Jason Strider and his friends grapple with dating, sex, and surviving as adults. When a one night stand steals Jason's heart and his pants, he begins a quest to get his beloved jeans back!

Jason, egged on by his friends, posts an ad looking for Jane on missed connections. Tina loses her licence to mock him, when, while anxiously awaiting a text from Brett, she de-virginizes an intern.

Jason quits his job; networking at James Franco's party; Tina wonders if she is prepared to date Brett.

Jason and Tina decide to change their fortunes with a debauched night out. First, Tina must stop by Stacey's penis-themed sorority bachelorette party, whilst Jason is delayed by a needy drug dealer.

Tina has an embarrassing diagnosis; Jason finds work as a cleaning person and starts hooking up with the boss.

Jason still can't find a job and is getting desperate for cash; Tina has a job, but is also broke due to irresponsible purchases, i.e., high-waisted skinny jeans.