The Wilson family arrives in Beverly Hills, after Harrison "Harry" Wilson takes a job as the principal at West Beverly High School, while his children, Annie and Dixon, attend the school during their first week much to the awkward circumstances of their father watching over them, while Harry and his photographer wife, Debbie, also keep a close eye on Harry's washed-up, alcoholic, actress mother, Tabitha. For Annie and Dixon, the school is one big culture shock for Annie, a sweet and friendly girl with a passion for the theater, and Dixon, a star athlete and scholar who was adopted by the Wilson family after they took him in as a foster child. Annie and Dixon have a close sibling relationship, which they'll need to help them cope with all the new cliques and classmates, including Naomi Clark, a hot and stereotypical spoiled rich girl who believes that money buys everything; Ethan Ward, Annie's former boyfriend from Kansas who's now Naomi's boyfriend, and a popular lacrosse star whose abilities rival Dixon's; Navid Shirazi, an aspiring student reporter who heads up the school's daily TV newscast; and Erin Silver, a rebel and wanna-be socialite who produces and stars in a YouTube-type video series, and who develops a crush on Dixon. Adrianna is a fellow student and theater "goddess" who is Naomi Clark's best friend... and Ethan Ward's secret girlfriend, and who has a serious drug addiction; George Evans is an arrogant West Beverly High student, who takes an instant dislike to Dixon because of his race (Dixon is black). Wendy is "sexy vixen" student at West Beverly Hills High who takes every advantage of her looks; Ty Collins is another student and theater major. Even the faculty seems hip and sophisticated at the school whom include the smart and funny teacher Ryan Matthews, beautiful guidance counselor Kelly Taylor, and successful theater actress-turned-high school-musical director Brenda Walsh. The Wilson family has just begun to realize how much their lives are about to change.

Naomi finds herself in trouble when she fails an assignment, and Ryan and Kelly bring the issue to Harry's attention, while Harry struggles with a disturbing revelation about the result of a secret tryst with Naomi's mother, Tracy, from many years ago. Meanwhile, Dixon learns more about Navid when they team up to try to pull a school prank against Palisades High. Annie meets a potential love interest in the form of drama student Ty Collins, who turns out to be the wealthiest student at West Beverly, and who spirits her away for San Francisco for the evening. Silver posts the story about Ethan's infidelity with Naomi on her Internet blog, while Adrianna continues her self-destructive slide into drugs and debauchery. Also, Ryan tries to ask Kelly out on a date, but she has to find a babysitter first for her four-year-old son, and former West Beverly alumni Brenda Walsh, now a successful Broadway and London theater director, arrives back in town to help put on a new school play.

Dixon and Annie find their Friday night plans disrupted after Debbie and Harry plan a family bowling night without consulting them. So, Annie plans to sneak out of the place to meet with Ty to attend a rock concert, while Dixon plans with Navid and Ethan to sneak him out so they can watch a movie at Navid's house. Meanwhile, Naomi has an unpleasant evening with her estranged and selfish businessman father, Charles, who puts her off for work. Also, Dixon invites Silver over to the Lucky Strike Bowling Alley, and he later finds Silver asleep in his car. Silver then confides in Dixon about her troubled home life and how her drunkard mother, Jackie, verbally and physically abuses her. The news gets back to Kelly who confronts Jackie about it, while at the same time, Kelly continues to be sought after by Ryan who tries asking her out on a date.

Annie and her parents, Harry and Debbie, are surprised to learn that West Beverly's theater director can no longer oversee the school musical. Tabitha offers to direct the musical play, but her eccentric and demanding attitude does not sit well with Annie or the other actresses. Kelly persuades Brenda to take over as the play's director, much to Tabitha's chagrin. But Kelly and Brenda end up continuing to argue over Kelly's continuing involvement with Ryan and taking up time with Kelly's son, Sammy. Meanwhile, Dixon tries to get a part time job at the Peach Pit coffee shop to get money to pay off a bully after Dixon accidentally dents the bully's car. Naomi becomes more distraught over her parents, Tracy and Charlie's, open-marriage arrangement, and she eventually confronts her father's mistress to show her true anger towards her. Elsewhere, Annie's growing relationship with Ty is the talk of the school, which leads to Ethan, who's growing more uncomfortable and jealous, to try to get her attention.

