Dixon and Sasha continue their whirlwind romance by driving to Napa for the weekend, but on the return trip a flat tire leads to a trunk of porn and a bunch of lies. Annie's confident attitude quickly disappears when she realizes that Jasper, the nephew of the man she hit on prom night, is a student at West Beverly. Navid continues to run the Blaze News and assigns Silver and Gia to interview Jasper for a news piece about his uncle. Things get steamy when Adrianna confides in Teddy, resulting in Adrianna and Navid finally spending the night together. Liam finally finds a way to get revenge on Jen and reveal the truth to Naomi about their night together at prom.

Naomi learns that her test scores may not be high enough for her to be accepted into CU. Devastated, Naomi devises a plan to be tutored by Richard, the son of the school's dean of admissions, but quickly realizes she would much rather be studying Jamie, a CU student. Dixon's girlfriend, Sasha, becomes suspicious about his age and does a little detective work to learn the truth, leaving Dixon devastated. Navid and Adrianna double date with Teddy, but Adrianna’s growing feelings towards Teddy make for an awkward situation. Silver accompanies Adrianna to an AA meeting and surprisingly bumps into her mom, Jackie, who tells Silver she would like to re-establish their relationship. An angry Silver rejects her mother, but her world is turned upside down when Adrianna reveals shocking news about Jackie.

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, but Silver feels differently. Navid's world is turned upside down when Adrianna reveals that she needs time alone, but turns to Teddy for attention. Jen continues to manipulate Naomi and manages to convince Naomi to lend her a large amount of cash. Jasper rescues Annie from a bad date and the two forge a bond that will be hard to break. Harry accompanies Ryan to a bar for some guy time and attempts to be his wing man.

It's Halloween at the Beverly Hills Beach Club and Adrianna channels Marilyn Monroe to help her deal with the end of her relationship with Navid. Silver and Kelly continue to have differing opinions about caring for Jackie. Silver is overloaded with school work and caring for her mom, but soon learns that she and Teddy have more in common than a class project. Naomi continues her relationship with Richard, but when she and Jamie share an intimate conversation, her plans to schmooze with the dean of CU come to a screeching halt. Dixon realizes he and Sasha are in two different places in their life and decides to end their relationship, but she ends up delivering life-changing news. Tensions rise between Debbie and Harry when she walks in on Harry and Kelly in his office. 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. Liam butts heads with the newest member of the surf team, Ivy.

Navid and Gia launch an investigation into student drug use at West Beverly for Blaze News, which leads them to Annie's boyfriend, Jasper leaving Annie torn over who to believe. Fresh off his break-up with Adrianna, Navid receives dating advice from Samantha Ronson while out with Liam, Teddy and Ivy at the Edison. Worried that Adrianna will relapse, Naomi and Silver enlist Navid's assistance. Dixon reveals his situation with Sasha to Debbie and Harry, prompting Debbie to do some investigating. Jen and Ryan meet up with Pharrell to watch a performance of N.E.R.D.

With the help of Teddy, Jackie surprises Silver with a half-birthday celebration that takes her back to her childhood birthday parties. Navid witnesses Adrianna buying drugs from Jasper, forcing Navid to confront him about being a drug dealer. Dixon is determined to confront Sasha about her miscarriage, forcing Debbie and Harry to reveal that Sasha lied about being pregnant. Annie and Jasper profess their love for each other and decide to take their relationship to the next level. After getting into a fight on the beach, Liam, with the help of Dixon, Teddy and Ivy, devises a plan seek revenge on Jen.

Annie leaves Debbie and Harry surprised when she informs them that she would like to invite Jasper over for dinner. Dixon decides to pass on the event as a result of his anger over Debbie's management of the Sasha situation. Meanwhile, Kelly shows support for Silver regarding the caring of Jackie despite the fact that she does not yet know if she can ultimately forgive her mother for all the pain she has caused in the past. Navid confronts Adrianna about her drug use, and a weekend camping trip leads to Ryan and Jen's relationship climbing to a new level. Also, Naomi is caught kissing Jamie by Richard and his mother, forcing her to come clean about her plans for CU admission.

Navid wakes up in the hospital but has no memory of who pushed him down the stairs. Adrianna visits Navid and following her conversation with him, makes a life-changing decision about her addiction to pills. Silver and Teddy bond over the loss of both of their mothers and unexpectedly get close. Liam, Dixon and Ivy learn that Naomi and Jen will be attending the horse races and devise a plan to finally reveal the truth to Naomi about her evil sister. Annie and Jasper sneak out even though Harry and Debbie have grounded her.

Navid is convinced Jasper pushed him down the stairs and turns to Adrianna to help reveal the information. Annie is confronted by her friends about Jasper's drug dealing but when she confronts him about the news he reveals his suspicions about her involvement in the hit and run. Naomi and Silver decide to spend Christmas break in St. Barts but first make an appearance at the beach club for the winter dance. Teddy reveals his feelings for Silver, causing Dixon to be jealous, while Naomi and Liam attempt to forgive each other for what happened with Jen. Debbie attempts to spend some quality time with Dixon by taking him to the arcade.

Naomi returns from her vacation in St. Bart’s excited to spend time with Liam, which leads to the two getting up close and personal in his newly built boat. Adrianna and Gia bond during an AA meeting and establish a support system for each other which leads to the two sharing a kiss at the Beach Club. Navid and Dixon devise a plan to eliminate Jasper from Annie’s life, but never anticipate the outcome of a school drug search. Dixon attempts to rekindle his relationship with Silver, while Silver hides her true feelings for Teddy. Harry and Debbie run into Kelly while attending a school function and Debbie confronts Kelly about having a crush on Harry.

Naomi enlists Ivy’s help in reducing the awkwardness with Liam and the three decide to go on a hike, something Naomi has never done. Naomi discovers Ivy’s alterior motives and confronts her by pushing her face in the sand. Naomi, Silver and Adrianna go shopping in the Palisades and run into Annie and Jasper. Jasper blackmails Annie with photographic proof of her hit-and-run, but she gives Jasper an ultimatum that puts her mind at ease. Adrianna and Gia’s friendship continues to develop when the two throw a pity party for themselves. Silver and Teddy toy with the idea of trying to make a relationship work. Ryan meets free-spirited Laurel at a bar, but soon they move to her car so they can get to know each other even better. A surprise visitor shows up on the Wilson’s doorstep.

Gia encourages Adrianna to audition for a new band and admits she has a crush on Adrianna. Dixon's birthmother, Dana drops by for a surprise visit and tries to develop a relationship with her son. Silver and Teddy go on their first official date but Silver finds it difficult to deal with Teddy's playboy past and enlists Naomi's help to track his whereabouts. Navid returns from his suspension to find that Naomi has started a gossip segment during Blaze News, which he adamantly opposes. Navid decides to get back into he dating scene by asking Lila out on a date, his first since breaking up with Adrianna. Annie realizes that Jasper has started following her around town. Debbie confides in Kai, her yoga instructor, about the arrival of Dixon's birthmother.

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.