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.

Silver has yet to schedule her insemination appointment, and worries that she’ll no longer be attractive after undergoing the preventive surgeries. Adrianna encourages Silver to treat herself to an irresponsible day of fun doing all the things that she won’t be able to do once she becomes a mother. Alec ignores Naomi’s gestures to make nice, so Naomi poses as a wealthy investor and lures him to her yacht for a phony business meeting. The two reach an agreement to get along, and Alec spontaneously kisses Naomi, which she rebuffs. Alec apologizes, but Naomi insists on telling Max, unaware that Alec had planted the kiss to blackmail her. Meanwhile, Annie thinks that Riley is too hard on Dixon, but Riley insists that Dixon needs to change his attitude in order to accelerate his recovery. Liam learns that his video game contract can’t be finalized without Vanessa’s approval, so Annie encourages him to speak with her attorney, Lindsey Beckwith. Liam worries when a detective shows up asking questions about Vanessa’s whereabouts.

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 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.