Cleveland is upset when he finds out that Donna is still attending a single mothers' support group.

Cleveland and Donna are excited to have the house to themselves when Cleveland Jr. and Roberta go on a school trip to Washington, D.C., but a disgruntled Rallo will do whatever it takes to keep Cleveland and Donna apart. Meanwhile Roberta's partying gets out of control and Cleveland Jr. comes to her rescue.

When Cleveland fills in as Santa Claus at his office holiday party, he has one too many eggnogs and lets the truth slip about Rallo’s father.

After a nostalgic flashback to the glory days as his high school's baseball all-star, Cleveland visits his Alma Mater to find out there's no longer a team.

Principal Wally gives Cleveland one week to raise money to re-build the stadium before the season begins. Cleveland then steps in as head coach and dusts off his retired jersey in an attempt to convince Cleveland Jr. to play ball instead of joining the math club

In order to teach her an important lesson, Roberta's new teacher encourages her to alter her appearance. Unbeknownst to him, Cleveland Jr. befriends, and falls in love wit the disguised Roberta.

Coach Cleveland comes to the rescue of frustrated parents by taking a group of delinquent teens under his wing. With the help of Cleveland Jr., he creates a new club dubbed "The Crazy Eights," and hopes that it will keep the kids on the straight and narrow. However, he is soon mixed up in bad business, and only the "Crazy Eights" can help him out.

Cleveland and Donna go on an overdue honeymoon to New York City, however, Cleveland suggests bringing his friends from the Stool, much to Donna's chagrin, to help Coach McFall reunite with a woman from his past. Meanwhile, Roberta, Junior and Rallo stowaway on the trip.

Cleveland and Cleveland Jr. teach Donna and the kids their tradition of celebrating Black History Month. However, when Rallo learns about his heritage at school, he provokes Cleveland into a battle royale with neighbor, Lester.

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.

"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