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- Ronnie puts together a surprise birthday party for Senate but her good intentions quickly turns into chaos when all the guests resort to bickering and nitpicking at each other. Among the sparks at the party, Lipschultz snoops into Harper's briefcase and reveals his application for headmaster at an opposing school, while Lauren and Scott grow closer together as she has her own issues after being called a perfectionist.
- Guber discovers the high school drum line's freshman hazing involves physical abuse; a student-produced TV documentary about Ronnie worries her; a father is sentenced to being handcuffed to his son for a week.
- Debbie Nixon's mother believes he daughter is having an affair with Danny Hanson. Meredith fears that Jeremy has tampered with her prosthetic hand, sending them to therapy where he reveals his feelings. Harvey is selected to give a speech on what teaching means to hi for a chance to win a $250,000 grant for the school. A student's photography assignment concerns Marilyn, and possibly social services and he police.
- Danny discovers Brooke making out in a parked car on school grounds with a man ten years her senior. Harry discovers his dungeon students apparently bullying weaker students, but not all is as seems. Harry subsequently challenges Scott to a debate between the dungeon students and the debate team.
- With Ronnie's help, students sue Harvey for his continued abuse of one particular student. Jamal Crenshaw is accepted to college with the help of a plagiarized essay. Guber starts dating Meredith Peters. Steven assigns the annual "Gun Lecture" to Marla with surprising results.
- A black man goes to see Harvey and tells him he's his son. Harvey doesn't deny knowing his mother. But he doesn't know what to do.
- Lauren and Marilyn investigate a student who seems to be eating her own hair. Danny is discovered having sent letters home to the "over-weight" girls in his class after he is punched by a girl who received one of these letters. Marla goes to Steven and Scott about this issue, asking that he be fired. Meanwhile, Scott and Steven are continuing to have personality conflicts regarding leadership. Jamal Crenshaw's brother, Amaad, murders a store clerk and soon after, Jamal confides in Harry. Harry takes it to Ronnie, a past lawyer, who believes that Jamal's best bet is to turn himself in. However, when he doesn't; Harry and Ronnie do. Later on, Amaad comes to visit Harry at Winslow High and when things get out of hand, Harry calls the police. But before he can give them any details, he is stabbed by Amaad three times.
- Mikki, an 18-year-old Winslow student, tricks Harper and the administration into allowing Just Eighteen, a racy Maxim-like magazine to come to the school to shoot provocative photos of her. Ronnie, who stumbles upon the shoot, pleads with Mikki not to pose for the magazine, saying it is a decision she will regret for the rest of her life. Meanwhile, back at school, a student approaches Guber with information that Meredith hit her with her prosthesis during an argument. Also at the school, one of Lauren's students has an emotional break-down. The breakdown was apparently brought on by stress, caused from Lauren pushing too hard.
- Ronnie catches a student performing a crime; two female students tell Marilyn about their sexual conversations online with an older man.
- Scott represents Harvey in court. Marla has a confrontation with Meredith Peters, whom she has dubbed "The Hook Lady." Ronnie's on-again off-again boyfriend, Matthew, tries to impress her class in the value of Shakespeare. The school newspaper continues to offer sexual advice. Steven's daughter is expelled from her private school and enrolls at Winslow.
- Staff and students at Winslow High struggle to get on with their lives after a number of tragic events.
- Steve is asked to be by the side of a former student, now on death row and scheduled for execution. Scott finds it difficult to keep Jeremy's secret from Meredith. Ronnie's class is disrupted by a student with ADD whose creative abilities are hampered by his medication.
- Ronnie Cooke quits her law firm and joins the faculty at Winslow High and is immediately assigned a class of remedial students. Meredith Peters, now outfitted with a hook for her missing hand, is working at the school as a teacher's assistant. One of Lauren's students, interviewing for admission to Princeton, reveals a medical condition she fears will keep her out of college. The teachers hold a secret meeting regarding recent actions taken by the school administration.
- One of Kimberly's female students develops an unhealthy obsession with the young teacher, Scott Guber's mother comes to visit. Harvey considers.
- Racial tensions heat up amongst the students. This opens the eyes of Steven and Marilyn about their opposing views on different topics.
- Security tapes of the girls' shower room are missing... with footage of Lauren on them. Marla sends her entire class to the principal's office. Anthony's hit list is found. Lauren and Harry break up.
- The faculty decide to have a staff talent show to lighten the mood at Winslow. Lipschultz asks Ronnie to sing a duet with him at the talent show but she convinces him that Marilyn is just waiting to be asked. Meanwhile Danny befriends one of his cerebral palsy kids and arranges for him to attend Winslow. The mood is severely challenged when a student finds a notebook with plans for a bombing and shooting spree at Winslow.
- Lauren invites Scott to the symphony, much to the concern of Meredith. A student "falls" down a flight of stairs, but whether or not it was an accident is unclear. Danny and Marla dispute the place of God in a public school. Concern continues to grow over Harvey's speech for the $250,000 grant.
- Life seems to be one big lawsuit for Principal Harper. First, Mrs. Walsh, who was fired for spanking her students, sues for wrongful termination. Then, after Harper suspends Sheryl Holt for offensive content on her website, she sues to get the suspension overturned. Lauren gets knocked out by a launched breast implant. While Marylin counsels the girl on her self-image, Lauren decides to let the boyfriend off the hook. In court, Lipschultz's testimony - on both the Holt and Walsh cases - is disastrous and results in two losses for the school.
- A student's mother complains about bus fumes to Steven. The tape of Lauren showering ends up on Sheryl Holt's website. Harry gets in trouble for knowing Tyronn was a murderer. Scott becomes Lisa Grier's co-teacher for her Shakespeare class.
- Danny Hanson comes home to find his fiancé in bed with another man whom Danny attacks and send to the hospital, landing himself in jail. Scott declines Meredith's invitation to spend the night. One of Lauren's students is close to signing a record deal which would mean dropping out of school. The sex advice columnist's identity of finally revealed.
- Attorney Ronnie Cooke, visiting speaker, witnesses a fight in Harry's class. To defuse the situation Harry suggests the boys settle their differences with a boxing match in the room, which of course lands him in hot water with Guber. Marla is offended by the invitation to be the faculty sponsor of a Fat Girls Club. Steven reprimands Harvey for insulting his students and Danny Hanson by admitting to fantasizing about some of his students.
- Lauren finds Harry hasn't told his friend about her. Six teachers resign and Marla must teach a class she doesn't know how to. Scott wins a contest to be a guest conductor with the Boston Pops and asks Marilyn out when she is too nice to him. Steven and Harry look for a missing teacher, only to find him passed out drunk in his home. Apparently, he deserted his class the previous November, leaving Lisa Grier to teach and nobody noticed or cared. Steven decides to let Lisa continue to teach, touching off a firestorm by faculty and parents alike.
- Winslow High School battles the war on drugs. Marla Hendricks has an altercation with a student and deals with the repercussions.
- Charlie Bixby (Dennis Miller) takes an unconventional approach when volunteering at a teen hot line; Marla decides to try in-vitro fertilization and asks Harper to be the donor; Carmen reveals a secret from her past.
- A student's illness rattles Senate, who is haunted by feelings of futility; a teen's eating disorder upsets Lauren, who is also unnerved by a website advocating anorexia.
- Lauren continues her relationship with Daniel. Marilyn finds out that Jeremy's mother is locking her son in the basement for punishment. Steven can't date a student's mother. Kevin punches an opponent in a debate.
- Scott and Meredith shop for a new hand. The school production makes an interesting change to Our Town. The writing of one of Harry's students concerns him. Brooke Harper gets her hopes up after seeing her divorced parents sharing a kiss after a night out as a family. Debbie Nixon receives disappointing news from the college of her choice. Scott discovers a secret of Jeremy Peters'. Ronnie is serenaded at the school Christmas pageant.
- Steven's remarks prevent Scott from getting a job as a headmaster. Lauren finds out Daniel is stalking her. Marla worries when a convicted sex offender asks a younger girl to the senior prom. Marilyn suspects Jeremy has done something to his mother. Anthony Ward is accused of threatening a girl who turned him down for the prom, prompting the superintendent to transfer him to another school.
- Ronnie witnesses an attempted rape, then receives a shock when she presses for legal action on behalf of the victim; Hanson tries to prevent a student from being expelled for drugs.
- Seven teenagers, including Zack, are killed in a drunk driving accident and the students and teachers, both, must face their grief. Ronnie takes it especially hard having been close with Zack. Brooke's best friend was also killed in the accident. Meanwhile, Harvey tries to convince the students that he was George Washington in a previous life.
- Peabody Award-winning examination of a volatile but crucial topic. Hanson leads his class in a discussion of the n-word, including its use by rappers and stand-up comics. Its very utterance causes Marla to lobby Harper for Hanson's removal.
- As Senate approaches the school grounds, he saves a student from being attacked by gang members. After numerous attempts, Harry finally manages to get the boy to reveal that he is a member of the Crips. Meanwhile, Harper grows even more suspicious about Lisa and Buttle's deepening friendship, so Guber takes the reins and alerts Lisa's parents about their daughter's rumored affair. In the midst of these crises, Lauren has her hands full trying to help an overweight female wrestler, Christine, cope with the loss of her boyfriend. After winning an important wrestling match, Christine addresses the audience and asks them to stop calling her "The Blob", even when it's supportive. They respond by chanting her name instead. Lisa Grier's father goes to Buttle's home and catches them about to have sex. The next morning, Guber gives Buttle a choice: Voluntarily resign or be fired in such a manner as he'll never teach again. Buttle resigns and is ordered to leave by Guber. Harper also rebuffs Buttle. Kevin Riley talk to Guber and tries to mitigate Buttle's actions and ends up getting fired immediately for not disclosing the affair sooner.