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Adolescents' engagement in risk-taking behaviors is well documented. However, the role of the dental practitioner in helping teenage patients understand and avert those behaviors is relatively unknown. The aim of this pilot study was to assess dental students' familiarity with adolescent risk behaviors, comfort level in discussing adolescent risk behaviors with teenage patients, and ratings of the relevance of these topics in dental education. Of the 373 University of Florida dental students across all four years who were invited to participate in 2017, 151 (40.5%) completed the survey. Among these respondents, 66% were female, 53% were from an underrepresented minority (URM) group, 40% were above the age of 25, 53% were in their preclinical years of education, and 47% were in their clinical years. In the results, the males had higher levels of comfort discussing adolescent risk behavior topics than the females, and the non-URM students had higher levels of comfort than the URM students. The clinical students showed statistically significant higher levels of comfort and ratings of the relevance of adolescent risk behaviors than the preclinical students. This pilot study assessed these students' comfort in discussing adolescent risk behaviors with patients and their level of agreement about the relevance of those topics in dental education across groups (age, gender, minority status, and educational level). Future studies are needed to examine pre- and posttest changes following interventions aimed at enhancing students' knowledge and comfort in discussing adolescent risk behaviors.