After having spent most of their vacation time in summer school due to Annie’s report of Naomi’s party to the police, the gang decides to enjoy the last few days of the summer at the Beverly Hills Beach Club, where they meet new student Teddy. As destiny would have it, their time together in school during the summer has led to the formation of a close friendship between Silver, Naomi, and Adrianna. Annie, however, has resorted to remaining aloof from her friends and family due to her guilt over the hit-and-run fiasco. Meanwhile, Navid makes plans to take his relationship with Adrianna to new levels and lose his virginity, all while Dixon receives a text message that causes him to consider ending his relationship with Silver.

The rumor about the existence of a naked photo of Annie runs wild throughout the West Beverly Hills High community, causing further divide between Dixon and his sister. Despite his problems at home, Liam joins Teddy and Dixon in trying out for the surfing team. Meanwhile, Ryan worries about his relationship with Jen, and Naomi continues scheming new ways to make Annie’s life miserable.

Annie, humiliated by the mass sext message, sets out to prove that Naomi sent the message. Harry and Debbie try to talk about Annie’s situation, but their discussion only causes more tension, leading Harry to confide in Kelly about his family issues. Dixon meets the girl of his dreams, Sasha, but hides his true age in order to get to know her. Meanwhile, Silver continues to try to get over Dixon; Adrianna and Navid deal with Teddy; and Liam begins working on a mysterious project.

Dixon and Sasha continue their whirlwind romance by driving to Napa for the weekend, but on the return trip a flat tire leads to a trunk of porn and a bunch of lies. Annie’s confident attitude quickly disappears when she realizes that Jasper, the nephew of the man she hit on prom night, is a student at West Beverly. Navid continues to run the Blaze News and assigns Silver and Gia to interview Jasper for a news piece about his uncle. Things get steamy when Adrianna confides in Teddy , resulting in Adrianna and Navid finally spending the night together. Liam finally finds a way to get revenge on Jen and reveal the truth to Naomi about their night together at prom.

Naomi learns that her test scores may not be high enough for her to be accepted into CU. Devastated, Naomi devises a plan to be tutored by Richard, the son of the school’s dean of admissions, but quickly realizes she would much rather be studying Jamie, a CU student. Dixon’s girlfriend, Sasha, becomes suspicious about his age and does a little detective work to learn the truth, leaving Dixon devastated. Navid and Adrianna double date with Teddy, but Adrianna’s growing feelings towards Teddy make for an awkward situation. Silver accompanies Adrianna to an AA meeting and surprisingly bumps into her mom, Jackie, who tells Silver she would like to re-establish their relationship. An angry Silver rejects her mother, but her world is turned upside down when Adrianna reveals shocking news about Jackie.

It’s Halloween at the Beverly Hills Beach Club and Adrianna (Jessica Lowndes) channels Marilyn Monroe to help her deal with the end of her relationship with Navid (Michael Steger). Silver (Jessica Stroup) and Kelly (Jennie Garth) continue to have differing opinions about caring for Jackie (Ann Gillespie). Silver is overloaded with school work and caring for her mom, but soon learns that she and Teddy (Teddy Donovan) have more in common than a class project. Naomi (AnnaLynne McCord) continues her relationship with Richard (guest star Jonathon Trent, “CSI: NY”), but when she and Jamie (guest star Travis Van Winkle, “Meet the Spartans”) share an intimate conversation, her plans to schmooze with the dean of CU come to a screeching halt.

Silver and Kelly deal with shocking news about their mother; Adrianna turns Navid’s world upside down; Jen asks Naomi to loan her a large sum of money; Jasper saves Annie from a bad date.