After Lindsay moves to Chicago with her mom, Ryan is heartbroken and Caleb's confused. Seth, Summer, and Marissa invite Ryan to the mall to get his mind off things. Caleb tags along to vent when Sandy tries to make amends with Kirsten by searching for her wedding ring or even a grand gesture that will take her back to when Sandy first proposed. Meanwhile, Alex learns that Marissa might not be as into her as she thought she would be. Kirsten and Julie call an editor for Newport Living but at the same time Julie's Riverside past catches up to her.

Spring has flung in Newport where Marissa recruits Ryan to help her with Harbor School's Pep Rally Bonfire. Alex accepts that her and Marissa are from two different lives and knows she is fighting a lost cause. Seth is stuck and misses last year's good times while Summer disagrees and tells him it's time to move on. Meanwhile, Julie still doesn't know what she is gonna do about her blackmailer and seeks some advice from Sandy. Kirsten wants Carter to stick with the magazine despite his reservations.

When Ryan's brother, Trey, gets out of jail and gives Ryan a call, the Cohens give him a warm welcome. Though, Ryan knows nothing good can come from it. Zach returns from his Italy trip and gives some news leaving Summer curious and Seth ... not really sure what to think. Meanwhile, after Julie admits her naked mistake to Kirsten, they both agree to get Caleb in on it for more help. Newport Living is officially launched.

It's Trey's 21st birthday and Marissa, anxious to help Trey and Ryan forge a relationship, throws a birthday party for Trey at the Cooper-Nichol mansion that turns out to be a rager. Seth is left in hot water by both Summer and Zach, but why? Sandy wants to continue his friendship with Carter, leaving a confused Kirsten. Meanwhile, Julie shares some memories with an "old" friend and in the process learns a few things and gains a few ideas.

Sandy and the boys devise a plan to save Trey from going to jail after he took the fall for supplying drugs at his birthday party. Kirsten and Carter, fulfilling more than their editorial duties, take a trip to Featherbrook's winery. Meanwhile, Caleb returns home and questions his marriage with Julie.