Unable to handle the pressure from Dan, Nathan decides to quit the basketball team and looks to Haley to help him fill his free time. Meanwhile, Brooke becomes increasingly jealous of Lucas and Peyton's growing friendship.

Lucas must make a difficult decision regarding Brooke. Haley considers having sex with Nathan.

Felix organizes a "dare night" to test the limits of his new classmates. While out playing the game, Lucas meets a mysterious new girl, Anna, and the two of them seem to hit it off. Peyton tearfully confesses to the church that she recently tried cocaine and Keith is caught off guard when a beautiful woman comes to the shop and begins flirting with him. Meanwhile, Karen goes on a date with Andy, her younger professor.

Nathan's Uncle Cooper comes into town to take Nathan and Lucas on a racing trip. On the track, Nathan and Lucas are challenged to a race by the beautiful Daytona and her smart aleck brother Jarret, but things go horribly wrong when Nathan loses control of his car and crashes into a wall. Meanwhile, Deb's addiction to pain pills intensifies and Dan exposes Andy's relationship with Karen to his class.

In the first part of the two hour second season finale, things heat up between Lucas and Brooke after they head to New York for an overnight stay with Haley. Peyton is elated when she gets the band Jimmy Eat World to perform at TRIC in time for Jake's release from jail. Meanwhile, Andy invites Karen to spend the summer in New Zealand.

The Ravens begin basketball practice. New team captain Nathan clashes with Lucas over Haley, and a new cheerleader sets her sights on Lucas. Elsewhere, Dan's mayoral bid takes a surprising turn when an unlikely opponent emerges, Karen.

Haley argues about her wedding dress with Brooke during the rehearsal dinner. Elsewhere Karen and Lucas arrive back in town.

And Peyton is surprised by what she finds...

It's Prom night, but things start to go awry as Lucas discovers who was the person in the hallway when Keith was killed, and psycho Derek holds Peyton hostage at her own house. Meanwhile, Haley and Nathan vow to be romantic with each other throughout the night, and Dan continues to win over Karen's affections.

It's confrontation time in Tree Hill, as Lucas confronts Peyton about her nasty behavior towards Lindsey and Brooke must confront Victoria about meddling with Peyton's record label. Meanwhile, Nathan begins to grow closer to Carrie, Haley continues to struggle in dealing with Quentin, and Mouth must choose sides between his co-workers and Alice.