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 catches the eye of a professional football player, with whom Winston landed an exclusive interview for his radio station. Meanwhile, Nick and Schmidt argue over the planning of their "TinFinity" party celebrating their tenth anniversary of living together, and Cece gets a surprise offer

Jess decides to throw Cece a surprise bachelorette party while Nick and Winston awkwardly take her fiancé, Shivrang, out for the night. Then, as Schmidt desperately tries to find a real girlfriend in time for the wedding in order to get a “plus one,” he is forced to seek out his old girlfriend from his “fat Schmidt” college days.

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' dad chooses the worst day to pay the loft an unexpected visit, forcing a nervous Nick to spend the day alone with him. Jess finds herself with huge opportunity for a new job on the day before Cece's wedding. Schmidt must take a look in the mirror and confront his real feelings about Elizabeth. Meanwhile, Winston psyches himself up for his huge surprise birthday celebration, which no one seemed to remember to throw for him.

Cece's wedding day finds Jess and Nick making a decision about their relationship. Meanwhile, Schmidt schemes with a typically overenthusiastic Winston to sabotage the nuptials, although a shocking announcement may be bigger than anything he plans.