Naomi is asked by her new party planner boss Rachel to oversee her arch-nemesis Holly’s birthday party, while Annie breaks into Jeremy’s apartment in a desperate attempt to get the proof she needs to keep her inheritance. Navid finds trouble after going with his Uncle Amal to make a deal with a potential buyer, and Liam discovers shocking news about Annie.

Naomi embarrasses herself in front of her boss Rachel in an attempt to get over her break-up with Austin. Dixon and Adrianna are booked to perform at a club, where they realize that working together might be a bad idea. Meanwhile, Silver takes her relationship with Greg to the next level and a party Annie throws ends up being a disaster because she is too distracted by Liam's new relationship.

Naomi is determined to fix the relationship between her boss Rachel and her daughter Holly, which forces Holly and Naomi to work together. Greg asks Silver to move to New York with him and Navid finds out some shocking information about Greg’s daughter. Annie discovers Liam’s girlfriend Vanessa might have been involved with his motorcycle accident.

Annie has to make a decision that could expose her work as an escort when Dixon gets arrested in connection with a fire at a sorority house. Adrianna and Silver attempt to put their past behind them, which results in disaster for Silver's relationship with Greg. Vanessa helps throw a party to re-launch Liam's bar, where the All-American Rejects perform.

In an effort to put her inheritance to good use, Annie volunteers to organize a big charity fundraiser. When Naomi takes drastic measures to land her first event-planning client, her big plan back-fires. Meanwhile, Silver realizes she still has feelings for Navid, and Vanessa vows to make Liam a huge star after his agent drops him.

Naomi’s sister Jen arrives with her son for a surprise visit. Adrianna and Dixon land a meeting with a major movie producer to discuss music on his next film, but are sabotaged by Vanessa. Meanwhile, Silver gets accepted into New York University and Ivy attracts attention in the underground scene when she switches to a less conventional style of art..

Naomi is convinced that Annie’s new business partner P.J. is the perfect man for her, but discovers her sister Jen is also interested in him.. Adrianna and Dixon land a spot in a music festival, where Train performs and a record executive offers Dixon a recording contract. Adrianna tells Liam her suspicions that Vanessa staged the near drowning incident.

Dixon collapses while arguing in the recording studio with Adrianna. In the hospital, they run into Liam who is with Silver to support her during a test to detect if she has the breast cancer gene. Ivy finds out Raj still has cancer and is in the hospital, while Annie meets a new guy Caleb and discovers he is a priest.

PJ proposes to Naomi and Annie discovers he needs to get married in order to get the rest of his trust fund. Dixon confesses to Navid that he signed a record contract but admits he did not tell Adrianna because the label didn’t want to sign her. Dixon also accepts a gig to play back up for Haley Reinhart, but doesn’t tell Adrianna. Liam asks Vanessa to move out and discovers she has emptied their joint bank account.

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 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 and Vanessa search for Liam after discovering that Ashley was falsely posing as his studio-hired bodyguard. Needing a break, Naomi goes on a road trip with Adrianna, only to have her wedding ring stolen. Meanwhile, Dixon fails to convince Megan he is over Adrianna.