Cleveland discovers that his parents plan to remarry and that his father wants Donna’s ex-husband to be the best man.
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 an undercover mission
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.
Rallo gives Cleveland Jr. tips on how to woo the girl of his dreams; Cleveland challenges her boyfriend to a rap battle.
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.
When Cleveland and Donna are mugged at an ATM, Cleveland is accidentally wounded in the tussle. By the time the story hits the local news, the attention goes to Cleveland’s head, but Cleveland’s version isn’t the whole story. Meanwhile, Roberta takes advantage of Rallo, who thinks that his sister is dying of a terrible disease
Cleveland and Donna road trip to the Big Apple for an overdue honeymoon, and to Donna’s dismay, Cleveland allows the Stoolbend gang to tag along to help Coach McFall rekindle a long lost romance. Although, when Tim finds himself in a compromising situation and Lester’s language gets him into trouble, Cleveland is forced to choose between his wife and his friends.
Cleveland tells Cleveland Jr. to get a job and he does—at the Stool. Meanwhile, Roberta competes with the rich girl at school (voice of Ashley Tisdale). Other guest voices include Kristen Wiig (Mrs. Stapleton), Ed Asner (Editor) and David Lynch (Gus).
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.
Cleveland takes a group of delinquent teens under his wing, to the thanks of their frustrated parents. He and Cleveland Jr. create a new club to try and keep the kids on the straight and narrow. However, things don’t turn out so well.