First sex marks a significant transition for most adolescents, yet teens often report that it was unplanned. Seventy-four college students participated in exploratory focus groups about their first sex. Although initially asked whether their first sex was spontaneous or planned, many participants revealed evidence of forethought or anticipation, signifying a third option, anticipation. This study suggests that the development and timing of sexual health messages should build on the apparent, albeit often unacknowledged, planning and thought that accompany the transition to first sex. Specifically, during the time immediately preceding first sex, young people might be particularly open to such messages.