When Cleveland is reunited with his former high school classmate, "Fatty Patty," who is now skinny, beautiful and still has a crush on Cleveland, Donna becomes extremely jealous and wary of Patty's motives for wanting to be friends with Cleveland. Patty turns out to be a little crazy, and after she tries to steal Cleveland's "essence," Donna goes on the hunt to stop her.

When Lester invests in Cleveland's beer truck business and loses his life savings, he is so upset that he decides to take his own life - or does he? Meanwhile, Rallo is tired of getting his hair cut by his mom and opens his own barbershop in the kitchen.

Holt admits to Cleveland that he wishes he had a special someone in his life. Determined to help his lonely friend, Cleveland introduces Holt to Jill (guest voice Fergie), a cat-loving redhead who ends up being more than a handful. Meanwhile, Cleveland Jr. and Rallo anticipate the “birth” of Rallo’s pet fish.

Rallo gives Cleveland Jr. tips on how to woo the girl of his dreams; Cleveland Jr. challenges her boyfriend to a rap battle.

To help pass time while posing in a holiday nativity scene, Cleveland tells his family his own version of one of his favorite holiday stories, "Die Hard." In Cleveland's version, when Waterman Cable Company is taken hostage on Christmas Eve by a group of terrorists, including Tim the Bear, Lester, Federline and Kendra, a barefoot Cleveland - wearing a tank-top much like the one Bruce Willis wore in the movie - must endure window-shattering shoot-outs and fist fights with his friends to save his wig-wearing wife, Donna, in a parody of the greatest Christmas blockbuster...

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 is uncomfortable when Cleveland Jr. begins dating a Mexican girl who is hotter than his wife. But things get even worse when he marries her to keep her from being deported.

After Arianna is rude to Donna, Cleveland seeks revenge by egging Arianna's house; when Cleveland starts seeking revenge on more people, things get out of hand and he's accused of a murder he did not commit.

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.

In an animation first, the episode offers the audience a behind-the-scenes look at the "filming" of the episode. When Cleveland and Donna attempt to celebrate their anniversary, their unruly kids and disruptive friends, including Donna's ex-husband, Robert, get in their way.

When Rallo's teacher forces him to spend the weekend at a retirement home to get to know the senior citizens during the holidays, he meets Murray, who teaches him about Hanukkah. In an attempt to rekindle Murray's holiday spirit, Rallo helps him escape, but when his new friend's health begins to suffer, Rallo has to bring Murray back to the home. Meanwhile, Cleveland trains for a boxing match against his bully of a father, Freight Train, which ends with some bumps and bruises.

"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.

Cleveland and Donna celebrate Valentine’s Day with a trip to Los Angeles after scoring courtside seats to the all-star basketball game. Caught up in the excitement, Cleveland gets rowdy and talks smack to the players from the sideline throughout the game. The basketball champs, feeling hurt, seek revenge by paying a surprise visit to Stoolbend and putting Cleveland in his place.

Cleveland and his friends prepare to enter Stoolbend's annual boat race as a team, but when Cleveland's celebrity idol moves to town, Cleveland makes it priority to befriend him. And when his new pal invites him to join his boating team, Cleveland is forced to make a difficult decision. Meanwhile, Roberta gets wrapped up in her dreams of being a superstar.

When Cleveland Jr. bonds with Donna's ex-husband, Robert, Cleveland becomes jealous that Jr. thinks Robert is so much cooler than him. In order to prove how cool he is to his son, Cleveland challenges Robert to a "Coolympics" competition.

Cleveland creates his own comic book superhero and takes the entire family to a comic book convention in San Diego, where he discovers that Donna was once the star of a blaxploitation film.

Cleveland winds up in rehab after he becomes addicted to energy pills. But when he leaves rehab to go on a cruise, he winds up being kidnapped by Somali pirates instead.

A hip-hop producer comes to Stoolbend after a video featuring Cleveland goes viral. But instead of signing Cleveland, he decides he wants Cleveland's life for himself.

Cleveland and the gang head to their rival high school for an annual football game; Donna's sexy Halloween costume lands her in trouble with the police.

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.

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.

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 finds out who his real friends are.

Cleveland feels like his life is over after Cleveland Jr. stands up to him and kicks his ass. Meanwhile, Rallo tries to not get caught after a hit-and-run accident with Kendra.

An image makeover helps Cleveland Jr. get a date to the prom, but his date thinks that he's a lesbian.