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.

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 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.

Annie, now in a coma and fighting for her life during surgery after being shot, wakes up and finds herself in an alternate reality where she sees what life would be like if she and her family never moved to Beverly Hills. Annie discovers herself working as an actress in a summer stock theater in Kansas and engaged to her old high school boyfriend, Jason. Annie also learns that her parents got divorced anyway, but Dixon is living in California and is a successful rap star, but to her dismay, no longer keeps in touch with his family and is living a reckless life. Navid happens to be Dixon's manager who tries to keep him under control to protect his image. Annie travels to Los Angeles and meets Naomi who works as a real estate agent had she never won her trust fund back. Teddy is a successful tennis pro-player, but has still never told anyone about his real sexual orientation. Adrianna is a successful actress and Hollywood's "bad girl" having never quit drinking, drugs or partying. Silver is a cynical Internet blog writer who isn't close to anyone and has her own website of writing dirt on celebrities. Liam is revealed to be attending college but has problems with delivering drugs for Dixon as to pay off a debt he owns to his old school rival Ty.