As Steve is about to celebrate his fortieth birthday, he makes his students list their life goals. Steve finds a similar list he prepared 20 years earlier, only to discover he has achieved little of what he wanted. Meanwhile, as Steve learns Regina is dating multi-millionaire basketball star Jordan Maddux, a pregnancy test indicates Lovita and Cedric are going to have a baby.

Regina recruits Steve and Cedric to perform at a charity function to impress the snooty wives of her boyfriend's teammates, since she's having some trouble fitting in. Bullethead and Romeo join Lydia's new club, but their ideas on how to spend the organization's funds cause division among the group's members.

Steve, depressed and feeling jilted over Regina's impending nuptials, kicks his effort to get her back into high gear when he hears of their accelerated plans to elope. Meanwhile, Lovita tells Cedric to flirt with the female landlord of an apartment they want. Lydia discovers that she was adopted.

Steve takes over as principal when Regina leaves town for her wedding, but she returns early from her honeymoon with tragic news. Elsewhere, Lydia nags Romeo and Bullethead about letting her join them during senior skip day.

Steve tries to be a good friend and lets Regina stay with him in her time of need. Cedric's visiting Grandma Puddin' makes some soul food out of the cherished possession Regina's husband left her in his will. Romeo, Bullethead and Lydia steal Steve's briefcase and hold it for ransom after the teacher refuses to chaperone a class trip to an amusement park.

Steve handles the arrangements for the school's annual Teachers Appreciation Day assembly, angering Cedric, who usually plans the event. The acting principal then suffers from the stress of organizing the occasion and dating a younger woman.

Steve manages an all-girl singing group called Jail-Bait, and books a gig for them that he hopes will revive his own show-business career.

Regina and Steve get very chummy during a game of Pictionary that also starts a fight between Cedric and Lovita. Lydia takes offense to an assignment Steve gives his music class that requires them to report on their family histories.

Steve has a hard time relinquishing his duties as acting principal when Regina returns to school, creating tension between them. Cedric is in the doghouse after Lovita discovers he has a private savings account.

Steve conspires with his friends and students to attend a celebrity golf tournament and appear to be in school at the same time after Regina refuses to let him take the day off.

When Romeo's family departs for New York City, he moves in with Steve to finish the school year. A misunderstanding causes Regina to invite herself on a ski weekend that Cedric and Lovita had planned to take alone.

Steve and Romeo become rivals for the affections of a twenty-five-year old swimsuit model.

Steve and his former Hi-Tops bandmates learn that Lil' Bow Wow wants them to appear in his latest music video.

When their apartment is flooded, Cedric and Lovita need a new venue for their planned house party.

Romeo's mother visits from New York City. When Regina keeps hinting about her tenth anniversary as principal, everyone prepares a surprise party.

With her best friend’s wedding coming up, Regina is stunned to discover she won’t be the maid of honor. Steve tells his music class to write a new version of the school song.

Steve's friend Byron, a television producer, decides to make Steve the subject of a documentary identifying a celebrity whose fifteen minutes of fame has expired.

The annual faculty-student talent show brings out the worst in Steve, Regina and Cedric.

Regina agrees to go on a date with Steve's friend Clyde, but only if Steve joins them and a friend of hers.

Still depressed over her own disappointment years earlier, Regina delegates the planning of the Senior Prom to Cedric and Lovita.

Worried Steve and Regina will end up spending the rest of their lives alone, Lovita asks Cedric to help arrange a blind date between them.