16. The First Cut is the Deepest

Complete story — includes the ending

Nathan must decide which parent to live with after the divorce, but Dan decides to force his hand by threatening to reveal Deb's darkest secrets in court unless Nathan chooses him. Dan also attempts to bribe Nathan, which only angers him. Brooke is refusing to talk to Peyton or Lucas, declaring she doesn't want to ever talk to either of them again. Lucas, feeling upset at his recent breakups, sneaks out and meets a beautiful stranger in a bar, while trying to drink his frustrations with his shoulder away. He and the girl, Nicky, sneak out to a closed mall and have sex but she later disappears. Dan offers to buy Keith's garage and let him buy it back from him in time, and he begrudgingly takes the offer. Elsewhere, Peyton babysits for Jake. Lucas realizes he's becoming a person he doesn't recognize and vows to make things better. Deb confesses to Nathan that she left Dan for another man many summers ago and chose to leave Nathan with Dan. Nathan is heartbroken as she chose to leave him miserable with Dan and that impacted his whole life. Lucas apologizes to Brooke, who wants nothing to do with him. Nathan decides to emancipate from his parents. Sheryl Crow appears as herself and performs the song "The First Cut Is The Deepest" in Karen's Cafe. Nicky is revealed to be Jenny's mom. This episode is named after a song by Sheryl Crow.