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.

After Dare Night resulted in new arrangements, a midnight meteor shower finds Lucas sharing a romantic night with Anna. Andy surprises Karen with a dinner and Keith cooks for Jules on their first date. Brooke finds herself forming a mutually beneficial relationship with Felix, and Peyton sets out to find an opening act for her club.

The opening of Karen's club "Tric" brings together the people of Tree Hill. Lucas and Felix come to blows over Anna. After Chris quits his gig the night of the club opening, Haley must face her fear of performing to save the night for Peyton. Although Mouth tends to Brooke while she is drunk, Felix sneaks in and attempts to take the credit. Keith and Jules realize their relationship has reached a new level, while Dan deliberately tells Karen that Deb slept with Keith.

The girls of Tree Hill have a slumber party, at which time secrets are revealed and bonds are made. Meanwhile, Nathan and Lucas road trip to Charlotte for a basketball game, and unknowingly to Lucas, they embark upon free HCM tests, a genetic heart condition that Dan maintains. Karen and Andy have a row.

Nathan is concerned about Lucas' health, so he tells Karen that Lucas didn't take the heart test. Dan offers Keith to continue working at the dealership-as vice president. At school, Peyton must confront the rumors going around that she is a lesbian. This affects her friendship with Anna. As for Nathan and Haley, they begin to grow apart...

Haley is surprised when her older sister Taylor comes to town, but not as shocked as Nathan, who recognizes Taylor from a past tryst. Brooke and Felix decide to become boyfriend and girlfriend. Jake makes a special visit to Peyton. Anna tells a secret to Lucas.

Nathan comes clean with Haley about his past relationship with Taylor, although Haley continues to email Chris without telling Nathan and Taylor finds out. Lucas and Karen remain at odds over his refusal to take the HCM test. Keith proposes to Jules. Meanwhile, Brooke fights for better working conditions at her new job. Lucas decides to take the HCM test.

As his marriage with Haley continues to go wrong, Nathan goes into a emotional crisis and becomes the "bad" Nathan of the past. Karen continues to struggle and try to figure out what would cause Lucas to move in with Dan. Peyton and Jake's relationship gets greater.

When Tree Hill High does a time capsule project, the gang confesses their most intimate secrets to an anonymous video camera. Nathan's anger over Haley's absence continues to grow, landing both Lucas and Nathan in jail. Peyton and Jake's feelings for each other heat up, while Felix throws Brooke a party to celebrate her new gig as student body president. Meanwhile, when brought to court, Lucas opts to live with Dan and Deb rather than Karen.

Keith and Jules' wedding day, and the event has turned the town upside down. Brooke asks Lucas to take her to the wedding as his date, Nathan makes an important decision involving his marriage to Haley, and Jake and Peyton take a big step in their relationship. Meanwhile, Karen and Andy discover Jules' secret relationship with Dan.