Billy defends his dad with Courtney. Jake confides in Ashley. Matt makes fun of the “Environmental Police,” while Brooke uses the cause for her own ends. Billy isn’t sure whether to be friends with Olaf. Dylan’s concert is cancelled and Billy is responsible. Ashley’s feeling sorry for Dylan makes Matt jealous.

Matt’s tension with the Coach worsens and, unlikely as it is, Matt tries to give Jake romantic advice. Olaf has a theory about Bart Simpson. Jake tries a new approach with Courtney. Brook pursues her ambition to be Student Council President. Ashley tries to help Matt but Matt hits a wall with the coach. The Party at Courtney and Billy’s ends with a shock.

There’s a need for damage control after the Party but Brooke still has her eye on the election. Matt and Ashley have different takes on his “falling down drunk.” Jake finally asks Courtney out and tries to help Ashley with Matt. Cyndi gives Dylan some advice. Ashley wants to help Matt but Brooke manages to get there first.

Ashley and Matt’s relationship is on the rocks. Matt loses his patience with Jake and their friendship is put to the test. Brooke pretends to sympathize with Ashley. Courtney rejects Dylan’s attempts to make up. Ashley cheats on a test and Brooke and Kelly are quick to rub it in. Billy gets back in with Dylan.

Everyone’s worried about Ashley and her parents are about to ruin her life. Brooke ramps up her campaign for Student Council President. To help matters, Kelly starts flirting with Dylan. Billy does a double take when Theresa takes an interest in him. Dylan surprises Billy with a major offer. Jake hasn’t given up on helping Matt. Kelly sets Brooke up for a fall. Dylan’s determined to build up his band.

Concerned about him, Courtney decides to spend some time with Matt. Chris argues with Dylan over Billy's talent at drumming. Matt's sister Erin and transfer student Janice both have trouble fitting in at Hillside.

Matt considers asking his basketball coach to let him back on the team. Brooke catches Matt accidentally reading Courtney's private letter. Chris spreads a rumor to Amanda about Billy's status with the band.

Dylan can't figure out why Billy is so upset with him. Brooke makes a new friend in Stacy. Arseman questions Courtney if there's something more between her and Matt than friendship. Erin wants to attend a sleepover. Dylan spots a familiar face at the Avalon.

Courtney tries to interpret Matt's intentions when he asks her to a movie. Gossip spreads when Dylan asks Janice over to his garage after school.

Ashley returns to Hillside, complicating things between Matt and Courtney. Billy struggles to ask Amanda out, but she questions his maturity.

Rising tensions puts Courtney and Ashley's friendship in jeopardy. Stacy offers Brooke advice on improving her reputation. Dylan and Chris decide to seek a lead singer for the band. Billy tries to impress girls by boasting about masculine feats.

Dylan talks Ashley into a singing audition. Brooke takes Stacy clothes shopping. Billy bats around the idea of asking Ashley out. Matt's past issues are brought back into question.

Dylan's band gets an audition for a gig, but they still lack a lead singer. Matt is suspicious of Dylan and Ashley's friendship. Billy asks Dylan for advice on impressing women. Janice confides in Courtney.

Dylan and Chris make an inappropriate bet. Courtney has a valuable stolen from her locker. Arseman badgers Ashley about an unintended comment made about Chris.

Janice remains under suspicion for the theft of Courtney's necklace. When Arseman discovers Dylan and Chris's bet, she decides to turn the tables on them. Billy attempts to woo Ashley with a gift.

Following the band's concert at the Avalon, Dylan and Chris overevaluate their performance. Brooke discovers a surprising secret that Amanda has been keeping.

With the true thief caught, Courtney tries to make amends with Janice. Roxanne advises Chris to drop Billy from the band. Ashley takes Chris's advice to heart.

Courtney looks forward to Jake’s return from China, but doesn’t know where she stands with him. Chris convinces Dylan to make a firm decision about Billy’s status in the band. Dave is concerned that Matt is taking up his old habits again.

New relationships are scrutinized amongst the students of Hillside. Billy deals with his emotions after being dropped from the band. Arseman angrily confronts Dylan and Chris over the decision. Jake approaches Matt about his recent behavior, but the encounter gets hostile.

Ashley is uneasy about Chris and Roxanne hanging out. Brooke aspires to audition for the band’s new lead singer. Matt’s friends decide to confront him about his drinking problem.

Erin is troubled about Matt’s departure to a substance abuse treatment center. Ashley feels guilty that she’s letting her concerns affect her relationship with Chris. After Brooke pranks Arseman over her activism, John and Stacy conspire to pull a prank of their own.

Courtney worries about Billy’s state of mind after hearing their father is remarrying. Dylan is not thrilled with Chris’s choice for the band’s new lead singer. Ashley’s friends speculate on her distant behavior. John tries his hand buzzer prank on the wrong person.

The students prepare for the school’s talent content. Ashley encourages Courtney to change her image. Brooke joins the cheerleading team to get Dylan’s attention. Billy’s attitude takes a turn for the worst when he begins to bully other students.

Courtney begins to question if her affection for Jake is merely platonic. Never having hired her, Dylan attempts to cut Roxanne from the band. Brooke misinterprets Dylan’s sarcasm as legitimate interest in a lunch date.

Courtney convinces Dylan to talk to Billy about his changed attitude. Arseman discovers Courtney’s lack of romantic feelings for Jake may not entirely be exclusive. Brooke seeks the vacated head cheerleader role, but the squad has a different candidate in mind. Chris capitalizes on an opportunity that Dylan is forced to turn down.