After a gay kid at school gets severely beaten in the parking lot, Scott partly blames himself for stirring things up. Scott starts a Gay-Straight Alliance at Winslow. After a first poorly attended meeting, and the requisite outrage from parents, Scott goes to speak personally to each class. The second Gay-Straight Alliance meeting is much more successful, and the witness to kid's beating finally feels comfortable enough to talk to the police. With a nudge from her father, Brooke befriends Riley, a 12-year-old genius who attends Winslow. Riley watches the boy that she has a crush on start paying more attention to Brooke, while Brooke just uses him to make Russell jealous. Riley is too smart for her own good. Marylin finds a shy student, Aisha, singing to herself in the senior study room, and urges the girl to audition for the lead in the school musical. After freezing up during her first audition, Aisha take Marylin's advice on how to make herself more comfortable and blows everyone away with her rendition of "I Will Always Love You."

When Aisha doesn't perform well in rehearsals, Marla threatens to replace her, but Marylin defends her prodigy and practices with Aisha until even Marla is impressed. Unfortunately, Aisha's boyfriend J.T. doesn't like her spending so much time away from him and pretending to be in love with another guy, even if it's on stage. At first, Aisha refuses to quit when J.T. asks her to, but after they fight and make up, Aisha tells Marylin she's done with being on stage. The Mayor's office sends a consultant, Dave Fields, to helpf fix what's wrong with Winslow. Steven originally mistrusts the slick guy, but when Fields offers Steven the opportunity to promote one of his teachers to have another assistant principal, Steven jumps at the chance. Steven suggests Marla for the job, while Fields secretly has Ronnie in mind for the position. When Becky and Riley, as reporters for the school TV station, tape two teachers having an adulterous affair in a classroom, Danny lets them decide on their own whether or not to air the scandelous story. The two girls end up deciding to take the high road... sort of.

Danny's drug-addicted sister declares that she's going into rehab, and drops off her four-year-old daughter, Allison, with her unprepared brother. Allison brings out Claire's motherly side, while Danny tries hard not to get attached since he's been disappointed by his sister for so many years. Danny decides to drop off Allison with a relative on her dead-beat dad's side of the family, but at the last minute can't bring himself to do it and decides to take care of her himself. When Aisha's understudy for the school musical has to leave town, Marylin and Marla convince Aisha to take back her part. J.T. gets a job working on the sets to be closer to Aisha, and Marylin notices how controlling and jealous he is. Marylin urges Aisha to stand up for herself, and after J.T. causes a scene during rehearsal due to jealousy, Aisha chases him outside and angrily breaks up with him. He slaps her across the face. Ronnie becomes the other nominee for the assistant principal job. Marla performs poorly in her interview. Ronnie says she doesn't want the job, but Dave Fields encourages her, telling her she'd be great, so she gives it her all during the interview, and even Steven has to admit that she'd be better in the position. Ronnie becomes the new assistant principal.

Danny and Claire both find themselves becoming attached to Allison. Danny tries to be optimistic about when his sister gets out of rehab, and decides that he can keep an eye on both her and Allison in Boston. However, when Danny and Claire visit Joannie in rehab, they find out she's getting back together with Allison's dead-beat dad and moving to San Diego. Harvey has to take a test to be re-certified as a teacher and finds out that his retirement nest-egg has been lost in the failing stock market. Ronnie gets resistance from both the teachers and Scott in her new role as assistant principal. Dave Fields tells Ronnie he's interested in her more than just professionally, and Scott finally comes to his senses and makes peace with Ronnie, moving her into a real office instead of sticking her in the supply closet adjacent to his office. J.T. proposes to Aisha, and Marylin is horrified, realizing that Aisha's bruises on her face are due to J.T. Maryline opens up to Steven about her own past as a beaten woman, and Steven pulls J.T. aside to talk some sense into him. Aisha accepts J.T. proposal, and on the musical's opening night, Marylin tries once more to talk some sense into the girl. Aisha breaks things off with J.T. all together, and give an incredible performance on stage.

Two Winslow students are arrested for murder after they pay two homeless men to fight each other and one of the men dies. Ronnie gets sucked back into being a defense attorney, and relishes being back in the court room. She not only gets the charges reduced for the two boys, but she's offered a job as a lawyer again. Ronnie decides that she's a teacher now, and stays at Winslow. Danny and Claire throw a birthday party for Allison and invite Joannie to attend. Claire gets a little carried away and the party becomes a costume party with cotton candy, magicians, and ponies, held at Claire's parents' house in the suburbs. Joannie is furious that some other woman is giving Allison all of this magic and takes her daughter away in the middle of the party. Marla and Scott set up a sting operation to bust students cheating in Marla's class, and find that the students are being helped by a midget (sorry – little person) hidden in a locker. The midget, Taylor, an ex-teacher himself, apologizes to Marla and asks her out to dinner.

