The students of West Beverly Hills High return to school after a long summer. For some, the new school year seems promising and exciting. For others, particularly Annie, things do not look even remotely as positive. And just as it is revealed that Ethan has left the school, new student Teddy comes into the mix to stir the pot.

The rumor about the existence of a naked photo of Annie runs wild throughout the West Beverly Hills High community, causing further divide between Dixon and his sister. Despite his problems at home, Liam joins Teddy and Dixon in trying out for the surfing team. Meanwhile, Ryan worries about his relationship with Jen, and Naomi continues scheming new ways to make Annie's life miserable.

Annie, humiliated by the mass sext message, sets out to prove that Naomi sent the message. Harry and Debbie try to talk about Annie's situation, but their discussion only causes more tension, leading Harry to confide in Kelly about his family issues. Dixon meets the girl of his dreams, Sasha, but hides his true age in order to get to know her. Meanwhile, Silver continues to try to get over Dixon; Adrianna and Navid deal with Teddy; and Liam begins working on a mysterious project.

Dixon and Sasha head to Napa for the weekend, but a flat tire on the way home leads to a trunk of porn as well as growing lies. Annie's attitude makes a complete change when she learns that Jasper, the nephew of the man she hit on prom night, attends West Beverly. Navid continues running the Blaze News, and has Silver and Gia interview Jasper for an article about his uncle. Meanwhile, Adrianna confides in Teddy, leading Adrianna and Navid to spend the night together; Liam gets revenge on Jen; and the truth is revealed to Naomi about prom night.

Silver has an unpleasant run-in with her mother (Ann Gillespie) at Adrianna's AA meeting; Naomi starts working with a tutor at CU, but soon becomes distracted by a cute student (Travis Van Winkle); and Sasha figures out Dixon's age. Elsewhere, Adrianna and Navid go on an awkward double date with Teddy.

Kelly and Silver deal with news that their mother, Jackie, is suffering from breast cancer. Navid's world is shaken up when Adrianna tells him she needs time alone, but ends up turning to Teddy. Jen continues to use Naomi and convinces her to lend her money. Jasper rescues Annie from a bad date, leading the two to form a bond.

It's Halloween and Adrianna channels Marilyn Monroe to help deal with her broken relationship with Navid. Silver and Kelly take different stances as to how to care for their mother. Naomi continues in her relationship with Richard, but later shares an intimate moment with Jamie. Dixon begins to realize that Sasha is in a different place in life than he is and decides to end their relationship. Tensions arise between Debbie and Harry; Annie and Jasper's relationship is tested; and Liam faces off with the newest member of the surf team.

Navid and Gia (guest star Rumer Willis) 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 (appearing as herself) while out with Liam, Teddy and Ivy (guest star Gillian Zinser) 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 (appearing as himself) 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 after the incident, but has no memory of who pushed him down the stairs. Adrianna visits Navid at the hospital which leads her to make a life-changing decision about her drug addiction. Silver and Teddy begin to bond of their shared experiences of their mothers dying. Liam, Dixon and Ivy discover Naomi and Jen will be at the horse race, and decide to put together a plan to tell Naomi the truth about her sister. Meanwhile, Annie, despite being grounded, sneaks out to be with Jasper.

Navid, thinking Jasper pushed him down the stairs, asks Adrianna to help him reveal Jasper for what he is. Annie is confronted by her friends about Jasper and his drug dealing, but when she talks to him about it, he tells her he knows about her involvement in the hit-and-run. Naomi and Silver head to St. Barts for Christmas with a stop at the winter dance first. Teddy reveals his feelings for Silver, which makes Dixon jealous.

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 ulterior 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 tells a lie about Mr. Cannon. Adrianna decides to give Gia a chance and Dana spots Debbie kissing her yoga instructor.

Annie tries to cope with Jasper's decision of jumping off the Hollywood sign. Adrianna wants to make her relationship with Gia public. Naomi finds herself in a web of lies. Silver & Teddy compete to see who know the other one better. Ivy & Dixon pretend to go out.

Naomi's lie about Mr. Cannon spreads across the school. When she testifies in front of the school board, Naomi reveals some unexpected information. Annie finally moves on from her relationship with Jasper but feels haunted when she and Sliver drive by the scene of her hit-and-run.

As a result of falsely accusing her faculty adviser of sexual harassment, Naomi is now required to complete community service and publicly apologizes to her peers for the trouble she has caused. The gang is preparing for the SAT's when Silver disagrees with Teddy's decision to skip college to focus on his tennis career and things grow even more tense when she meets his movie star father, Spence. Liam and his father, Finn, reconnect and attempt to rebuild their relationship.

Naomi and Jen are back to wreaking havoc in each others lives. Just when Naomi thinks she has the upperhand, Jen slaps her back into reality. Teddy invites a nervous Silver to meet his father, Spence, for the second time and the meeting doesn't go quite as planned.

Adrianna's new romance with pop star Javier continues to blossom, while Navid continues to work up enough courage to tell her how he feels. Jen has taken control of Naomi's finances and puts her on a tight budget, resulting in an instant meltdown by Naomi.

Teddy seeks revenge after learning that Spence tried to bribe Silver; Liam and Annie share their darkest secrets; Ryan receives a mysterious package.