Alcohol use and risky single occasion drinking are common among adolescents and are associated with a higher risk of various negative social, physical, academic, or sexual consequences. Studies have shown that among college students, willingness to experience negative consequences is associated with a higher likelihood of experiencing these consequences in the future. However, it remains unclear how experiencing negative consequences influences adolescents’ willingness to experience them again. Based on a representative sample of 1,333 alcohol-using 14- to 15-year-olds (47.9% female), a path model was used to examine the associations between risky drinking, negative social and physical consequences, and willingness to experience the specific consequence in the future. As hypothesized, more frequent risky drinking was positively associated with experiencing negative consequences (i.e., saying or doing embarrassing things, regretted sexual experiences, impairment of schoolwork, problems with parents/friends, accident or injury, hangover, vomiting, memory lapses). Contrary to our second hypothesis, adolescents who experienced a negative consequence were also consistently willing to experience it in the future. Findings suggest that adolescents may see the experience of negative consequences as a necessary evil to attain the positive consequences. Prevention efforts may benefit from focusing on ways of attaining positive consequences by promoting alternatives to engaging in risky drinking practices, as well as reducing negative consequences (e.g., by promoting protective behavioral strategies).