Hillside

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.

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.

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.

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.

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.

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 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.

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 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..

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.

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.

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.

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.

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.

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

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.

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.

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 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.

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.

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

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.

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.

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.

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.

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.

Brooke is excited about departing Hillside for Paris until she realizes what she’s leaving behind. Ashley and Matt are conflicted about their feelings for one another. Billy makes amends for his past actions. Dylan begins to regret his decision to drop out of school.

Dave receives acclaim for his performance during the play. Brooke intends to use Chris to get under Roxanne’s skin. When Dylan hears about Billy’s bullying, he decides to make an example of him.

Brooke is incensed when she believes a mean-spirited character in Courtney’s play is based on her. Courtney chooses to protect Ashley at the expense of Matt’s feelings. Dylan makes a rash decision about his future.

Dave wants to impress Stacy, while Courtney comes along with an opportunity for exposure. Billy turns his angst on David after he stands up for John. Courtney approaches Matt about going to Dylan’s gig as more than just friends.

Courtney seeks actors for a play she’s producing. While Dylan struggles with school, a music opportunity opens up for him. Brooke finds out that Stacy is running against her for head cheerleader. Courtney confesses strong feelings for a student returning to Hillside.

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.

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.

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 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.

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.

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.

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.

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.

Chris and Roxanne remain friends; Billy's parents fight.

Russ conceals his problem; Dylan is with another girl.

Dave and Stacy make up; Russ has leukemia.

Pepper is concerned about Russ.

Jennifer is jealous; Stacy ridicules Liz's poem.

Billy has a new stepbrother; Roxanne confronts Jennifer.

Matt prepares to move; Billy joins the football team.

Jennifer has a crush on Billy; Pepper scores a goal; Dylan returns to school.

Dylan and Ashley go out.

Relationships show strain.

Matt is depressed; Russ does Brittany's science project.

Dave and Matt reminisce; Arseman parts with Dylan.

Matt and Ashley break up; a new girl comes to school.

Dylan moves out; Chris confronts Billy.

Tensions arise about the triangle.

Jason gets revenge; Ashley and Dylan are attracted.

Relationships show strain; Ashley and Matt plan a party.

The couples solve their problems; Dylan gets his job back.

Billy and Dylan suspect each other.

Dylan is fired; Ashley and Matt break up; Dylan moves in with Matt.

Dylan and Arseman have problems; a theft occurs on Dylan's shift.

Dylan seeks work; Roxanne spurns Chris.

Roxanne and Chris' concert flops; Billy ridicules Jason.

Everyone consoles Arseman; Jennifer and Jason transfer to Hillside.

Matt and Ashley make up; Arseman's grandmother dies.

Couples disagree; Dylan is defensive about dropping out of school.