In the season four premiere, gang from Beverly Hills have graduated from high school. Naomi has spent the summer dealing with the shocking news of her pregnancy and quickly discovers she doesn’t have the status at college that she did in high school. Annie receives some unexpected news that keeps her in town, while Liam returns from his summer away ready to commit to Annie. Dixon finds himself without a roommate or a place to live, while an unexpected visitor tests Navid and Silver’s relationship after they move in together. Adrianna comes back to town looking for redemption, which she soon learns will be hard to earn back. Ivy and Raj struggle to deal with Raj’s health getting worse, while Teddy struggles with coming out to his family.

Navid surprises Dixon with some studio time to apologize for messing things up with a music producer, where Dixon feels the pressure to create a hit song. Naomi plots revenge to take down rival Holly and her sorority during the Greek games, which requires Austin's help, much to Naomi's dismay. Silver directs a disastrous commercial for Liam's bar, while Ivy feels torn between her relationship and her friends.

Silver is asked to make campaign videos for political candidate Marissa Harris-Young who is running against Teddy’s Uncle Charles for public office. Teddy runs into an old flame and Annie gets stuck with Leila during an important date. A surprise visitor threatens to tear Liam and Jane apart, while Naomi can't shake her growing feelings for Austin during a party to encourage students to vote.

Liam gets offered a modeling job after an agent sees the commercial for his bar, while Annie finds herself starting to fall for an unlikely guy. During a charity talent show event to raise money for an experimental cancer treatment for Raj, Naomi is determined to win the contest in order to show up Austin's out-of-town visitor Sally. While working on his music, Dixon pushes his limits and starts spiraling out of control, which forces Adrianna to confront him.

Navid suspects that Liam and Silver hooked up so he decides to confront Liam on the red carpet of a movie premiere. Annie and Caleb fight their attraction to one another but finally give into temptation. Meanwhile, Naomi has been hired to plan the wedding of an heiress and discovers she knows the groom a little too well, and Austin enlists his dad, Judd Ridge to be help launch Adrianna’s country career.

A reluctant Naomi tries to sabotage the bachelorette party she has to host for Max’s fiancée Madison, where Madison’s childhood crush, Nick Carter, makes a surprise appearance. At Max’s bachelor party, Liam and Navid get into a fight over Silver and the evening comes to an end with people at both parties getting hauled to jail. Meanwhile, Ivy blames Annie and Caleb for Diego having to go on the run.

Naomi shocks everyone when she announces she won’t be able to oversee Max’s wedding because she has accepted a job in New York and will be leaving immediately. Teddy comes back to town and Dixon rushes back from touring to give his relationship with Adrianna another try, then fails to show up at their meeting spot. Meanwhile, Silver feels like she has to choose between Navid and Liam and makes a life-changing decision.

In the season five premiere, Naomi and Max make some big plans that go horribly awry when they both get arrested and land in jail. Liam is forced to put The Offshore up for sale in order to pay off Vanessa and buy out her $200,000 interest in Liam’s movie contract. Navid approaches Liam about becoming his business partner. Teddy is overwhelmed by Silver’s request to father her baby. Adrianna, unaware Dixon has gotten into a life-threatening accident, has an unforgettable evening in Las Vegas with a handsome stranger, Taylor, after she vows to get over Dixon and move on with her life. Annie asks Ade to return to Los Angeles to be with an unconscious Dixon, and the two girls decide to move into the beach house together.

Naomi and Max’s honeymoon plans are put on hold after Alec informs Max that his whirlwind wedding has caused a public relations problem and lowered their tech company’s stock price. Naomi decides to throw a high-class reception to reassure Max’s investors that their marriage isn’t a cause for concern. Adrianna discovers that club promoter Taylor, her one-night stand from Las Vegas, is partnering with Liam and Navid to re-launch The Offshore. Adrianna insists that their fling was a one-time thing, but Taylor suspects she has deeper feelings. At physical therapy, Annie and Dixon encounter fellow patient, Riley, who warns Annie to stop babying Dixon so he can learn how to manage on his own. At home, Dixon explodes on Annie and tells her that he’s tired of her help. Liam offers to buy out Vanessa’s portion of his movie contract, but Vanessa blackmails Liam to be her boyfriend again by threatening to show the police hidden camera footage of Liam. Silver invites Liam to be her date at Naomi’s reception, but gets a surprising answer. Liam confronts Vanessa after the reception, but their argument is cut short by a shocking accident.

