The primary goal of this study was to experimentally investigate the theory of gender and power (Wingood and DiClemente, Health Education and Behavior 27:539–565, 2000) in order to better understand gender differences in condom use behavior. The influence of relationship power (equal or low), partner-type (serious or casual), and gender on difficulty implementing condom use was explored using experimental vignettes. Heterosexual, sexually active, undergraduate students from a private university in the United States (N = 203) indicated how “difficult” it would be to implement condom use in a variety of situations. Results revealed a significant main effect for power and partner-type, qualified by a significant three-way interaction. The consistency of these findings with the predictions of the theory and methodological limitations are discussed.