As opening night for the school play nears, Harry catches Annie kissing Ty, which makes him worry that she and Ty are moving too fast with their growing romance. Silver, stressed out from her job as the stage manager, gets some comfort from Dixon. Meanwhile, Naomi tries make her mother and father get back together, but Tracy's mind to divorce Charlie is made up. On the opening night of the play, the star Adrianna's drug use comes to surface from being under constant pressure from her overbearing mother, Constance, and when Brenda discovers this, she replaces Adrianna with Annie in the lead alongside Ty. But when both Brenda and Kelly confide in Constance about her daughter's drug abuse, Constance (a secret drug abuser-in-denial herself) refuses to believe them. Afterwards, Adrianna successfully gets her revenge when she manipulates and breaks up Ty and Annie's romantic get-together at a celebration party at a local hotel.

Adrianna and her evil-witch-mother, Constance, plot a cruel revenge against Annie and the rest of the faculty at West Beverly whom they think cheated Adrianna out of her role in the school play. Debbie's boss, Antonio, offers her a job to shoot a fashion show for Nylon Magazine during Fashion Week, where Annie uses the opportunity to her advantage for a class assignment, while her father advices her to try to make amends meet with Adrianna in order to try to catch her in the act with her substance abuse. Naomi believes the upcoming fashion show could help her parents' marital problems and she plans with Ethan to try to break up her father and mistress and have her mother, Tracy, meet with Charles, but it only makes matters worse. Ty and Annie's relationship is put to the test because of Adrianna's meddling. But when Adrianna lets her guard down and reveals to Annie that she lied about hooking up with Ty to break them up, it results in Annie declaring war. Silver is pursued by Debbie's sleazy client, Tony, to work in modeling, while a jealous Dixon becomes aware about what's going on, while Navid feels like he's the 'third wheel' to Dixon and Silver's growing romance. Meanwhile, Kelly receives a phone call from Sammy's father that could change her relationship with Ryan when she's offered to move to Wyoming to join Dylan, while Brenda, with her work at West Beverly finished, plans to return to New York.

As Silver's "half birthday" approaches, she decides to spend a spooky evening by watching horror movies with her friends at the famous Hollywood Forever Cemetery. But Dixon is not eager to attend when he reveals to her that he does not watch horror films. Meanwhile, Harry's past returns to haunt him when Tracy reveals she is searching for their long-lost illegitimate son. Annie and Ethan are paired up for an assignment, which leads to a possible romantic connection after the two take care of a baby. A mysterious new student, named Kimberly MacIntyre, arrives at West Beverly which considers with a police raid on the school searching for narcotics which leads Naomi to cover for Adrianna when Naomi takes the fall by taking her cocaine stash. After Naomi confronts Adrianna over her escalating drug addiction, she agrees to come forward to clear Naomi, but Adrianna soon goes back on her word when she lands another acting role which could jump-start her acting career and make her difficult-to-please mother proud. Also, Ryan seeks to explore his horizons since his breakup with Kelly by dating an attractive, but dim-witted actress.

After spending several days in the hospital recovering from a near-fatal drug overdose, Adrianna tries to make amends with Naomi. But Naomi refuses to forgive Adrianna for her betrayal. While serving her detention, Naomi meets a trouble-making punk, named Ozzie, who could spell trouble for her. Later, Adrianna makes a connection with Navid, who helps her through her situation as she's accepted into a rehab clinic. Meanwhile, Annie and Ethan finally take their rapidly growing romance to a new level during the school's annual homecoming dance, causing Naomi to feel jealous. Dixon asks Silver to the dance, but she turns him down for she feels, in her liberal and radical mind, that Homcomming is the scene of the morally corrupt. Ryan believes that the new student, Kimberly, is a narc after he sees her purchasing drugs. Also, Debbie confronts Tracy about the time Tracy kissed Harry.

