During the summer, most of the students at West Beverly were forced to attend summer school after Annie anonymously called the police to report Naomi's post-prom party. During the last weekend of Labor Day, Naomi, Silver and Adrianna hang out at the Beverly Hills Beach club. There, Adrianna runs into an old boyfriend named Teddy Montgomery, a tennis player and new student, while Naomi finds him irresistible. Navid also plans on spending his first romantic night with Adrianna, but jealousy gets in the way. Meanwhile, Annie has spent the summer isolating herself out of guilt for the hit-and-run accident that she committed, fearing that someone will discover her terrible secret.

The twisted Naomi continues her personal quest to destroy Annie's personal and professional life by spreading a false rumor about the existence of a nude photo of Annie, which causes a further divide between Annie and Dixon, as well as Annie's parents who continue to worry about her continuing slide down a dark path. Meanwhile, Liam decides to defy his stern and semi-abusive stepfather and try out with Dixon and Teddy for a spot on the school's surfing team. Elsewhere, Ryan worries about his romance with the manipulative Jen who begins to show off her true colors to him.

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.

Jackie asks Teddy to help her plan a surprise half-birthday party for Silver, which makes Silver think back her past childhood birthday parties which were apparently her best times. Meanwhile, Navid witnesses Adrianna buying drugs from Jasper, forcing Navid to confront him about being a drug dealer. But Jasper threatens to reveal some dirt that he has on Navid should he turn him in. Dixon is determined to confront Sasha about her "miscarriage", which forces Debbie and Harry to reveal that Sasha lied about being pregnant. Elsewhere, 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 during surfing practice, Liam confides in Dixon, Teddy, and Ivy about Naomi's sister Jen seducing him during prom night and he wants to devise a plan to seek revenge on Jen.

Kelly continues to support Silver as she deals with Jackie's declining health, despite that she is conflicted about whether or not she can forgiver her mother for the life-long pain and abuse she caused to both her and Silver. Navid confronts Adrianna about her renewed drug use, but this time, she rudely tells him off for turning his back on her. Meanwhile, Harry and Debbie are surprised when Annie informs them she would like to invite Jasper over for dinner at their house. Despite Annie telling Jasper to be on his best behavior, the dinner proceeds very uncomfortably for everyone. Dixon, still alienated and upset with his entire foster family, especially Debbie over her handling of the Sasha situation, declines to join them, and instead teams up that night with Ivy and Navid to set a plan for Liam to tell Naomi the truth about Jen despite knowing that Naomi will not believe them, even with evidence. Elsewhere, Ryan and Jen's relationship is taken to a new level when he convinces her to go on a weekend camping trip. Also, Naomi and Jamie's secret romance is finally found out when Richard and his mother walk in on them in Richard and Jamie's dorm room which finally forces Naomi to come clean about her plans to get accepted into CU.

Liam, Dixon, and Ivy learn that Naomi and Jen will be attending a horse race to watch the racehorse that Jen bought with Naomi's money, and the three of them devise a crafty and very complex plan to finally reveal the truth to Naomi about her evil sister. Ryan also tags along with Jen to the races, and inadvertently learns how Jen acquired the racehorse used to win the race. Meanwhile, Annie and Jasper sneak out to go on a Saturday date even though Harry and Debbie have grounded her for her growing misanthropic attitude. Navid wakes up in the hospital after his "accident" with no memory of who pushed him down a flight of stairs. Adrianna visits Navid and following her conversation with him, makes a life-changing decision about her addiction to pills. Elsewhere, Silver and Teddy bond over the loss of both of their mothers and unexpectedly get close to each other.

The annual winter dance at the Beverly Hills Beach Club is approaching. Navid thinks Jasper was the one who pushed him down the stairs and asks Adrianna to help him prove it. Meanwhile, Annie questions Jasper about his drug dealing, but Jasper avoids the question when he tells Annie about his suspicions of her involvement with his uncle's death. Debbie tries to smooth over her relationship with Dixon with a trip to an arcade. Teddy has feelings for Silver, making Dixon jealous. Liam tries to rebuild his relationship with Naomi now that she knows the truth about him and Jen. Also, Naomi and Silver decide to spend winter break in St. Barts.

