Cleveland Brown and Cleveland Jr. leave Quahog and take to the road. On their way to California, they stop in Cleveland's hometown of Stoolbend, VA, where he reunites with his old high school crush, Donna Tubbs. Cleveland, still in love with Donna, is determined to start a new life with her, even if Donna's kids aren't exactly angels.

Cleveland, wanting to make his new stepdaughter like him more, asks her to accompany him to the school's father/daughter dance. All goes well until Cleveland has a mishap with the family pet and ruins his chance.

Attempting to get Cleveland Jr more friends, Cleveland invites the neighbor kid over to the house. However, when he overstays his welcome, Cleveland has a rough time trying to get him to leave.

When Cleveland needs a new job, Tim hooks him up at Waterman Cable. However, when Cleveland becomes the top salesman, Tim is green with envy and wishes for bad things to happen to Cleveland.

But when Cleveland comes up on some bad luck and misfortune, Tim has a change of heart.

After Cleveland has "the talk" with Roberta, Cleveland Jr. becomes scared and takes a vow of chastity. Meanwhile, Rallo becomes a church greeter.

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

Cleveland celebrates his first Thanksgiving with his new family and discovers a surprising secret about Donna's Auntie Momma.

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.

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.

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 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 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.

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

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.

After Cleveland gambles away Roberta's college fund, Kendra discovers that Cleveland was actually cheated out of his money and recruits Donna and Arianna for a "Cleveland's Angels" mission.

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.

Cleveland takes a struggling rapper (Kanye West) under his wing and, together, they write and record a new hit single.

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.

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.

The Brown family spends Thanksgiving in Las Vegas.

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.

Donna, frustrated by her husband's laziness on the weekends, nags Cleveland to help her around the house and to do something more with his life. To prove to Donna he can be as charitable as her, Cleveland recruits his buddies from Quahog and Stoolbend to participate in the First Annual Charity Beer Walk. When Donna gets injured at the event, Cleveland has to take over the housework.

At Donna's suggestion, Cleveland and Rallo start spending more time together; Cleveland Jr. becomes jealous of Rallo and Cleveland's new relationship.

"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 is upset when Tim gets a promotion over him at Waterman Cable, so he tries to sabotage him. Meanwhile, Rallo takes advantage of Cleveland Jr. when he realizes that he thinks that Rallo's turtle can talk.

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 discovers a shocking secret about his wife & his best friend Terry.

Meanwhile, Cleveland Jr. tries to get Rallo to break a nasty habit.

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

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.

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.

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.

When Rallo and his pals Bernard and Theodore perform in the school talent show, their rap about fiscal responsibility is not well-received by their classmates. Meanwhile, after Cleveland gets his own cable-access television show, the reviews are less than positive so he takes some tips from the most successful daytime talk shows that appeal to women.

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 finds out who his real friends are.

When a storm hits Stoolbend, the Brown/Tubbs family tries to salvage what's left of their vacation. Meanwhile, Cleveland Jr. shocks everyone with a proclamation of his religious beliefs.

The crossover continues on Family Guy S10E02 Seahorse Seashell Party (II) and American Dad! S08E02 Hurricane! (III).

Cleveland and Rallo get scared at slumber parties, and when they come home Donna makes them spend the night in a haunted house to prove their bravery.

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.

Cleveland poses as a woman as part of his plan to get Donna to appreciate him more, while Rallo uses Cleveland Jr. and his baby harness to get revenge on a playground bully.

Rallo suspicions that Murray's new girlfriend is a gold digger are confirmed, but not before it's too late, and Cleveland finds a shortcut to working out and improving his body to impress Donna.

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...

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.

Cleveland tries to become more racially sensitive after Choni moves into the neighborhood, and Cleveland Jr. becomes jealous after he agrees to set up his new wife on a date with a classmate.

Donna dumps Cleveland as her partner in a dance competition in favor of Cleveland Jr., so Cleveland vows revenge. But things become awkward when Cleveland Jr. wants to bring their partnership to another level.

Cleveland and Rallo create a successful ventriloquist act, but their partnership falls apart after Cleveland takes all the credit.

Cleveland temporarily loses his hearing after a hunting accident but soon discovers a new way to gain Donna's affection, while Roberta decides to run for student body president against incumbent Cleveland Jr.

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.

Cleveland becomes jealous of Freight Train's relationship with Cleveland Jr., so he finds a way to get back at him. Meanwhile, Rallo buys a classic Mustang off the Internet and goes out joyriding.

Cleveland tries to win tickets to a Justin Bieber concert and gets labeled "The Whitest Black Man in America." He later discovers that his "whiteness" is the result of being partly raised by a white nanny.

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.

After Rallo's prank results in Cleveland Jr. Getting kicked out of the scouts, Cleveland launches an elaborate plan to teach him a lesson.

Cleveland takes Roberta on a recruiting trip to his alma mater so that he can go to homecoming and relive his glory days, while Cleveland Jr. tries to find a replacement for Larry the Leopard.

Cleveland Jr. pretends to be Christian to get a beautiful girl, but soon discovers that he has an equally deceptive competitor. Meanwhile, Cleveland and Donna lie to a disabled veteran to spare his feelings.

Cleveland tries to redeem himself in the eyes of his son and family after an embarrassing toilet accident, and Rallo finally becomes tall enough to ride a roller coaster.

Cleveland's plan to bring in an actress to play Donna's long-lost mother backfires on him, but actually brings Donna's real mom out of hiding.

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