The Cleveland Show is a spin-off of the much-loved series Family Guy. The series features the adventures of Peter Griffin neighbor Cleveland Brown. He moves to his hometown in Virginia with his 14-year old son, Cleveland Jr. Many years ago, Cleveland was a high school student madly in love with a beautiful girl named Donna. Much to his dismay, his love went unrequited, and Donna wound up marrying another man. Cleveland once told Donna he would always love her, and if this man ever done her wrong, he'd be there when she called. Well, this man done her wrong. Donna's husband ran off, leaving Donna with a teenaged daughter and young son. Now she's open to Cleveland and offered him another chance at love. Unattached after the Loretta-Quagmire debacle and true to his word, Cleveland joyously unites with Donna, and he and his son move to Virginia to join their new family.
The episode starts out when Cleveland, who is reading the newspaper, but gets stopped by Rallo and Roberta's fighting. A while after, Robert comes by to get his alimony check from Donna, taken in cash. The kids fighting end up with Cleveland getting hit, then as Robert tries to leave, Cleveland stops him and says that if he still wants to get more alimony checks, he will have to take his kids for a day.
Cleveland and his friends prepare to enter Stoolbend's annual regatta, but when Cleveland's celebrity idol Barry Shadwell moves to town, Cleveland makes it priority to befriend him. Barry invites Cleveland to join his sailing team and Cleveland eagerly abandons his friends. Following a dinner out at which Cleveland gets very drunk, Barry drives Cleveland home and kisses him.
After a close call with bank robbers, Cleveland discovers that Donna knows very little about him. While killing time with the guys by attending an open house, Cleveland discovers he has a secret admirer. After tricking the real estate agent into revealing the name of the house owner, Cleveland learns it is Patty Donner.
After another day stuck in traffic, Cleveland hits on the idea of running a beer truck to dispense beer to those waiting in traffic. When Lester hesitates to invest, he decides to take the issue up with Kendra resulting in his being teased by the guys. Kendra shoots him down but he decides to invest their funds anyways.
After Cleveland learns that his friends own his old stuff, he confronts his father, who is selling his childhood items. Cleveland buys his stuff back, but Donna tells Cleveland that there is no room in their home for the items. He puts it all in a storage are, where he finds out his parents are now living. They explain that they were selling his stuff because a con artist took advantage of LeVar and they lost all of their money.