Gabriel Friedman "Federline Jones" is the boyfriend of Roberta Tubbs. He is a white guy, who acts like he's black, much to the annoyance of Cleveland. He sports a fedora and says "blap" a lot. He is very forgiving, as he's turned the brown eye to all of the many times Roberta has dumped him and cheated on him, and later asked to get back together with him. Meanwhile, he has never cheated on or dumped her.
- In "A Brown Thanksgiving", some homeless people stole his car, leaving him and Roberta stranded. So, he tracked down the homeless people and gets his car back. In the process, he learned the importance of family values and spent the rest of his Thanksgiving with his parents.
- In "Brotherly Love", Federline learned the importance of fire fighters, and started to thank them for their services.
- In "How Do You Solve a Problem Like Roberta?", he saved currently ex-girlfriend Roberta, after she was kidnapped by a speeding roadster named Diego. He risked his life to save her and ultimately get her back and he succeeded at this. He also revealed to her that got a love tattoo for her, even though it was against his religion. This made Roberta fall back in love with him, where they reconciled.
- In "Escape From Goochland", Federline served as the designated driver to Cleveland and The Guys. He also attempted to help Cleveland and The Guys, by stealing the popsicle stick statue of their rival town, Goochland.
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