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

Cleveland is upset when he finds out that Donna is still attending a single mothers' support group, but soon discovers the real reason the ladies get together.

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

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.

In the search for a friend for Cleveland Junior, Cleveland accidentally takes in Ernie Krinklesac, Lester's son. After taking Donna's advice, child services becomes involved and Cleveland & Lester must get his son back.

Cleveland tries to win over his new kids.

After losing the house to Loretta in the divorce and becoming fed up with Peter's shenanigans, Cleveland decides to leave Quahog with Cleveland Jr. He decides to drive cross country to California pursue his baseball dreams but gets sidetracked in his hometown of Stoolbend, Virginia & by chance runs into his old high school flame Donna. Cleveland gets acquainted with Donna's kids Rollo and Roberta & Donna's friends, Holt, Lester & Tim (the Bear) as well as her ex-husband Robert.

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