For the next mission, the Road Rulers must face off against the boy band O-Town in a mission on Catalina Island. The first part of the mission requires each person to parabounce off a cliff. The Road Rulers take the lead by several minutes as they enter into the main part of the mission, a sailing race from Catalina Island to San Pedro. The Road Rulers are not happy when O-Town not only catches up with them, but also passes them in their sailboat. The close competition causes the Road Rules team to lose their team moral and sportsmanship. This mission creates a new bond and appreciation for one another, as the Road Rulers face only one more week together.
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