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.

Jess tries to become good friends with Coach by watching Detroit Pistons games with him and becoming a Pistons "fan". However Jess' "fandom" starts to interfere with her relationship with Nick, who is a lifelong Chicago Bulls fan. Winston agrees to shadow Schmidt at his marketing job, where Schmidt is later asked to guide Ed (Bob Gunton), a sixty-something intern, to avoid a company lawsuit over age discrimination.

Jess fears someone is trying to sabotage her first middle school dance and she enlists the gang to help her chaperone on the big night.

As part of Winston's police academy training, the loft must pass a home visit and background check, which shouldn't be a problem until Jess admits she might be hiding illegal substances in her closet.