Cleveland, wanting to make his new stepdaughter like him more, asks her to accompany him to the school's father/daughter dance. All goes well until Cleveland has a mishap with the family pet and ruins his chance.

Attempting to get Cleveland Jr more friends, Cleveland invites the neighbor kid over to the house. However, when he overstays his welcome, Cleveland has a rough time trying to get him to leave.

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.

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

Cleveland is upset when he finds out that Donna is still attending a single mothers' support group.

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

Cleveland and Donna are excited to have the house to themselves when Cleveland Jr. and Roberta go on a school trip to Washington, D.C., but a disgruntled Rallo will do whatever it takes to keep Cleveland and Donna apart. Meanwhile Roberta's partying gets out of control and Cleveland Jr. comes to her rescue.

When Cleveland fills in as Santa Claus at his office holiday party, he has one too many eggnogs and lets the truth slip about Rallo’s father.

After a nostalgic flashback to the glory days as his high school's baseball all-star, Cleveland visits his Alma Mater to find out there's no longer a team. Principal Wally gives Cleveland one week to raise money to re-build the stadium before the season begins. Cleveland then steps in as head coach and dusts off his retired jersey in an attempt to convince Cleveland Jr. to play ball instead of joining the math club