When Taylor learns about Ryan's sleeping problems she devises a plan to help him but must then turn to Kaitlin when her plan backfires. At Brown Summer and Che step up their activism and it lands them more freedom than imagined. Julie also gets help from Kaitlin to help save the dating service.

Kaitlin takes down the school mean girl by throwing a rager at her house. Sandy and Kirsten find time to bond with Ryan while Seth is away visiting Summer at Brown but all he finds is an empty dorm room. Meanwhile Julie continues work on the dating service and finds out a new surprise.

Chrismukkah once again returns to the Cohens. Ryan and Taylor have an accident while putting up the holiday lights and they end up in a sort of parallel universe, where all is not like it is meant to be, since Ryan does not exist. While - in the real world - everybody is worrying about them, except Taylor's mom, they eventually manage to fix things, also thanks to a letter from the past.

Kaitlin is assigned a tutor after she presented a ruffled report to her class. Julie comes clean to Kirsten about who Frank really is. Summer and Seth continue their recent commitment despite how they really feel about it. When Ryan's dad comes to the Cohen's for dinner things don't go as planned.

Taylor's ex-husband comes to Newport and causes a rift in her relationship with Ryan. Seth goes to Seattle to obtain Dr. Roberts blessing, while Summer "travels to the past" for 48 hours. Kaitlin finds love, while Julie finds problems with Kirsten.

Sandy, Ryan and Seth prepare for Kirsten's upcoming 40th birthday party, however Kirsten learns some news that will change her life forever. Kaitlin tries to stop her mother having a secret love affair. Taylor visits a therapist and Ryan pretends that he doesnt miss her. Elsewhere Che finally learns that Seth isn't his soulmate.

Seth and Summer come upon a fortune teller whose prediction makes the two question whether they are truly meant for each other. Ryan gets back in touch with his father (with a little help from Taylor). When the two teens discover a love connection between Frank and Julie despite her pending engagement, a Valentine's competition is sparked between "Team Bullit" and "Team Frank". Meanwhile, with a new baby on the way, Kirsten finds herself dwelling on an old secret involving Jimmy Cooper.