Cleveland is upset when he finds out that Donna is still attending a single mothers' support group in order to have a good time. Meanwhile, Cleveland Jr. runs for student council president with Rallo as his adviser.
Cleveland celebrates his first Thanksgiving with his new family, including his own parents Cookie and Freight Train as well as Donna's Auntie Momma who all make a surprise visit to shake things up in Stoolbend. However, the holiday gets complicated when Roberta and Federline decide to celebrate on their own, and Cleveland discovers a surprising secret about Auntie Momma that changes his impression of her forever
Rallo conspires to kick Cleveland out of his mom's bed so that he can have her all to herself, while Roberta blows off her job of keeping an eye on Cleveland Jr. while on a field trip to Washington D.C..
When Roberta's new teacher encourages Roberta to alter her appearance, Cleveland Jr. befriends the disguised Roberta and falls in love with her. Meanwhile, Cleveland comes up with an interesting new invention.
Cleveland takes Roberta on a belated honeymoon to New York, but Cleveland spends more time with his friends than her. Meanwhile, the kids try to sell a pilot to MTV, and Coach McFall tries to "rekindle a romance" with Tyne Daly.
Cleveland's parents announce they are getting married and moving to Stoolbend. Cleveland Jr., fresh off inheriting his mom's fortune, offers to pay for the wedding. But can Cleveland and Freight Train play nice and get through it?