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, 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 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.