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, but he goes overboard while teaching Vanessa. Out of nowhere, he gets his truck towed away and he also gets glasses.

Bryana accidentally walks in on Bernie getting ready for his bath. Vanessa is not happy when Bryana moves into her room. Bernie and Wanda decide that it may be time to remodel the house, much to the dismay of Bernie's wallet.

Bernie's sister announces that she and her fiance, Monroe (Cedric Yarbrough) are eloping to Las Vegas. Wanda offers to have the wedding at the Mac house.

Bernie and Wanda are not satisfied with Bryana's test scores, and decide to enroll her at Jordan's school. As a result, Jordan is depressed because the kids at school think he's a nerd.

Jordan wants to be more popular in school, so Bernie teaches him to gamble, but the trick soon backfires. Wanda's birthday is coming up, and Bernie searches for a rare cognac-colored diamond.

Wanda decides to enroll the kids in an organization that teaches social skills to young people, with Vanessa instantly making new friends, who manage to get themselves into trouble & in mall jail.

Vanessa's new boyfriend is 18 years old, and has a child by a former girlfriend; Bernie confronts Vanessa about her new boyfriend and gets under her skin about it; Bernie reveals to Wanda that he thinks Vanessa is having sex.

Bernie is happy that Vanessa has joined the Spirit Squad, until he sees the racey costumes and provocative routines. Jordan enlists Bryana and her friends to help him sell a product.

Bryana's birthday party results in a lawsuit after she bounces high in the moon house and accidentally sending the girl flying. When Bernie hears about this, he tries to find a way to prevent the lawsuit from happening.

When Jordan develops a crush on a girl, Bernie teaches Jordan how to be a "player". Vanessa wants to attend a hip-hop concert.

Bernie hires a personal assistant. WWE World Heavyweight Champion Triple H becomes the victim of Jordan's prank phone calls.

Bernie wants to encourage Vanessa's burgeoning musical talent. Guest appearance by Isaac Hayes.

Bernie feels that Jordan is ready to walk home from school by himself, but his walk home days are over after Jordan and his friends pick on a crabby neighbor. Vanessa has a wardrobe malfunction while swimming.