Naomi returns from her vacation in St. Bart's excited to spend time with Liam. However, their first date is uneventful since they have nothing in common which leads Naomi seducing Liam aboard his his newly built boat. Adrianna and Gia bond after they meet during an AA meeting and establish a support system for each other which leads to the two sharing a kiss at the Beach Club. Meawnhile, Jasper begins to blackmail Annie by threatening to tell the authorities about her hit-and-run accident if she breaks up with him. Navid and Dixon devise a plan to remove Jasper from Annie's life by planting cocaine in his locker, but they 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. Also, Harry and Debbie run into Kelly while attending a school function and the jealous Debbie confronts Kelly about her having a crush on Harry.

Naomi, Silver and Adrianna go shopping in the Palisades Mall and run into Annie on a date with Jasper. Annie further arouses the girls suspicions when she refuses to give them an explanation why she's still with Jasper despite knowing his true nature. Unknown to everyone, Jasper continues to blackmail Annie with photographic proof of her hit-and-run. But Annie eventually turns the tables on him when she gives Jasper an ultimatum by threatening to drag him down with her in which he backs down and Annie's mind is finally put at ease... so it seems. Afterwards, Naomi tries to be Ivy's friend and they try to end the awkwardness between them by going on a nature hike. But Naomi discovers Ivy's ulterior motive to embarrass Naomi which leads to them getting into a fistfight at the beach. Meanwhile, Adrianna and Gia's close friendship continues to develop when the two of them throw a pity party for themselves while Gia's former girlfriend, tries to win her back. After Dixon comes clean to both Silver and Teddy about trying to keep them apart, they both toy with the idea of trying to make a relationship work. Also, Ryan meets a free-spirited woman, named Laurel, at a bar, which soon leads to them going into Laurel's car for some quick intimacy. But it turns out to be that Laurel is Ivy's hippie mother. Elsewhere, a surprise visitor, whom is Dixon's biological mother, shows up on Harry and Debbie's doorstep.

Gia encourages Adrianna to audition for a lead singing spot in a new all-girl rock band and admits she has a crush on Adrianna who doesn't know how to respond to Gia's revelation. Dixon's birth mother, Dana, shows up at the Wilsons for a surprise visit and tries to develop a relationship with her son. Meanwhile, Silver and Teddy go on their first official date, but Silver finds it difficult to deal with Teddy's playboy swinging past and she enlists Naomi's help to track his whereabouts afterwords. Navid returns to school from his suspension (after being framed by Jasper for the drug possession charge) to find that Naomi has fully taken over Blaze News and even started a gossip segment, which he adamantly opposes. Navid decides to get back into the dating scene by asking the new Blaze volunteer, Lila, out on a date. As Annie reestablishes relations with Naomi, Silver, and the rest of her former friends, she also realizes that Jasper has started following her around town, and is frustrated that she cannot confide in anyone about what is going on with her out of fear that someone will figure out her secret. Also, a worried Debbie confides in Kai, her yoga instructor, about the arrival of Dixon's birth mother.

Naomi clashes with the Blaze's new faculty advisor, Mr. Cannon, over her racy gossip news segment and she is reprimanded in front of her peers which is a major humiliation for her. After failing to convince Navid to back her opinion, Naomi decides to tell a white lie about Mr. Cannon sexually harassing her which soon spins out of control. Meanwhile, Adrianna is now the lead singer of the all-girl band, the Glorious Steinems while she deals with the band's bass player, Lila, who happens to be Navid's latest girl pal. Shortly after, Adrianna confides in Silver and Naomi about her romantic feelings for Gia, as the two go out on their first official date. Elsewhere, Teddy decides to test Silver's commitment to him by attempting to make her jealous by flirting with random girls. Dixon and his birth mother, Dana, continue to bond while he begins to fall into bad habits by doing on-line gambling which she encourages. Liam catches his stepfather with another woman and confronts him with a fist-to-the-face which leads to Liam leaving home. Also, Debbie and her yoga instructor, Kai, share tea and conversation, but Kai oversteps his boundaries when he makes a pass at her. Elsewhere, Annie confronts Jasper about him stalking her and trying to win her back. But later, Annie receives a phone call from Jasper who tells her that he intends to kill himself unless she returns to him.