Naomi plans a romantic getaway with Max, intending to disclose that Alec kissed her, but when Max persuades Naomi to perform a trust-building exercise, she freaks out when she’s unable to complete it. Silver discovers that nude pictures from her photo shoot have been posted on the internet, and receives help removing them from Annie’s new prospect, Collin. Liam enrolls in Lindsey's business law class, but she assumes he’s not serious about his education. Liam’s new costar, Kendall, is harassing him to begin a relationship with her for publicity, so Liam attempts to escape by going camping with Navid and Dixon. When Liam goes missing in the woods, Kendall seizes the opportunity to alert the media to find him. Meanwhile, Dixon encourages Adrianna to hire Taylor to create her new music video concept. After Taylor dares Adrianna to show him how sexy she can be, she realizes that she has feeling for him.

As Dixon continues to recuperate, Adrianna confides in Annie that she and Dixon are having intimacy issues. Annie grows closer to Colin, but Riley suspects that Colin isn’t who he appears to be. Colin discovers that Alex installed a GPS tracking app on Naomi’s phone so he can track her whereabouts, but Colin reconfigures her phone so she can secretly read Alec’s emails, which exposes Alec’s efforts to sabotage Max’s relationships. 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 secretly seeing each other. Lindsey comes to the opening event to discuss Liam’s business plan, and their animosity gives way to passion.

Liam and Lindsey keep their relationship under wraps, but when Navid's jealous streak gets the best of him, he arranges for Liam and Lindsey's sex tape to be shown in place of Liam's movie premiere at Phenomi-com. Riley admits his feelings to Annie, but Annie's more interested in giving her relationship with Colin a chance.

Meanwhile, Max tries to figure out how his company's video game technology got hacked, so Naomi and Alec work together to demo a new video game at Phenomi-con. Taylor feels guilty for hooking up with Adrianna, so he tells her to end things with Dixon if she wants to be with him. Dixon collapses due to a spinal infection, and Adrianna learns that he stopped taking his pain medication because he was afraid to become addicted again.

When Adrianna opens at the Hollywood Bowl for a headlining artist, Dixon decides to buy her a celebration gift. Suspecting he might propose, Silver convinces Ade to come clean about her affair with Taylor. Annie confronts Riley about standing her up for wrongly suspecting that Annie is uncomfortable with his disability. Naomi encourages Max to hire an executive to replace Alec, but she’s uncomfortable when the perfect candidate-on-paper turns out to be a gorgeous girl, Bryce Albright. Liam receives a threatening letter that suggests the anonymous source knows the truth about Vanessa’s disappearance, and he’s relived when off-duty L.A.P.D. officer, Ashley Howard, becomes his bodyguard.

Naomi hosts an elaborate charity lingerie show at the Playboy Mansion in an attempt to gain membership status with the elite ladies West Beverly alumni group. Silver surprises her West Beverly High friends by performing burlesque at this stylish Homecoming event. Liam confides in Annie about Vanessa’s accident and tells Annie about the blackmail threats he’s received. Liam also accepts Navid’s apology for leaking Liam’s sex tape and offers Navid the chance to manage The Offshore. While Dixon is making big plans for Adrianna’s career on his new record label, he discovers that Ade had other desires aside from music.

When Alex approaches Max about forming a new company with him, Naomi intervenes by attempting to persuade Bryce to rehire Max at his company. Naomi convinces Navid to take Bryce out for drinks, and after a few cocktails Navid uncovers the truth about Max's termination, which leaves Naomi pondering the fate of her marriage. Then, Liam receives a blackmail letter about Vanessa's accident, and Annie agrees to lend him the money to help trap his blackmailer. But when Adrianna tells Ashley that she spotted Vanessa at the beauty salon, Ashley wrongly suspects that Liam was headed for a secret rendez-vous with Vanessa.

Meanwhile, Silver is distraught when Teddy refuses to sign over his parental rights and tries to convince her to let him co-parent the baby.

Annie experiences an alternate reality about what life would have been like if she had stayed in Kansas, including being engaged to her high school boyfriend. In the alternate world, Dixon becomes a massively successful hip hop artist who no longer has contact with his family, while Adrianna is a washed-up actress and Hollywood’s bad girl. Naomi is a real estate agent, and Teddy has not revealed his true sexual orientation.

Naomi and Max see a marriage counselor to decide if they are going to stay married, while Teddy tells Silver he won’t ruin her chance to have a baby if she agrees to his terms. Navid uses Liam’s celebrity status to help him get into an elite secret society and Annie rushes to tell Riley her true feelings before he undergoes an experimental surgery.

Naomi and Max co-host a charity football game which re-kindles old feelings, while Navid pushes Liam to continue underground fighting. Adrianna purposely sabotages a performance so Dixon will let her out of her contract, and Annie’s blog gets the attention of a publisher.