Early sexual debut has been a focus of social scientific research due to its association with adverse circumstances and negative outcomes. However, there has been a recent shift to considering not only chronological age, but also the degree to which the event is viewed to be optimally timed (i.e., the perception that it occurred at the "right time" versus too soon). The purpose of this study was to assess how individual/family background variables and contextual aspects of the experience (including partner and relationship aspects) are associated with both the actual age at sexual debut and the perceived acceptability of the timing of the event. Using data collected from students at a U.S. university between 1990 and 2019 (N = 6,430), several factors (in addition to chronological age) were associated with the perceived acceptability of the timing of sexual debut. Strong gender differences were found - women perceived their timing to be less acceptable, even though they did not differ from men in actual age at sexual debut. Other robust predictors of perceived acceptability included (lower) religious involvement and recalling desire (for the experience), pleasure, and lower guilt at the time. Only slight changes occurred over the 30-year period in age at sexual debut and perceived acceptability of the timing. Suggestions for future research are provided and implications for sex education/sexual health interventions are discussed.