Objective: To examine how specific aspects of a hookup are related to feelings of regret among college students, and how these patterns vary by gender and college context. Participants: Freshmen and sophomore men (n = 92) and women (n = 283) from a Midwestern university and community college. Methods: Participants answered questions about their most recent hookup and feelings of regret. Results: Frequency of engaging in a hookup was similar across gender and college context. Men and women were more likely to regret hookups with strangers and when alcohol was involved. Women had fewer regrets when their last hookup occurred with a partner they had also hooked up with in the past than when the hookup occurred only once with that partner. University students reported more regret when the hookup occurred with a stranger, occurred only one time, and when alcohol was used, but this was not found for community college students. Conclusions: Future research should examine hookup experiences through a developmental lens.