Nick and Schmidt go out on a "bro's night," but quickly become infatuated with and highly competitive over a beautiful woman (guest star Decker) 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.