Bernie installs security cameras to monitor the family's activities.

Bernie decides that 8-year-old Bryana is too old to be riding her bike with training wheels. She crashes, and a guilty Bernie volunteers to take her class to the museum. Jordan steals an old cast from the hospital and wears it at school to get out of gym class.

Bernie is hoping for some peace and quiet as he prepares for a performance that night, but he must deal with the kids when Wanda's business meeting runs long.

Bernie gives Vanessa driving lessons.

Bryana accidentally walks in on Bernie getting out of the bathtub and catches a glimpse of his ""privacy."" Bernie reprimands her and a few days later at parent night at Bryana's school, is horrified to see that she has drawn a picture of him naked in the bathroom with his privacy exposed. He then realizes that Bryana and Jordan are too old to be sharing a room and moves Bryana in with Vanessa. But Vanessa feels invaded and is not making it easy on her new roommate. Wanda and Bernie decide to add another room onto the house for Bryana but in the meantime, while they've got a contractor in the house, Wanda decides to redo part of the master bedroom as well.

Bernie's sister, Benita, is back in town and announces that she and her fiance are eloping in Las Vegas. Wanda offers the Mac residence as a wedding site, but has an ulterior motive- she's planning the wedding she never had. Excited at the idea of giving his baby sister away, Bernie is passed over when Benita ask their older brother Carl to do the honors.

When Bryana's standardized test scores come back and she is ranked in the 39th percentile nationally, Bernie and Wanda decide to pull her out of her current school and put her into Jordan's. But Bryanna is so far behind that they threaten to move her back a grade. Meanwhile Jordan is depressed because the kids at school think he's a nerd.Bernie tells him that he's not a nerd, but a ""smart man"" who can help his sister with her schoolwork and save her from being held back.

Jordan wants to fit in with the popular kids in school, and Bernie suggests that he try playing games with them. When asking them to fly kites doesn't work and he's dubbed ""Benjamin Franklin"", Jordan tries his hand at their game, poker, and quickly loses his lunch money. Bernie teaches Jordan how to play cards and he becomes a whiz. Meanwhile, Wanda's friend Cheryl makes Bernie doubt that the gift he bought Wanda for her birthday is nice enough, so he enlists the help of his neighbor,Carl Reiner, on a search for the coveted and rare cognac-colored diamond.

When Bernie disapproves of Vanessa's slacker friends, Wanda urges her and the other kids to join Jack & Jacqueline, a 70-year-old organization set up to enrich the lives of upper-class black youth that Wanda once belonged to. But when Vanessa and her new friends get picked up for shoplifting, they quickly see that these ""respectful"", ""well-mannered"" and college-bound youths aren't all they seem to be.

Bernie learns Vanessa has a boyfriend, Rahim, who is 18 years old, but when he discovers that the teen has a child, he hits the ceiling.

Vanessa's high school guidance counselor explains to the Macs that her good grades are not enough to warrant acceptance into a good college. Reluctantly, Vanessa boosts her extracurricular activities by joining the Drill Team, which pleases Bernie greatly - until he sees one of the squad's racy and provacative routines.Bernie launches a mean offense, getting the principal and PTA to intervene, but he grossly underestimates Vanessa's rebellious teenage ways.

Against his better judgment,Bernie throws Bryana a themed birthday party, complete with a blow-up ""moon-jumper"", which ends up being the scene of the ""crime"" after Bryana's new friend,Riley,breaks her wrist. Riley's parents sue Bernie, claiming that he is a negligent parent, and in turn, Bernie counter-sues for defamation of character. A whirlwind of lawyer battles begins, during which Bernie's parenting skills come into question.

When Jordan develops a crush on a girl, Bernie teaches Jordan how to be a ""player"" and get his girl.

Bernie is being honored at his high school in Chicago, but when Wanda mixes up the dates and Bernie misses the ceremony, he hires an assistant to help him, which offends Wanda. Meanwhile, WWE World Heavyweight Champion Triple H becomes the victim of Jordan's anonymous prank phone calls.When Bernie blows Jordan's cover, there will be ""H"" to pay.

Legendary soul and R&B musician Isaac Hayes makes a guest appearence in Bernie Mac's confessional, offering him advice on how to nuture Vanessa's newly unveiled musical talent.

Bernie feels that Jordan is ready to walk home from elementary school after noticing other kids in his class doing the same. Although Wanda feels Jordan is too young to take such a big step, Bernie sees it as a rite of passage. But when Bernie hears that a bully is beating up kids on their way home, he has a change of heart.