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 .