An awkward and nervous boy, William, runs for Student Council President, and Danny originally encourages him. But when William's mother worries about her son getting humiliated during the race, Danny realizes he might be encouraging William into something that would hurt him. William stands strong, even when popular blonde Becky Emerson decides to run against him with young genius Riley behind her. Surprisingly, it's Becky's kind encouragement that gives William the nerve to give the election speech of a lifetime, earning him a standing ovation from his peers. Winslow scores high on its standardized testing, and Ronnie gets most of the credit for her plan to teach to the test. Scott, jealous of Ronnie, decides to take over the dungeon, since the kids have lost their regular teacher and had their normal studies neglected in favor of a standardized test. Zach feels that Ronnie, who is being interviewed on TV and by newspapers, is pulling away and spending more and more time with Dave Fields. Dave tries to kiss Ronnie, and while she admits she's attracted to him, she says that she's with Zach. Zach loses his temper when Dave tells him that he put the moves on Ronnie, and hits Dave twice in the face in the middle of the school hallway. Marla goes out on some dates with Taylor, the little person. She is fascinated by his sense of humor and ideas about school reform, but realizes that she's not attracted to him and not ready to have a serious relationship with someone who gets stared at on the street.

Aisha's alcoholic father dies and leaves her sheet music that he wrote. Aisha finally puts aside the hurt he caused her and remembers the love. With help from Marylin, she sets words to the music and sings it at his funeral. Joannie leaves Allison with Danny while she has a job interview, but tells Danny she doesn't want Claire hanging out with her daughter. Danny finds drugs in Joannie's apartment and Claire urges him to consider filing for custody. After a confrontation with his drugged-out sister, Danny takes Claire's advice. Ronnie and Zach's relationship is in tatters, but she still tries to get him to apologize to Dave Fields to save his job. Zach, who has found Buddhism, refuses to apologize since he feels no remorse, but Steven convinces him to put aside his pride. Dave continues to pursue Ronnie, who says she need some time on her own for awhile. Marcie's class assignment to take care of a baby makes her terrified of her own impending motherhood. Ronnie and Scott work together to comfort Marcie, and help, without pushing her, to start the adoption process.

Scott finally feels like he's reaching the students in the Dungeon when he gets them to express their feelings about Shakespeare with rap. Ronnie takes over Scott's number crunching duties when Dave Fields hands over a severely slashed school budget. Scott is horrified with some of the cuts that Ronnie suggests, including firing Harvey, Zach, Colin, and Marla, and discontinuing the Dungeon. When Scott's most promising rap-student is killed in a shooting, Scott decides he needs some time off and says he'll help out the budget crunch by resigning. Against her better judgment, Marylin helps Aisha sign a deal with a skeevy record producer, but she makes sure that the teen has an iron-clad contract examined by Ronnie. After Joannie gets arrested for purchasing drugs, Danny makes another legal inquiry into getting custody of Allison, and his lawyer recommends he and Claire get married. Danny proposes to Claire, but after an initial misunderstanding, he makes it clear that their marriage will be fake and will be just for Allison. Claire chokes back her emotion and says that she cares for Allison enough to do that for her. After Danny thinks about it for awhile, he gives Claire a ring and proposes to her for real. Claire worries that she guilted him into it until he shows her the receipt for the ring. He bought it two months earlier.

Danny has lunch with Claire's dad to ask for his blessing and finds out from him that Claire has been engaged twice before. This revelation makes Danny question the marriage, but after a night of honesty, Danny realizes that he's just as spontaneous as Claire, and they go through with the impromptu courthouse wedding. Scott comes back to work at Steven's insistence, and he and Ronnie struggle to work together on the budget. Ronnie uses her wiles with Dave Fields to finagle Steven an invitation to a formal event where he can ambush the mayor in the bathroom, but Steven is unable to accomplish anything. Scott comes up with the brilliant idea of cutting all funding for varsity sports, and Steven happily goes along with it. Steven challenges others to protect sports, because he has done his job and protected academics. Whitney Houston is in Boston on business, and William, who is a huge fan of hers, has invited her to the Winslow High prom as his date. William thinks Whitney has accepted his proposition, but it turns out to be a prank by the other kids. Marla tracks down Whitney at a local radio station and personally delivers William's letter, and to her surprise, the superstar shows up. Aisha, who was scheduled to sing at the prom, hands the microphone over to Whitney. Steven tells Scott that Brooke got into Harvard.