Despite sharing their first kiss, Nick and Elana decide not to date since they work so closely together. Then an attractive student teacher Heather Kellogg is assigned to Elana's class, and Nick asks Heather on a date. When Elana gives Heather a poor review, Nick assumes that it was because Elana is petty and jealous, and they argue. But when Heather is reassigned to Nick's class, he finds out that she is incompetent and deserved the bad recommendation. He apologizes to Elana. Meanwhile, during a class assignment they work on together, Tyler and Sarah become attracted. They kiss in private. However, they revert back to their usual adversarial relationship after the other students inadvertently find out and tease them.

Mezz wants to date Diane Fox, the school's sexy computer specialist whom he has known since they attended school together. Diane was never interested in Mezz because she is adventurous, so Nick vows to remove Mezz's inhibitions. Nick invites Mezz, Diane and Elana to dinner at a restaurant on top of a tall building. While the women are in the bathroom after dinner, Nick and Mezz climb out onto an overhanging gargoyle. Instead of being impressed, their dates have no idea where they went. Stranded, the guys must be rescued by a police helicopter. Meanwhile, when Fust rejects the students' ideas for the school newspaper, the kids revolt in pursuit of journalistic freedom.

Fust wants to impress the visiting school board chairperson, Mrs. Fleckner, so she will promote him to assistant principal. Meanwhile, to show that his students have a lot to learn from their elders, Nick invites the school's beloved old security guard Phil to tell the kids about his life. When Mrs. Fleckner visits Nick's classroom, Nick surprises Phil with a 73rd-birthday party. Mrs. Fleckner immediately tells Fust that if he wants to become the assistant principal he must terminate Phil because he is past the mandatory retirement age. Despite Nick's begging and a coordinated effort from the students, Fust refuses to reconsider terminating Phil. Then, at the board meeting where Fust is to be promoted, Nick and his students burst in to support Phil. Fust finally relents. During a romantic dinner, he convinces Mrs. Fleckner to promote Phil to security consultant--with no age limit—and hire a younger guard. However, Fust sacrifices his own promotion. Meanwhile, Nick and Mezz are afraid t

The school's band hosts a fund-raiser to earn money for new equipment. Everyone in the school gets involved recycling cans and donating the redeemed deposit money. Nick and Mezz relive their childhood as they compete to determine whose class can get more money for the band. Finally, when both classes end up with the same amount, Nick and Mezz decide to settle their rivalry in an unusual forum: a sumo wrestling ring. The match results in a tie. Meanwhile, Sarah wants to look like the other girls in her class, so she consults the popular Anna-Maria for makeup help—with surprising results.

Tyler's wealthy, divorced father wants to enroll him in a more prestigious school, but Tyler confides in Nick that he would rather stay where he is. When Tyler confronts his parents based on Nick's advice, they argue. Tyler moves into Nick's apartment, uninvited. He also asks his young friends to come over for a party. However, at the same time, Nick's apartment unexpectedly becomes the site of a wild bachelor party for Yaroker, who plans to marry a woman he impregnated while fighting in the Korean War. During the chaos caused by both parties, Tyler's father arrives and is outraged. Later, however, he realizes that Nick actually is a good role model. He allows Tyler to stay at the school. Meanwhile, Yaroker's fiancée decides that she would rather live in Korea with her teenage son than marry Yaroker.

When Nick scares the other teachers with a prank, they vow revenge. Later, Elana introduces Nick to her sexy accountant friend Suzanne Wilkinson, whom he quickly asks on a date. They have a great time. After a second date, Suzanne calls Nick incessantly and sends gifts. Nick becomes worried that she is obsessed with him. Elana informs him that Suzanne is afraid of commitment, so Nick should propose marriage to scare her away. Unfortunately, Suzanne accepts—to the delight of her brutish policeman brothers and priest uncle. Finally, everyone tells the terrified Nick that it was all a practical joke on him. Meanwhile, Sarah and Orlando agree that Valentine's Day is silly. They decide to kiss and find out why everyone thinks it is so great. After some overanalyzing and lack of confidence, they kiss--and discover they like it. Also, Tyler tries to find out who sent him an anonymous Valentine. And Tyler and Jared give romantic advice to a love-sick Davey.

