Roberta and Rallo have a surprise for Lacey, Roberta’s wealthy rival. Meanwhile, Cleveland Junior learns responsibility while working at The Stool, but when he starts making changes to the guys’ hangout, a feud erupts between father and son.

Cleveland and Donna get mugged at an ATM and Cleveland gets shot, and the media makes it seem as if he was a hero. Meanwhile, Roberta convinces Rallo that she might be dying of a terrible disease and makes him do her bidding.

When Cleveland is diagnosed with high cholesterol, Donna puts him on a new high-fiber diet, which causes an intestinal backlash. It may stink up the place, but Cleveland quickly realizes his gas might score him a few points in the Broken Stool's karaoke contest. Meanwhile, Quagmire pays a visit to Stoolbend to deliver Cleveland some upsetting news.

Cleveland finds out that Cleveland Jr. will inherit all of his ex-wife's belongings and that his parents, Cookie and Freight Train, plan to remarry. To add insult to injury, Freight Train dumps Cleveland as his best man in favor of Donna's ex-husband, Robert.

After his confidence is shattered, Cleveland plans a family vacation to Africa.

Cleveland Jr. tries to become a "cool kid" and attend a Halloween party, when he is told he is too old to trick-or-treat. Meanwhile Rallo eats too much candy.

Coach Cleveland gets greedy to win the high school baseball state championship game and turns to cheating when his star pitcher goes out for the season.

Cleveland Jr. and Kendra, ashamed of their appearance in a swimsuit, feel left out of the fun when the family spends an afternoon in the pool and petition to pass a bill to grant equal rights for those who are overweight. Disgruntled by their defeat in the polls, Junior and Kendra flee to Wisconsin, a land where they feel more free and accepted, and Cleveland and Lester vow to bring them back to where they belong.

"How Do You Solve a Problem Like Roberta?" is the eleventh episode of the second season of the American animated television sitcom The Cleveland Show. It aired on Fox in the United States on January 16, 2011. The episode had guest appearances by Wilmer Valderrama and cast members of the show Glee.

In this episode, After Cleveland criticizes her parenting skills, Donna lets him deal with Roberta by himself. This episode came in third with 5.5 million viewers beating American Dad! and Bob's Burgers.

After Cleveland fights to save the town’s drive-in movie theater, his efforts to preserve the town’s history is noticed by the Stoolbend Preservation Society and he is invited to attend a private dinner party at the home of the great-great-grandson of the town’s founding father.

While at the event, Cleveland learns of the town’s legacy and decides to take back his beloved town.

When Cleveland sees all of his childhood possessions around town, he learns that his parents, Freight Train and Cookie, have been selling his stuff to get money after being scammed out of their life savings. Together, Cleveland, Freight Train and their friends get together to bring down the con man who targeted their family. Meanwhile, Rallo gets a toy Mr. Microphone and tries his hand at being a commentator, announcer and stand-up comic