The fifth-season opener marks Steve's impending 40th birthday as he laments getting older without achieving many of his goals, including a motorcycle tour of the country. Meanwhile, during the summer vacation, Regina meets and begins dating a professional basketball player on a trip to the islands, and the relationship may lead to something even deeper. Lovita discovers that all the queasiness she's been experiencing might be because she is pregnant.
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; and 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. Meanwhile, 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. His plans may be dashed when Regina's advice to the girls causes them to question their act.
Regina and Steve get very chummy during a game of Pictionary that also starts a fight between Cedric and Lovita. Elsewhere, 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. Meanwhile, Cedric's 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. Meanwhile, Ced tries to pitch another one of his get-rich-quick schemes, which he calls "Bro" Balls, (black golf balls) to the contestants at the golf tournament.
Romeo moves in with Steve after the teen's family departs for New York and the boy stays behind to finish the school year at Booker T. Meanwhile, a misunderstanding causes Regina to invite herself on a ski weekend that Cedric and Lovita had planned to take alone.
Steve finds romance with a 25-year-old swimsuit model, but is shocked when he finds out that Romeo is trying to woo the same woman.
The sitcom celebrates its 100th episode with this musically themed installment, which includes performances by R&B singer Ron Isley and rapper Lil' Bow Wow.
"When a storm leaves their apartment flooded", Cedric and Lovita need a new venue for their party; Cedric states that the apartment flooded due to them using spurs on the waterbed.
Romeo's mother visits from New York with news that she plans to leave her husband and start a new life in Chicago. Meanwhile, Regina hints that she wants her friends to throw her a party to celebrate her 10th anniversary as Booker T's principal.
Regina learns that she is not going to be a maid-of-honor at a friend's wedding after she thought she was a shoo-in. Meanwhile, after a critic declares performance artist Romeo out of touch with reality, the Hightowers' neighbor and student decides to be more like others so Steve tells his music class to write a new version of the school song for an assembly the mayor is attending and Steve and Cedric compete in a cooking contest.
Clips from past episodes are featured as a television producer interviews Steve's friends for a documentary about the former singer. 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. Cedric, Lovita and Regina seize the opportunity to be interviewed for the program and warm to the chance to see themselves on television. But when questioned, Regina won't divulge any information about he
The annual faculty-student talent show brings out the worst in Steve, Regina and Cedric. With the approach of the annual student-faculty talent show, Steve and Cedric are determined to find partners to help them to beat the defending champion, Regina. Though she feigns a lack of interest in the contest and its prize, Regina secretly scours the student body for someone who will help her win again. And upon learning Bullethead is performing with Cedric, and Romeo has been chosen for Regina's tap d
Romeo, Lydia and Bullethead sue Steve for damaging their pager and the case is heard on the Judge Mathis Show. Meanwhile, Cedric sends erotic e-mails to Lovita posing as a secret admirer, not realizing that she knows that the missives are from him. When Judge Greg Mathis comes to the school's Career Day, Steve makes the mistake of having the television courtroom judge's new Mercedes Benz towed from his personal parking space. Then, as Judge Mathis is making a presentation to his class, Steve con
Regina agrees to go on a date with Steve's old pal Clyde, but only if Steve joins them and escorts a friend of hers. Meanwhile, Lydia doesn't realize that the cheerleaders only want to hang out with her because she works in a hip clothing shop. - - - When Lovita gets a tattoo, Cedric strongly objects. Refusing to be drawn into the middle of a marital spat, Steve ushers them out of his apartment so he can prepare for a date. But when former bandmate Clyde arrives looking for some help in finding
Regina puts Cedric and Lovita in charge of planning Booker T's prom; Lydia thinks a boy she likes is going to ask her to the dance, but the teen has other plans. - - - Still depressed over her own disappointment years earlier, Regina delegates the planning of the Senior Prom to Cedric and Lovita. While Romeo looks to auction himself off as a date to the highest bidder, Lydia makes it perfectly clear she wants Arthur Rabinowitz to be her date. And with Arthur's help, Bullethead hopes his date wil
Cedric and Lovita secretly set Steve and Regina up on a blind date. Romeo and Bullethead send Lydia false college acceptance letters. Lovita suffers from mood swings. With two tickets for a Chicago Bulls basketball game in hand, Regina asks Steve to join her. Unaware of their plans for the game and 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. While Cedric struggles to understand why Lovita is suddenly s