Annie deals with the outcome when Jasper attempts suicide by jumping from the Hollywood sign, and she becomes more worried that he will tell someone her secret. Meanwhile, Silver and Teddy decide to go on a double date with Liam and Naomi, which makes Dixon and Ivy feel left out, so the two decide to go on a fake date. Adrianna continues her newfound lesbian romance with Gia who becomes frustrated that Adrianna wants to keep it private. When Adrianna and her band performs for the first time at the Beach Club, she confidently decides to reveal her relationship with Gia in a very public way. Elsewhere, Liam encourages Naomi to come forward with her sexual harassment case against Mr. Cannon, which causes her to continue her lie.

A guilt-ridden Naomi is forced to testify against Mr. Cannon in court during her sexual harassment hearing when she feels she losing control of her ability to lie about it all. Meanwhile, Annie tries to move on and forget her relationship with Jasper by hanging out more with Silver when they decide to purchase a '65 Ford Coupe for themselves, but when she and Silver drive past the scene of her hit-and-run, the guilt comes rushing back to haunt her. Dixon and Ivy continue to maintain their fake relationship and decide to take it to the next level. While Navid becomes uncomfortable about Adrianna's new romance with a girl, both Gia and Lila grow uncomfortable with Navid trying to start a friendship with Adrianna which leads to Gia cheating on Adrianna with her ex-lover Alexa. Elsewhere, Ryan continues dating Ivy's troubled mother, Laurel, who pulls him into her dangerous lifestyle of pot-smoking and free-love, while at the same time, Laurel wants to sign Adrianna to a recording contract, but wants her to leave her band first. Also, Liam receives a surprise visit from his estranged father, Finn, who was recently released from prison and has apparently been trying to go straight by opening up a local bait and tackle shop.

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. 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. Meanwhile, Liam and his father, Finn, reconnect and attempt to rebuild their relationship as Liam moves in with him. Navid and Dixon host an underground gambling party that results in Dixon quickly becoming out of control with betting and he ends up owing Teddy's father's bookmaker, Mark, a lot of money. Debbie reveals to Harry that her yoga instructor made a pass at her, which forces the two to finally discuss their recent problems. Annie, aware of her parents marital troubles, turns to Liam for support. At the end, Naomi gets an unpleasant surprise when her psychotic and revenge-seeking sister, Jen, returns to Beverly Hills, with her French husband in tow, where they announce that they are the new owners of the Beverly Hills Beach Club.

Teddy invites Silver over for dinner at his house so she can meet his father, but things doesn't go as well as planned when Spence openly disapproves of her. Meanwhile, Naomi finds herself at odds again with her sister Jen when she begins giving Naomi a very hard time as she continues her community service work at the Beach Club. Navid realizes he still has feelings for Adrianna after she asks for his help to write a song as she prepares a solo singing career. Also, Annie learns of her parents problems marital troubles and thinks that their marriage is doomed.

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. Without her credit cards, Naomi is too distracted to realize Liam is in need of support to deal with the departure of his father, so he turns to Annie for comfort. Despite Spence's suggestion, Teddy refuses to end his relationship with Silver, and the two decide to spend the night together. Ivy invites Dixon to spend the summer in Australia with her and Laurel, but the idea doesn't go over well with his parents. Harry and Debbie's problems escalate when she finds out that Harry has been hiding Dixon's gambling issues from her. Meanwhile, Jasper returns to resolve things with Annie.

In the second season finale, after spending time with Liam and seeing his bravery in confessing his theft to his parents Annie finds the courage to confess to her parents about her hit and run. Jasper gets jealous over Liam and Annie's new closeness and sets fire to Liam's boat, leading to a fight between Liam and Jasper. Naomi secretly reveals to Ryan that Jen's baby is his, and Ryan who is upset that Jen will not let him be in the baby's life drives drunk and ruins the school sign. Dixon and Ivy go through a rough patch after he tells her about kissing Silver, but the real disappointment comes when he finds out he can't go to Australia with her. Adrianna and Navid have a public reconciliation and Adrianna must make the decision of whether to go on a year long tour with Javier. Silver decides to leave the decision of whether Teddy can handle both a relationship and tennis career up to him, who is upset when he finds out that his father tried to bribe Silver to end the relationship. The episode ends with Naomi being taken advantage of by a certain teacher, and realizes the desperation of the situation because she has already falsely accused him of harassment before.