9 Toxic: Nathan's sex tape
During his previous relationship with Peyton Sawyer, Nathan even slept with Peyton's best friend, Brooke Davis, and made a sex tape with her. This would have been bad enough if Nathan didn't go on to get married to Haley.
Why did Peyton and Nathan break up?
During their first two years of high school, Nathan, the basketball star, entered a romance with the lonely cheerleader, Peyton. ... Nathan showed little interest in Peyton and only liked her for sex. Eventually, Peyton had enough of Nathan and his behavior and ended their relationship.
What episode does Peyton find out Brooke slept with Nathan?
Prom Night at Hater High.