Silver invites a few of her female friends over at her house for a girls' night, but the event quickly turns into a house party which causes massive damage to hers and Kelly's house. Meanwhile, Debbie and Harry finally reveal to Dixon and Annie that they have a long-lost, out-of-wedlock brother who was given up for adoption by Tracy Clark over 20 years ago. Dixon, who does not appear upset by the news, deals with the situation by talking to Silver about it. However, the news bothers Annie and she takes out her anger and frustration at Silver's party by getting drunk and being insulting to everyone. Annie and Ethan decide to keep their relationship a secret, while Naomi continues to hang out with the trouble-making Ozzie. Elsewhere, Adrianna and Navid continue to grow close until they have a misunderstanding. Also, a student sees Ryan and Kimberly kissing and begins to make demands to Ryan, while Kimberly is just determined to keep her secret identity under wraps at any cost and informs Harry about what's transpired between them.

Kelly arrives back in Beverly Hills and reveals to Silver what happened between her and Dylan during her trip. She also confronts Ryan, who has taken a leave of absence, about the rumors that he hooked up with a student, while Ryan refuses to explain his actions to Kelly or anyone else as not to jeopardize Kimberly's undercover status to nail the drug pushers at West Beverly. On Annie's 16th birthday, Naomi sees her kissing Ethan and decides to get back at her by inviting Annie's old boyfriend, Jason, to her birthday party hoping it will break up her and Ethan, who continue to debate over keeping their blossoming romance a secret... unaware that everyone around them already knows. Meanwhile, Adrianna has dinner with Navid and his large Iranian family and she also finds out that Navid is a virgin. At the end, the big twist comes when Harry's 22-year-old illegitimate son, Sean, visits the Wilson family for the first time during Annie's party.

Harry and Debbie welcome Sean into their home, while Dixon, Annie, and Tabatha welcome him awkwardly despite the fact that they don't know much about him, while Naomi and her mother, Tracy, welcome him to their home as well. Meanwhile, Kelly and Brenda's friendship is slowly fading away and gets wider after Brenda is hospitalized from an accident and confides in Kelly that she seduced Ryan weeks earlier. Naomi decides to hang out with a new group of girls at school despite Ozzie's advice that they want nothing to do with her. Also, Silver feels threatened when a cheerleader, named Christina, shows too much interest in Dixon who shares the same interests he does.

Annie overhears Sean in a suspicious conversation with someone over the phone, which raises her uncertainty about whether Sean really is who he claims to be. Meanwhile, Brenda tries to make amends meet to Kelly after confessing about a tryst she had with the departed Ryan Matthews. But Kelly and Brenda have to team up to accompany Adrianna to a group therapy session for recovering addicts where after she learns that a friend of hers is HIV-positive, Adrianna goes to a clinic to get tested, but receives some other potentially life-changing news. Elsewhere, Christina invites Dixon over at her house for a Gospel gathering where she makes a startling revelation to him which could shake his romance with Silver.

Adrianna reveals the secret that she's pregnant individually to both Naomi and Navid, who handle the news differently than expected. When Dixon reveals the depths of his feelings to Silver, their relationship takes a surprising turn when she reveals some facts about herself and that of her feelings of love. Meanwhile, Tabitha surprises Annie and Dixon with an unexpected belated Christmas gift of a car: which both Debbie and Harry disapprove of Tabitha trying to buy her grandchildren's affection after she also announces that she is leaving town to re-start her acting career with a job on a TV soap opera in New York. With a massive heat wave hitting the L.A. area, Annie and Ethan decide to to take a day-long escape to Tabitha's house Palm Springs for a romantic time alone.

Ryan Matthews returns to his job at West Beverly High which causes a mixed reaction for both Kelly, as well as Silver who finds herself writing a class paper on the book 'Heart of Darkness' to win back his trust after he rejects her from his class. Meanwhile, Annie decides to audition for the school's drama production of 'Antony and Cleopatra' and sets her sights on the lead, while she asks Ethan to audition for a role in the play so they can be closer together, while Annie also has a run-in with her one-time boyfriend Ty Collins. Adrianna becomes more uncertain about her pregnancy and refuses to deal with the problem. When her mother goes missing, Naomi is asked by her father, Charles, to move in with him and his mistress at their Malibu beach house which makes the situation very awkward and uncomfortable for everyone. Elsewhere, Silver and Dixon continue to experience bumps in their relationship which leads him to decide if he wants to end his romance with her.

