Teddy continues throwing his charm and weight around by inviting some of the gang to a day-long sailing trip on his father's yacht. There, more relationship troubles hit them. Dixon tries to move on from Silver by inviting over Sasha to whom he lies about his age to impress her. Navid begins to doubt about where his relationship with Adrianna is heading. Adrianna begins to show more appreciation to Teddy, while he continues to rebuff Naomi's further attempts at flirtation. Meanwhile, Annie, broken and humiliated from the nude photo of her that was posted to the entire student body, commits herself on a hell-bent mission to expose Naomi as the perpetrator. Both Harry and Debbie begin to worry about Annie's recent behavior and try to arrange a sit-down of talks with her. However this only stirs up more tension as Annie becomes more bellicose, refusing to talk to anyone. Harry then confides in Kelly about Annie's behavior - Kelly suspects that Annie's hiding something. Elsewhere, Liam is frustrated and disgusted at Annie and Naomi's continuing vicious feud. Neither one of them wants to associate with Liam anymore, so he confines himself to his garage where be begins working on a dark "project".

Dixon and Sasha continue their whirlwind romance despite his friends advice that he's moving too fast with it. That weekend, Dixon and Sasha drive up to Napa's Wind Country to sample some wine. But on the return trip, a flat tire leads to the discovery of a car trunk full of pornography, and a series of lies that Dixon makes up. Annie's new confident attitude quickly disappears when she realizes that Jasper, a new student at West Beverly, is nephew of the derelict that she hit on prom night. Navid assigns Silver and Gia to interview Jasper for a news piece about his uncle whom was a student at West Beverly, and who left behind a $100,000 inheritance to the school. Annie tries to befriend Jasper who confides in her about how his uncle lost everything, ending up homeless, and of Jasper's uncertainty with it all. Elsewhere, Navid continues to grow insanely and immaturely jealous over Adrianna's friendship with Teddy, with whom she confides about her uncertainty with Navid and of his envy. Elsewhere, Liam finally finds a way to get revenge on the psychopath Jen to make her reveal the truth to Naomi about her seducing him that night of the prom party when he discovers that Jen scammed a fortune out of a French husband that she married for money. But Jen has other ideas to slither out of the predicament she's in.

Naomi learns that her SAT test scores may not be high enough for her to be accepted into California University. She devises another devious plan to be tutored by Richard, the son of the school's dean of admissions, but she quickly turns her attention to a hot CU student named Jamie. Meanwhile, Dixon continues down his own dark path by continuing to lie to Sasha about his real age. But Sasha already becomes suspicious about Dixon's age. After doing a little underhanded investigating, Sasha learns that he's still a senior in high school, and she breaks up with him. Navid and Adrianna go on a double date with Teddy and his latest girlfriend. But Adrianna's growing feelings towards Teddy make for an awkward situation, and it leads to Navid's renewed jealousy. Elsewhere, Silver accompanies Adrianna to a local Alcoholics Anonymous meeting where they surprisingly run into Silver's mother, Jackie. She tells Silver that she would like to re-establish their relationship. But Silver angrily refuses because of the years of unapologetic abuse. Later, Jackie confides in Adrianna about a shocking health problem she has.

Both Kelly and Silver deal with the shocking news that their mother, Jackie, is dying of breast cancer. Kelly doesn't want to be sucked back into her mother's bad behavior which continues to persist, but Silver feels differently and wants to re-bond with Jackie. Meanwhile, Navid is devastated when Adrianna tells him that she needs time alone, but she turns to Teddy for attention. Jen continues to manipulate Naomi with her charming personality and manages to convince Naomi to lend her a large amount of cash which Jen plans to use to invest in a race horse. Elsewhere, Jasper rescues Annie from a bad date and the two become fast friends. Also, Harry, seeking to get away from problems at home, accompanies Ryan to a bar for some guy time and attempts to be his wing man when Ryan wants to move on from Jen.

Silver and Kelly continue to argue about caring for their dying mother, in which Kelly wants nothing to do with their drunk of a mother, Silver wants to spend her time caring for her. While dealing with schoolwork and caring after school for Jackie, Silver is paired with Teddy for a class project where they find they have more in common when he tells her that his mother too died from cancer. Meanwhile, Naomi continues her relationship with Richard, but continues to flirt with Jamie. Although coming clean with Sasha, Dixon realizes that he and her are in two different places in their life and decides to break up with her, but she later tells him some "life-changing news". Tensions escalate between between Debbie and Harry when she walks in on Harry and Kelly talking in his office, and Debbie's jealousy and suspicion gets the worst of her. Elsewhere, Annie and Jasper's relationship is put to the test when he attempts to convince her to steal a car while shooting a scene for his student film. Also, Liam butts heads with Ivy, the newest member of the surf team. Most of the gang attend a Halloween costume party at the Beverly Hills Beach Club where Adrianna dresses up as Marilyn Monroe to help her deal with the end of her relationship with Navid.

Navid and Blaze News employee, Gia, launch an investigation into student drug use at West Beverly, which leads them to Annie's boyfriend, Jasper, over his history of past drug use which he claims to be over with. While Annie wants to believe Jasper's side of the story, she becomes doubtful when both Navid and Gia tell her that Jasper has always been using. In the meantime, Navid receives dating advice from Samantha Ronson. Liam gives up on trying to win back Naomi, and seeks company with Ivy at the Edison while Teddy sets his sights on her as well. Worried that Adrianna will relapse into drugs, Naomi and Silver enlist Navid's assistance to talk to her, but he is too consumed by his ego and jealousy to care about her anymore. Meanwhile, Dixon reveals his situation with Sasha to Debbie and Harry, prompting Debbie to do some investigating to see if Sasha is telling the truth. Also, Jen and Ryan meet up with Pharrell to watch a performance of N.E.R.D.

Silver plans a cancer-awareness charity event to honor her mother and enlists the help of Navid, Dixon, Liam and Teddy to appear in a bachelor auction. Ian, a theater student at West Bev, is brought in to help choreograph a dance number for the auction, but all comes to a stand-still when Teddy directs some negative words toward him. Annie and Adrianna discover the truth about Naomi and Mr. Cannon. Annie discovers Debbie's financial problems and decides to take an offer to make some quick cash. Ivy and Dixon decide to spend the night together, but Dixon hits the brakes when Sasha returns with some life-altering news.