Nick doesn't know the magnitude of his task when he tries to reform the worst student in the school, Harrison Schneck, whom Fust wants to expel. Nick takes the troublemaker into his classroom, and the situation becomes nightmarish. Out of desperation, Nick asks Yaroker for some unorthodox help. Ultimately, Nick allows the misunderstood Harrison to discover his natural aptitude for fixing things. Meanwhile, when the other students jealously taunt Orlando and Sarah for dating, the new couple fights back.

Nick's rapport with the students prompts Emerson to ask him to teach a seminar on human sexuality. However, Nick encounters trouble when the kids' desire for a frank and honest discussion conflicts with the strict guidelines of the school district. In particular, Tasha craves advice because her boyfriend Trey is pressuring her to have sex with him. Nick closes the door and tells the students what they need to know. Later, Tasha's parents mistakenly think that Nick has told Tasha that it's okay for her to have sex. But Tasha and her boyfriend actually listened to Nick's advice to wait. Meanwhile, Miles is grateful when Marco defends him from a school bully. But when Miles later purposely seeks out a confrontation with the bully, Marco refuses to help Miles, teaching him not to take advantage of a favor.

Nick's former geometry teacher Mr. Farb is hired to teach at Gerald R. Ford High School. Still remembering the constant verbal abuse he suffered in Mr. Farb's class, Nick defends Jordan when Mr. Farb chooses him as his new class victim. However, Farb easily outwits Nick by gaining Emerson's favor. Meanwhile, Sophia and Tasha must build a birdhouse for Yaroker's class. Sophia convinces Marco to construct the project for them, but Tasha believes that girls are just as capable at carpentry. When Sophia sees Marco's handiwork, she agrees.

Although Sophia's wealthy new boyfriend Michael seems to be the perfect guy, he always takes her to places where he knows she won't meet his friends. Fearing that he is ashamed of her background, Sophia convinces Michael to bring her to a party hosted by his friends. For emotional support, Sophia brings Marco, Miles, Jordan and Tasha. When Michael condescends to Sophia's friends, she realizes she no longer wants to date him. Meanwhile, Nick becomes so mesmerized by an expensive cashmere jacket that Mezz agrees to charge it to his credit card if Nick promises to return it within three days -- not realizing that the jacket has a magical quality that no one, not even Yaroker, can resist.

When Nick meets Samantha, the sexy maintenance supervisor of his new apartment house, he purposely breaks things so he can see her when she comes to fix them. However, his attempts to start a romance may cause trouble when he realizes that he is overburdening Samantha with his requests. Meanwhile, Tasha dates Johnny, the star of the basketball team. Despite Johnny's persistent demands that she have sex with him, Tasha refuses. Rather than admit that Tasha ended the relationship, Johnny starts a rumor about Tasha.

Now that Nick is dating his maintenance supervisor, Samantha, who is also an artist, he jealously chases away a male model that Samantha intended to paint. She convinces Nick to pose nude for her instead. Nick is thrilled that the artwork is one of Samantha's best—but mortified to learn that it will be displayed at an art show that his students will attend. Meanwhile, Marco and Jordan team up to buy a car with some help from Jordan's father. However, problems occur when Jordan wants to share the car on a day when Marco wanted it all for himself.

After Jordan is robbed on his way to school, Marco advises him to be more confident. However, Jordan takes this advice too seriously when he buys a handgun. Meanwhile, Emerson bids on Nick at a charity auction. He must do whatever she wishes, and that means designing a school bulletin board. Luckily, Yaroker helps Nick. Since no one else will bid for Miles, Sophia and Tasha pay a tiny amount for Miles to do everything they order him to.

Sophia is ecstatic when photographer Byron Davis compliments her and offers to put her picture on the cover of a catalog. She immediately goes to Byron's studio and models a skimpy robe. Suspicious, Tasha has Jordan access the Internet, and they discover that Byron posts nude photographs of his models for a fee. Just as Byron demands that Sophia take the robe off, Nick and the kids burst in with the police. Sophia is disappointed about her failed career opportunity but grateful to Tasha. Meanwhile, after breaking Samantha's toe while practicing dancing, Nick feels guilty. He insists on doing all the repair jobs in the apartment building for her—with disastrous results. Also, Emerson disorients the staff by rearranging the faculty lounge.