As the fifth season opens, the series flashes forward four years to postcollege life. While most of the gang struggle to find their footing in the working world, now-famous fashion designer Brooke faces the challenges success brings her in New York City.
Lucas finally gets past his writer's block; Brooke and Peyton move forward with their new business ventures; Mouth continues to clash with his boss, leading him to take some questionable advice from Skills; Nathan visits Dan in prison. Kevin Federline guest stars.
Brooke forges ahead with the opening of her new store; and Nathan makes an effort to help a difficult high-school basketball player. Meanwhile, Peyton must deal with an increasingly arrogant musician; and Haley rediscovers her interest in music.
In this flashback-heavy episode, Lucas reminisces about his first year of college, during which he coached Nathan's basketball team alongside Whitey and struggled to maintain a long-distance relationship with Peyton.
Victoria stirs up trouble at Peyton's new label, and Lindsey finds out how Peyton really feels about her. Meanwhile, Jamie has questions about his Grandpa Dan, and Mouth has doubts about his relationship with his boss.
The gang hangs out at Tric for the night, where Mouth discovers that Brooke has set him up on a blind date with Millicent. Meanwhile, a nervous Mia learns that she's about to make her solo live debut; and Lindsey tries to avoid Peyton.
Brooke continues to try to make progress in her pursuit of Owen the bartender; and Haley is conflicted about what to do regarding something she saw at Tric. Meanwhile, Mouth tries to redeem himself in the eyes of a potential new love interest; and Quentin's recent actions could negatively influence the season-opening game.
When the gals get locked in a library, Peyton and Lindsey have an opportunity to argue about Lucas; Brooke plays defense when others attack her mom; and Haley mentors Mia. Elsewhere, Mouth gets his first on-air assignment; and Lucas and Nathan each wrestle with how truthful to be regarding recent events in their lives.
On the eve of their impending nuptials, Lucas and Lindsey try to help a couple who are facing problems. Meanwhile, three old faces return to town, among them Rachel; and Brooke has to deal with Victoria.
Lucas and Lindsey's wedding day arrives, and Peyton must decide how she should handle this momentous occasion. Meanwhile, Nathan reaches out to Haley; and a mini family reunion takes place at the wedding.
Lucas and Peyton finally talk about his unsuccessful nuptials, while Mouth and Millicent take a new step forward. Meanwhile, Haley and Nathan both make decisions about their careers; and Brooke gets an important phone call.
Jamie celebrates his fifth birthday, and Lindsey returns to town to attend his party, giving Lucas hope for a reconciliation. Meanwhile, Brooke makes preparations in her life for a new baby; and Dan, hoping to reconnect with his family, shares a dark secret with Nathan.
Lucas investigates the supposed progression of Dan's heart condition as Haley deals with letting Dan develop a relationship with Jamie. Meanwhile, Mouth gets a chance to be a sports anchor; and Nathan gives Quentin advice about getting his game back.
Lucas is hurt by devastating news, and he makes a surprising revelation to Peyton. Elsewhere, Brooke's foster baby has an emergency operation; and Skills and Nathan take a risk as they try to turn the Ravens' season around.
In the fifth-season finale, Brooke must give up her foster baby and Lucas has to deal with what happened on game night. Meanwhile, Haley's music career takes a positive turn and Peyton hears news about someone from her past.