Tailoring, the development of health messages based on assessment of key psychosocial variables that influence a prescribed behavior, has been gaining ground as an effective health education approach. The efficacy of this approach is based on the assumption that increasing personal relevance motivates greater elaboration, which is an important precondition for persuasion. Little research has been conducted to tease out the direct effects of tailoring on message processing. This study examines the effects of a tailored health education site on participants' evaluations of and elaboration on health messages. A total of 151 teens were randomly assigned to explore a tailored Web site or a nontailored Web site on adolescent sexual health and decision making. Results of the experiment indicated a statistically significant main effect for condition (tailoring) after controlling for situational motivation and need for cognition, F(1, 148) = 4.467, MSS = 2.177, p < .05, partial η2 = .030. Further evaluations and implications for future research are discussed.