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Barry Shadwell is a four-time Superbowl winner for the Pittsburgh Steelers that Cleveland discovers is living back in Stoolbend after a successful NFL career in "Ship'rect". Roberta perks up on hearing Cleveland discuss Barry at home due to his acting connections. When Cleveland finds out that Barry has a white step-son named Larry, he dreams of trying to hook Roberta and Larry up together. Meanwhile, Barry invites Cleveland to be his partner in the Floaterboat Race. Cleveland is forced to tell his friends he will be Barry's partner instead of working on their boat.
At Barry's house with Roberta, Barry suggests Roberta and Larry hook up together to watch her television audition tape in the bedroom together, a suggestion that Roberta flat refuses. At home, Roberta is outraged that Cleveland tried to exploit her and he apologies, suggesting that they try to make things up over dinner with Barry and Larry. Donna puts her foot down and Barry and Cleveland dine alone after Cleveland tells Larry that Roberta died. After dinner with several drinks, Barry drives Cleveland home and kisses Cleveland to his horror.
Cleveland is forced to try to explain to Cleveland Jr. that he isn't gay and later Barry arrives, claiming that he was just following "Prison Rules" month, clearly uneasy with what they experienced. Barry tries to shift the blame to Cleveland but Cleveland defends himself. They agree to forget the entire incident but Cleveland expresses reluctance to continue being Barry's partner. Donna sets him straight that he shouldn't let his fear of Barry's perceived homosexual advances stop him from being Barry's partner and Cleveland agrees to be Barry's partner again.
As the race gets started, a wind blows Kendra's Cheeze-Its overboard, causing her to dive after it and upsetting the boat crewed by the rest of Cleveland's friends. The same wind capsizes most of the other boat as well. As Cleveland and Barry struggle to hold their boat together, they are forced into a number of compromising positions, culminating in having to pass a rope between their teeth together. They manage to hold their boat together and win the race. Afterward, Barry agrees that things have gotten just too uncomfortable between the two of them and offers to move.