Ashley remains absent from school after getting caught cheating and plans to transfer to private school. Courtney and Arseman plan a farewell gathering for Ashley.

Matt gets benched. Brooke brags to Kelly how she upstaged Courtney with Dylan. Billy can’t find anyone to talk to but Olaf. Courtney asks Ashley for advice. Matt tries to start a fight with Dylan. Matt hides a problem at school and Ashley confronts him. Courtney’s fantasy life flourishes.

Billy and Courtney wrestle with their parents’ issues. Ashley is torn up over her doubts about Matt. Jake tries to help Matt sort things out. Courtney’s not sure it’s good for Billy to be “hanging around Dylan.” Brooke blames her dirty tricks on Kelly. Courtney thinks she has a chance with Dylan.

Brooke checks out Matt who obviously belongs to Ashley. Dylan faces off with Matt. Sparks fly. Brooke tries to flirt with Dylan, but it falls flat and she’s back to plotting with Kelly. After Courtney hems and haws, she finally drops a bombshell on Billy.

Matt’s drinking raises new questions. Does Ashley dare confront him? Courtney and Billy compete for Dylan’s attention. But Jake’s in the wings wishing Courtney would notice him. Dylan’s upcoming school concert creates new tensions. Courtney surprises Brooke over at Dylan’s.

Matt and Ashley try to put the pieces back together while Brooke plots furiously. Olaf “dislocates” himself. Jake tries to get up the nerve to ask Courtney out. Matt finds Dylan talking to Ashley. Dylan lets Billy try his drums. Ashley is shocked to find Matt at the Avalon with Brooke.

Ashley leans on Jake for help with Matt but how’s he supposed to help. Courtney provokes a fight with Dylan. Cyndi and Olaf’s attempts to save the environment meet with a feeble response at Hillside. Courtney makes up with Dylan and she and Billy plan to throw a party. Naturally, Brooke tosses a grenade into the plans and Jake has to pick up the pieces.

Matt takes heat from Coach Williams. Theresa bugs Brooke. Courtney falls for Dylan. Brooke can’t resist sticking her nose in again. Jake wants desperately to tell Courtney how he feels. Now Theresa fantasizes about Dylan. Courtney and Billy’s parents make it final. Ashley makes a shocking discovery..

Courtney confides in Jake about her parents’ problems. Matt and Ashley are doing just fine until Brooke tries to stir up trouble. Trouble is brewing for Matt with Coach Williams but we’re not sure why at first. Billy’s sucking up to Dylan until Matt interrupts.

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.