Christina invites Dixon and Navid and the rest of the students to a house party where the band Carolina Liar will perform and Navid moves on from his relationship with Adrianna by connecting with a fellow Iranian girl named Nika. Meanwhile, Ethan gets involved in a traffic accident with a girl named Rhonda Kimble, a student at West Beverly whom he feels guilty about not knowing her since she's a long-time student. Adrianna and Naomi try to debate about how to tell both her mother Constance, as well as Ty, about Adrianna's pregnancy. While Ty takes the news very calmly, Adrianna fears a violent reaction from her selfish mother whom relies and takes advantage of Adrianna's acting career. But Adrianna finds out that Ty's parents want to bribe her to get an abortion and keep the news a secret. Eventually, Adrianna broadcasts a video announcement of her pregnancy to the entire school.

As Valentine's Day approaches, Adrianna's pregnancy now becomes the talk of the entire school as her 'baby bump' begins to show, while Navid continues to ignore her and grows more closer to Nika. Meanwhile, Silver asks Naomi for help in planning to make the best Valentine's Day ever for Dixon by setting up a dinner at the hotel where Naomi is now living at. But later, Dixon freaks out when Silver gets a much too permanent tattoo of their love to try to bring them back together. Also, Ethan's friendship with Rhonda continues to blossom which makes Annie very jealous, while she begins taking acting workshop lessons and tries to find her own motivation. But Rhonda begins using her medical condition to manipulate Ryan's too-trusting kindness to lead him more closer to her. Elsewhere, Naomi meets Liam Court, a bartender at the hotel in which they click romantically at once, but suspicion plagues Naomi as to whom Liam is when he does not want to talk about his personal life.

When Liam transfers to West Beverly, Naomi finds herself stunned but captivated by the intense, handsome bad-boy who takes her out on weeknights to partake in illegal street racing. Meanwhile, Annie drifts further apart from Ethan and spends an evening under the stars with fellow thespian Max. Annie also begins to suspect that Rhonda is not who she appears to be and also correctly suspects Rhonda of using her medical condition to play on Ryan's sympathies. Eventually, Ethan tells Rhonda that he's not interested in a relationship with her, but he breaks up with Annie over their differences. Elsewhere, Dixon begins to question his relationship with Silver, as well as her mental capacity when she makes a sex tape of them and shows it at part of her film project for Ryan's class. But it takes a turn when Silver finally reveals her dangerously disturbed personality when she breaks into Ryan's apartment and threatens him with physical harm.

Silver's struggles escalate and she reaches her breaking point. Kelly teams up with Ryan to look for her. Annie is forced to team up with Ethan and Naomi to search the school for Silver while Dixon is haunted by the problems of his past.

Donna Martin returns to Beverly Hills and pays a visit to her sister-in-law Kelly to talk about her life, while Kelly's relationship with her half-sister, Erin, becomes more strained over Kelly's over-protectiveness in her efforts for Erin Silver's mental recovery. Meanwhile, Dixon locates his biological mother and ask Annie's help to travel with him to Arizona to meet with her during Spring Break. Also, Naomi's infatuation with Liam intensifies when she goes on field trip with the class on Ryan's Habitat for Humanity house-building project while Ethan, wanting a change, becomes more acquainted with Liam who encourages him to embrace his own dark side.

Donna finds herself in a dilemma when she confides in Kelly during a night on the town that she must decide between returning to Japan and being with David, or moving back to Beverly Hills and keeping their 20-month-old daughter, Ruby, which leads her to decide to open up her own design shop in Los Angeles. Meanwhile, Silver is the topic of gossip at West Beverly due to her recent mental issues and does not know if she is ready to return to school. While Annie and Naomi try to patch things up between them in order to help Silver, Annie soon overhears that Naomi's father is being served a sexual harassment lawsuit, and she keeps it to herself... and later regrets it when Naomi is evicted from her hotel suite. Ethan continues on his downward spiral due to Liam's bad influence in wanting to be a bad guy as Liam is. Also, Adrianna and Navid meet with potential adoptive parents for the baby. Elsewhere, Harry and Debbie hold a yard sale when they finally sell their Kansas house and try to get rid of all of their old house's possessions as they plan to move out of Tabitha's house and to find a house of their own in Beverly Hills.

