Cliff was hard to fool in the beginning seasons, like when Vanessa tried to trick him into telling her what Theo's problem was and Rudy trying to get him to buy her three more dolls. Cut to the later seasons, Cliff was easy to play, like when Vanessa tricked him into letting her go to an adult party(Luckily, Clair just happened to call Cliff just as Vanessa was leaving and busted her). And, Rudy tricked him into letting her wear a short dress to a party in the Fall. Cliff called Clair to show her how pretty the dress was, and Rudy was busted.