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Teenagers may engage in consumption behaviors that their parents may not approve of, as one way of asserting independence. Such behaviors may lead teens to attempt to deceive their parents about purchases. This research examined teens’ tendency toward such deception. The authors conceptualize deception as being related to the family communication environment and the shopping context in which it takes place. Some family communication environments may stifle open discussion of products and purchases, thereby encouraging teen deception. Moreover, certain patterns of family communication may socialize teens to focus on standards exogenous to the family that, in turn, lead to a greater propensity to deceive. Susceptibility to normative peer influence, the extent of television viewing, and teen materialism may partially mediate the effects of the family communication environment. Except for television viewing, the authors’ predictions are generally supported by the data collected from a sample of high school students.