Annie and Riley's relationship suffers when Riley gets upset at the fact that Annie doesn't treat him like her other boyfriends just because he is in a wheelchair. Meanwhile, Adrianna finds out that she is performing at the Hollywood Bowl and thinks Dixon is going to propose to her after reading a text message on his phone. She then contemplates revealing that she cheated on him, but she doesn't when Dixon gives her a pair of beautiful diamond earrings and wants her to sign to his future record label. Naomi grows jealous when the replacement for Max's business partner is a hot young woman named Bryce and decides that she should be his partner instead. Silver is upset at the fact she still isn't pregnant and discovers that she may need surgery. Liam goes crazy after punching a paparazzi and getting arrested. His studio sends him a bodyguard, a female cop named Ashley Howard, but she later turns out to be an obsessed psychopath when she gets a picture of Liam tattooed on her back.

Naomi wants to get into a West Beverly High Alumni group, who are throwing an alumni event at the high school and does everything in her power to get in, such as donating a building, injuring her opponent in a football game, and throwing an after-party at the Playboy Mansion. Naomi also learns that Bryce double-crossed Max and had him fired so she could take over his job. Teddy returns for the alumni event and tells Silver that Shane broke up with him. Teddy and Shane decide to continue their relationship but Shane gets mad when he finds out Teddy and Silver are having a baby and tells him that they need to talk. Meanwhile, Dixon is happy when Adrianna signs with his record label until he finds the video of Adrianna kissing Taylor and she is forced to come clean about her tryst with Taylor. Adrianna's worst fears are realized when Dixon takes the news very badly and breaks up with her. But before she leaves, Dixon tells her that even though they are no longer together, he still owns her due to her signing with his record label also plans on giving her a very hard time. Annie gets a double blast from the past when she sees her ruthless overachieving cousin, Emily Bradford, at the event and finds out she is now a successful blogger, making her feel like she is a failure. She also sees her former flame Jasper Herman, who wants to apologize to Liam for what happened between the three of them, two years ago. When Liam continues to get threats about Vanessa, he tells Annie about what happened to Vanessa and the two confront Jasper, who reveals he is now in film school and wants Liam to read his script as a sign of forgiveness, plus Jasper knows nothing about Vanessa. Liam accepts Jasper's offer. Annie decides to start her own blog and writes about her relationship with Patrick.

With Max unemployed, Alec returns and offers to help him form a new computer company. Naomi attempts to persuade Bryce to rehire Max at his company after she takes over ownership, but she refuses. Naomi convinces Navid to take Bryce out for drinks to find out why she betrayed and ousted Max from his company. After a few drinks, Navid learns from the half-drunk Bryce that Alec set up Max's firing. Meanwhile, Annie decides to sign up for a writing program in Scotland for the next two years and gets Riley a tablet as a Christmas present, as a way of telling him which in turn angers him into thinking Annie doesn't want him to go with her because he is in a wheelchair. Elsewhere, Silver is distraught when Teddy refuses to sign over his parental rights and tries to convince her to let him co-parent the baby. Adrianna wants to reconcile with Dixon after he has been torturing her with work. Dixon tells Megan that he was in the accident that caused her father's death and instead of getting mad, she forgives him. Elsewhere, Liam receives another blackmail letter about Vanessa's accident which the blackmailer demands $500,000. Unsure who to trust, Liam shows the letter to Annie who agrees to lend Liam the money to help trap his blackmailer. But when Adrianna tells Ashley that she spotted Vanessa at a beauty salon, Ashley wrongly suspects that Liam is headed for a secret rendezvous with Vanessa and kidnaps him.

Naomi and Adrianna take a road trip along the California coast to get away from their respective life problems, but more complications set in when their money and clothes get stolen from Naomi's car, including her wedding ring which prompts them to venture to a seedy biker bar to find their culprits, where Adrianna hooks up with a young motorcyclist and Naomi ventures to visit her estranged mother. Meanwhile, Liam finds himself held captive by the deranged Ashley in the basement of Offshore who has plans to take him to Mexico, while Annie and Vanessa learn that Ashley is not who she says she is. Dixon prepares a party at Naomi's house to celebrate the opening of his new recording label. Megan tells Dixon that she feels that he is not over Adrianna, so in order to move on, Dixon decides to let go of his anger and not feel anything for Adrianna. Elsewhere, Silver is still having problems with Teddy about the impregnation when he continues to want to be a part of her baby's life, while she wants to raise her child alone. Silver goes to Teddy's uncle to persuade him to drop his attempts to block her procedure, but when Teddy still will not back down, a row occurs which makes things worse for everyone.

Annie becomes somewhat angry at Naomi whom has tracked down their real biological half-brother Mark Holland, a local chef who owns a gourmet food truck and Naomi tries to institute herself into Mark's life by holding a CU Food Truck Cook-Off competition where Wolfgang Puck is judging. Meanwhile, Liam experiences some symptoms of post-traumatic stress disorder while preparing to testify against Ashley, but he continues to refuse to talk about his feelings or deal with them. Navid falls further into the Cronos society's nefarious doings when he learns that Campbell runs a "cheaters club" in exchanging test answers to finals. Also, Silver becomes more overbearing with her surrogate Michaela whom begins to resent being Silver's pampering. Backlisted by the music industry, Adrianna is asked to substitute as a lead singer for a band in a Battle of the Bands competition at CU which Annie throws for Dixon who is looking for new fresh talent.