The show begins with Seth and Ryan discussing their fears of beginning school and seeing Marissa and Summer. When they first encounter their ex flames, Marissa is excited to see Ryan, but Summer walks away from Seth and then tells him she has a boyfriend. Meanwhile, Jimmy emerges from the yacht that he and Hailey have shared all summer and she quickly ends the conversation she was having on the phone.
Marissa stops home during school to get her car and makes out with the "yard guy," DJ. They talk as though they've been hooking up all summer. Seth's luck doesn't get any better, as he discovers that Zack, the new, cool edition to the comic book club is dating Summer. Caleb can relate to the pain of these teenagers because he gets drunk and Sandy takes him home to Julie. When Julie learns of Caleb's impending arrest, she threatens to take down Kirsten, too, unless Sandy helps.
Hailey reveals her secret to Jimmy: she has a chance to work in fashion and move to Japan. He responds by proposing, but she leaves and he is left to wonder what to do with his life. Ryan's life also takes a downward turn, as he catches Marissa kissing DJ. At the kickoff party, he tells Marissa that he does not want to be with her, either romantically or as friends. Seth's attempt at an apology does not go any better, as Summer dismisses him as "selfish." The one bright spot for Ryan is that his guidance counselor sets up his schedule in order to plan on a career as an architect.
The episode ends with Caleb being taken away in handcuffs. Sandy volunteers to be his lawyer.
"The Way We Were" File: