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- Season 1 overviewOct 23, 2000-May 21, 200122 episodesSeason 1 episodes1. Chapter One Oct 23, 2000
- Teachers at a Boston high school juggle their personal and professional lives.
- 2. Chapter Two Oct 30, 2000
- Harvey's battle over making a student wear a bra to class escalates.
- 3. Chapter Three Nov 6, 2000
- The superintendent (Debbi Morgan), who is looking to remove Steven Harper, visits.
- 4. Chapter Four Nov 13, 2000
- Lauren encounters two students engaged in a compromising situation.
- 5. Chapter Five Nov 20, 2000
- A freshman approaches Lauren for advice about contraception; Lipschultz leads sex-ed assembly.
- 6. Chapter Six Nov 27, 2000
- Harper struggles with the loss of a teacher; as well as the man's alleged relationship.
- 7. Chapter Seven Dec 4, 2000
- Guber dates an aggressive woman; Lauren and Senate's romance heats up.
- 8. Chapter Eight Dec 11, 2000
- A student puts Ecstasy in Lipschultz's coffee; Milton is attracted to a girl.
- 9. Chapter Nine Jan 8, 2001
- Police search in the school for a student who shot a man at a restaurant.
- 10. Chapter Ten Jan 15, 2001
- News of Buttle's relationship with a student hits school computers.
- 11. Chapter Eleven Jan 22, 2001
- Kevin wants to ask out Marilyn; Harper's shocked by a cheerleading routine.
- 12. Chapter Twelve Feb 5, 2001
- Harry rescues a student; Kevin and Guber have a confrontation; Lauren provides support to a student.
- 13. Chapter Thirteen Feb 12, 2001
- Kevin seeks legal help in the wake of a teacher-student affair.
- 14. Chapter Fourteen Feb 19, 2001
- Guber must find replacements quickly after six teachers quit.
- 15. Chapter Fifteen Feb 26, 2001
- Harper learns of another teacher-student scandal; Marylin is threatened.
- 16. Chapter Sixteen Mar 26, 2001
- Lauren's angered by a security camera; Guber feels uneasy about a student.
- 17. Chapter Seventeen Apr 16, 2001
- Harper confronts Senate about his knowledge of Tyrone's gang life.
- 18. Chapter Eighteen Apr 23, 2001
- Marla shows her students what life might be like without an education.
- 19. Chapter Nineteen Apr 30, 2001
- A student who once drafted a kill list threatens a girl who turned him down for a prom date.
- 20. Chapter Twenty May 7, 2001
- The daughter of Harper's new girlfriend becomes rebellious at Winslow High.
- 21. Chapter Twenty-One May 14, 2001
- Marla has concerns about a prom date between a senior and a freshman.
- 22. Chapter Twenty-Two May 21, 2001
- A father wants his home-schooled son to go through Winslow High's graduation.