The transition from high school to college offers adolescents more freedom that may result in increased risky sexual behaviors. This exploratory study examines sexual behaviors of freshmen. Half of participants completed a questionnaire during the first week of college and the other half during the last week of their freshmen year. Significant differences in sexual behaviors between the semesters and subgroups of students who may be more likely to engage in high risk behaviors are identified. The results suggest that freshmen need more effective targeted educational programming about the importance of condom use in preventing sexually transmitted infections (STIs) and pregnancy.