Set in 1988, the film begins in a music store with recent MIT graduate Matt Franklin (Topher Grace), his twin sister Wendy (Anna Faris), and his best friend Barry Nathan (Dan Fogler) as they try to figure out when to see Matt's dream girl Tori Fredreking (Teresa Palmer). Following graduation, Matt has been working at a Suncoast Video store while trying to figure out what to do with his life. While working one day, Tori randomly walks into the store. When she asks him where he works, he lies and tells her he's at Goldman Sachs. Tori then invites him to a Labor Day weekend party held by Wendy's boyfriend Kyle Masterson (Chris Pratt). Matt, Barry and Wendy drive to the party later that night, but before they arrive, Barry steals a car from the dealership where he got fired from earlier in the day.
At the party, Kyle challenges people to ride the "ball," a hollow steel sphere that is supposed to ride down the street. Matt runs into Carlos (Demetri Martin), a high school classmate who actually works at Goldman Sachs. Barry tries the cocaine Matt found in the stolen car, and is involved in a dance battle, after which Kyle proposes to Wendy. Then Matt and Barry leave with Tori and her friends to a business party in Beverly Hills. On the drive to the party, Tori tells Matt that her boss, Peter (Michael Ian Black) hired her just to see her naked. At the party, Tori reveals to Matt that she hates her job. Matt and Tori leave the party, enter the backyard of a neighbor's home, and jump on a trampoline where they play truth or dare. When they get too far, Matt ends up sleeping with her. Then, Matt tells Tori the truth about his job, causing Tori to become upset and leave.
