Navid and Adrianna fantasize about their future, but when they tell his parents about their decision to spend the rest of their lives together, things don't go as they planned when both Mr. and Mrs. Shirazi threaten to sever all ties to their son. Meanwhile, Silver tries to adjust to her new Catholic girls school, but soon learns that it is not all it's cracked up to be when her new school mate, Angela, gives her some advice to be honest about her past. Silver goes along with it... and later regrets it. While Dixon feels left out of Silver's life, Annie and the rest of the Wilsons are dealing with having Naomi as their new house guest. Naomi convinces Annie to go on a double date with Liam's friend, but Annie is shocked at the way the evening ends when Liam propositions to her. Later, Naomi's older sister Jen, who's just as brash and amoral as she, arrives in town for a visit. Naomi has no idea just how devious her sister is... and of her connections to Ryan as well as Ethan.

Following their engagement, Navid and Adrianna celebrate their respective bachelor and bachelorette parties. While Adrianna feasts with Annie, Naomi, Silver, and their female friends at the Wilson home, Liam takes Navid, Ethan, and Dixon to have a wild night on the town with some college girls at a burlesque club. Meanwhile, sparks fly between Ryan and Jen, and Dixon continues to feel unappreciated by Silver. Jen also persuades Naomi to stand up to their father as well as move in with her at a local house, while Naomi continues to grow more insecure as well as jealous over Liam when she sees him talking with Annie whom he sees as naive and holding back her own dark side.

As West Beverly prepares itself for the annual prom, Annie, Adrianna, Naomi, and Silver go out shopping together for the right evening gown to wear and try to get all glamored up for the event by visiting a famous hair stylist. A dateless Annie agrees to attend the event with the socially awkward Charlie, who has a massive crush on her. However, when he realizes that Annie is only interested in being friends, Charlie turns against Annie... showing his true repressed psychopath colors to plot a cruel revenge. Naomi attends the prom with Liam while she learns that Jen has emptied out her trust fund to support them living at Jen's new house. Meanwhile, Dixon is nominated for prom king, while Ethan learns that he has been accepted into lacrosse camp for the summer. Also, both Kelly and Harry take action to help Liam get on the right track, while he continues to try to temp Annie to embrace her own dark side as he has with his own. Ryan grows more closer towards Jen, and he also ignores Kelly's warnings that Jen is a devious, sociopath seductress whom is using him for self interest. At the prom, Harry informs the students in attendance that any after-prom activities will be dealt with punishment, while Navid provokes a fistfight with Ty when he reacts with indifference over the pregnant Adrianna's unborn child which is in fact his. When Silver learns that Dixon has nominated himself for prom king, she decides to enter for prom queen as a write-in candidate and finally gets to speak her mind to the attendees.

Adrianna and Navid are forced to make an impromptu exit from the prom when Adrianna goes into labor. Brenda Walsh shows up at the hospital to lend emotional support as Adrianna's labor gets more difficult. Harry and Debbie also turn up at the hospital with Kelly to lend emotional support to Adrianna when she decides to give her baby up for adoption. Across town, in defiance of Harry's orders not to throw any post-prom party, Naomi and Liam decide to throw a party in Jen's house, which she does not approve of. There, Dixon confronts Ethan about Silver when he notices that Ethan might be developing romantic feelings for his girlfriend. When Liam arrives late for the party, Jen takes advantage of his rebellious state. However, Naomi confronts and accuses Annie of seducing her boyfriend. Beaten up and humiliated, Annie leaves the party in a rage. Later, while driving home, Annie runs over someone with her car in a hit-and-run. Liam later decides to confess that it was Jen who seduced him and not Annie. He is unfortunately grabbed by parole officers and sent away by his stepfather to a military academy. Jen is left behind to claim herself as Naomi and everyone's savior... with no one suspecting her true nature.

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.

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.

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.

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.

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 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.

Naomi finds out she can now access the money in her trust fund, so she decides to throw a giant birthday party where The Honey Brothers perform a few songs. Dixon, Navid and Liam decide to take Oscar out for a night on the town, but their party ends when Ivy finds a Facebook photo of Dixon doing a body shot off a girl. Annie has an instant connection with Charlie, a guy she meets at a coffee shop, but seems more interested in exploring her relationship opportunities with Liam. Jen is forced to go on bed rest until she delivers the baby and has no choice but to allow Ryan into her life. Silver confronts Teddy about his drinking problem.

Silver, Naomi and Adrianna craft a plan to seduce Mr. Cannon and prove that he raped Naomi, but they underestimate his ability to control the situation. Teddy and Ian are forced to do manual labor as punishment for fighting. Dixon fears for his life and pushes Ivy away, leading her straight into the arms of Oscar. A pregnant Jen seeks to hire a new assistant and Debbie applies for the job.

New parents Jen and Ryan find out about Naomi's rape and Jen decides to take matters into her own hands. Ryan encourages Naomi to come forward even though his own job may be in jeopardy. Victor arranges a photo shoot for Adrianna and instructs her to go topless, while Navid and Silver watch in shock. Annie discovers that Charlie has a dark and disturbing side when she sneaks in to observe a staged reading of his play. Liam lands a job working shirtless in the window and on the sales floor of a clothing store. A mysterious customer offers him an opportunity he can't refuse. Dixon apologizes to Ivy for breaking up with her but doesn't realize that Ivy decided to lose her virginity to someone else. Oscar confronts Laurel and Ivy with shocking news about his past.

Adrianna has to un-invite Navid to her magazine premiere party after Victor arranges for her to go with Joe Jonas to boost her image. Annie and Dixon visit their dad but are shocked when a woman answers the door. A series of mishaps lead Jen to conclude that she is a bad mother, so she makes a decision with Ryan and her son's best interest in mind. Naomi and Ivy team up to seek revenge on Oscar with a plan that involves skinny-dipping in the Beach Club pool. Navid discovers that his father may be using underage girls in his porn films and convinces Silver to go undercover.

Annie convinces Marla to attend a Hollywood movie premiere of one of Marla's old films, while Ryan has an unexpected visitor and Teddy catches Marco in a lie and begins to wonder if he is being cheated on. Naomi finds out Max was accepted to a college in a different state, while Silver has a breakdown after receiving some upsetting news that causes Navid and Dixon to stage an intervention.

In an effort to put her inheritance to good use, Annie volunteers to organize a big charity fundraiser.

Naomi's sister Jen arrives with her son for a surprise visit. Adrianna and Dixon land a meeting with a major movie producer to discuss music on his next film, but are sabotaged by Vanessa. Meanwhile, Silver gets accepted into New York University and Ivy attracts attention in the underground scene when she switches to a less conventional style of art.

Naomi is convinced that Annie's new business partner P.J. is the perfect man for her, but discovers her sister Jen is also interested in him.

Dixon collapses while arguing in the recording studio with Adrianna. (guest stars include Manish Dayal and Robert Hoffman)