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.

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.

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.

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.

As Silver's "half birthday" approaches, she decides to spend a spooky evening by watching horror movies with her friends at the famous Hollywood Forever Cemetery. But Dixon is not eager to attend when he reveals to her that he does not watch horror films. Meanwhile, Harry's past returns to haunt him when Tracy reveals she is searching for their long-lost illegitimate son. Annie and Ethan are paired up for an assignment, which leads to a possible romantic connection after the two take care of a baby. A mysterious new student, named Kimberly MacIntyre, arrives at West Beverly which considers with a police raid on the school searching for narcotics which leads Naomi to cover for Adrianna when Naomi takes the fall by taking her cocaine stash. After Naomi confronts Adrianna over her escalating drug addiction, she agrees to come forward to clear Naomi, but Adrianna soon goes back on her word when she lands another acting role which could jump-start her acting career and make her difficult-to-please mother proud. Also, Ryan seeks to explore his horizons since his breakup with Kelly by dating an attractive, but dim-witted actress.

Silver invites a few of her female friends over at her house for a girls' night, but the event quickly turns into a house party which causes massive damage to hers and Kelly's house. Meanwhile, Debbie and Harry finally reveal to Dixon and Annie that they have a long-lost, out-of-wedlock brother who was given up for adoption by Tracy Clark over 20 years ago. Dixon, who does not appear upset by the news, deals with the situation by talking to Silver about it. However, the news bothers Annie and she takes out her anger and frustration at Silver's party by getting drunk and being insulting to everyone. Annie and Ethan decide to keep their relationship a secret, while Naomi continues to hang out with the trouble-making Ozzie. Elsewhere, Adrianna and Navid continue to grow close until they have a misunderstanding. Also, a student sees Ryan and Kimberly kissing and begins to make demands to Ryan, while Kimberly is just determined to keep her secret identity under wraps at any cost and informs Harry about what's transpired between them.

The Wilson family arrives in Beverly Hills, after Harrison "Harry" Wilson takes a job as the principal at West Beverly High School, while his children, Annie and Dixon, attend the school during their first week much to the awkward circumstances of their father watching over them, while Harry and his photographer wife, Debbie, also keep a close eye on Harry's washed-up, alcoholic, actress mother, Tabitha. For Annie and Dixon, the school is one big culture shock for Annie, a sweet and friendly girl with a passion for the theater, and Dixon, a star athlete and scholar who was adopted by the Wilson family after they took him in as a foster child. Annie and Dixon have a close sibling relationship, which they'll need to help them cope with all the new cliques and classmates, including Naomi Clark, a hot and stereotypical spoiled rich girl who believes that money buys everything; Ethan Ward, Annie's former boyfriend from Kansas who's now Naomi's boyfriend, and a popular lacrosse star whose abilities rival Dixon's; Navid Shirazi, an aspiring student reporter who heads up the school's daily TV newscast; and Erin Silver, a rebel and wanna-be socialite who produces and stars in a YouTube-type video series, and who develops a crush on Dixon. Adrianna is a fellow student and theater "goddess" who is Naomi Clark's best friend... and Ethan Ward's secret girlfriend, and who has a serious drug addiction; George Evans is an arrogant West Beverly High student, who takes an instant dislike to Dixon because of his race (Dixon is black). Wendy is "sexy vixen" student at West Beverly Hills High who takes every advantage of her looks; Ty Collins is another student and theater major. Even the faculty seems hip and sophisticated at the school whom include the smart and funny teacher Ryan Matthews, beautiful guidance counselor Kelly Taylor, and successful theater actress-turned-high school-musical director Brenda Walsh. The Wilson family has just begun to realize how much their lives are about to change.

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.

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.

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.