Silver is coerced into spending the entire day with Adrianna, doing risk-taking challenges, a carefree adult in their 20s would do after she keeps putting off her insemination appointment. She later has a naked photo shoot, thanks to a suggestion from Naomi. While Max is away on business, Naomi does everything she can to have Alec like her and later, when they soon begin to bond, he kisses her, putting her in a tough position of whether or not to tell Max. Meanwhile, Annie has a reluctant Dixon meet with a therapy group at CU, when he loses hope at ever walking again and meets Megan, the daughter of the dead truck driver that caused Dixon's car accident. When a police detective begin questioning Liam about Vanessa's whereabouts, he contemplates telling the truth about the accident and facing serious jail time until he learns that the police have discovered Vanessa's criminal history and believe that she has simply run off again, leaving Liam relieved.

As Dixon continues to recuperate while receiving strange back pains, Adrianna confides in Annie that she and Dixon are having intimacy issues. Frustrated with Dixon's dedication to his career at the re-opening of Navid and Liam's new nightclub, the Pop Up, Adrianna goes to re-consummate her relationship with Taylor. Meanwhile, Navid hopes to show Silver how successful he's become with the launch of the Pop Up, but he becomes suspicious that Silver and Liam are seeing each other. Elsewhere, Silver continues her secret profession of burlesque dancing as an outlet for her emotions. Lindsey comes to the opening event to discuss Liam's business plan, and their animosity gives way to passion. Navid confiscates a attendee's phone and discovers a video of Lindsey and Liam having sex. Annie grows closer to Colin, but Riley suspects that Colin isn't who he appears to be. Naomi brings Max's former fiancée, Madison, to try to get her to reveal that Alec tried to destroy her own engagement with Max and in the process show Max the type of person Alec really is, but it doesn't go according to plan.

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, now in a coma and fighting for her life during surgery after being shot, wakes up and finds herself in an alternate reality where she sees what life would be like if she and her family never moved to Beverly Hills. Annie discovers herself working as an actress in a summer stock theater in Kansas and engaged to her old high school boyfriend, Jason. Annie also learns that her parents got divorced anyway, but Dixon is living in California and is a successful rap star, but to her dismay, no longer keeps in touch with his family and is living a reckless life. Navid happens to be Dixon's manager who tries to keep him under control to protect his image. Annie travels to Los Angeles and meets Naomi who works as a real estate agent had she never won her trust fund back. Teddy is a successful tennis pro-player, but has still never told anyone about his real sexual orientation. Adrianna is a successful actress and Hollywood's "bad girl" having never quit drinking, drugs or partying. Silver is a cynical Internet blog writer who isn't close to anyone and has her own website of writing dirt on celebrities. Liam is revealed to be attending college but has problems with delivering drugs for Dixon as to pay off a debt he owns to his old school rival Ty.

Naomi and Max seek the help of a marriage counselor, who advises Naomi to work on herself which leads her to plan a toddler's beauty pageant. After going on countless interviews, Max realizes that what he really wants to do with his life is attend a program at MIT. But Naomi doesn't want to move to Massachusetts. Meanwhile, Megan can't afford to stay at CU for the next semester unless she gets a scholarship. She refuses to accept help, and won't work for Dixon, in spite if his insistence. So Dixon goes behind her back and sets up an anonymous scholarship for her. But that plan backfires when Adrianna discovers that it was her hard earned money for Dixon's label that he used to fund the scholarship. Navid attempts to enroll at CU in order to pledge to be tapped by a secret society. Navid also learns that Teddy's embryos are Silver's one and only chance of having a baby, he goes to Teddy and demands that he let Silver have them. Reluctantly, Teddy agrees. But when Silver visits Teddy's lawyer, she realizes that there's a catch. Silver must find a surrogate mother, meaning she can't give birth to her own baby. Liam gets kicked out of a boxing gym because he sparred too violently as he continues to take out his anger and frustration over his kidnapping. Also, Annie learns that Riley is undergoing experimental back surgery in order to walk again. With Dixon's help, Annie rushes to the hospital in the hopes that she can stop him. When she arrives, the surgery is already complete. He seems perfectly healthy until later that night when Annie calls to check on him and learns that he suffered a blood clot in his lung and passed away.