faith in people, even when she shouldn't. Although she's dorky and awkward, she's comfortable in her own skin. More prone to friendships with women, she's not used to hanging with the boys--especially at home.
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.
The gang attends a dating convention, where Cece hopes to find a prospective husband - even as Schmidt hopes to win her back. Meanwhile, Winston's mojo returns, and Jess and Nick get put in a compromising position in front of Dr. Sam.
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 Nick is convinced that one of Jess' students is hiding a nefarious secret, he goes undercover in her adult night school class. Meanwhile, Winston has an embarrassing encounter with Cece, causing an examination of all the loft-mate's peculiarities.