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.

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.

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.

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.