Season five is set four years into the future from the season 4 finale, and after the main characters have graduated from college.Production for this season of One Tree Hill, along with production for all other American scripted television shows, was caught in the middle of a contract dispute between the Writers Guild of America, East (WGAE), Writers Guild of America, west (WGAw) and the Alliance of Motion Picture and Television Producers (AMPTP).Carrie kidnaps Jamie, but Dan steps in to intervene.
Brooke sets Mouth on a blind date with her assistant Millicent, and finds out about Mouth and his boss. Haley is upset at Lucas for proposing to Lindsay and kissing Peyton.
After kissing Peyton, Lucas asks Lindsey to marry him. The Honorary Title performs at Tric, and Mia performs her song, "No Good". Quentin has to change his negative approach before the Ravens start the season-opening game.
Dan is released from jail and is hoping for forgiveness.
Deb becomes Jamie's nanny after the previous one kidnapped him, tried to steal Nathan, and tried to kill Haley.
Lucas has a new girlfriend, Lindsey, and a best-selling book.
Brooke's fashion line has taken off, but she still feels like her life is missing something. Nathan is in a wheelchair after a bar accident, and has to deal with recuperating and a future that possibly has no basketball in it. A., and she returns to Tree Hill still mourning the end of her relationship with Lucas.Mouth's boss Alice gets fired, and Mouth tries to win Millicent back.At the first Raven's basketball game of the season, Haley, Brooke, Peyton, Lindsey and Mia find themselves locked in the Tree Hill High library where secrets abound come forward.With the strike resolved, the CW announced that six more episodes would be produced bringing the episode count to eighteen.Four years after high school; Karen is travelling the world with her daughter, Lily and boyfriend, Andy.The dispute led to a strike by the writers, which has caused a lack in episodes being produced.