<p> The rate of individuals transitioning to old age (<i>i.e.</i> 65 and older) is expected to exponentially increase in the coming years (United Nations Development Division, 2015), and as such society&rsquo;s need for research promoting successful aging to meet the demand for this growing population is accelerating. The transitionary period into old age holds significant and diverse challenges and losses that interact across life domains, and can make old age seem depressing and lead to a decline in well-being (Stevernick, 2014). Although older adults have many challenges that are associated with old age, many continue to live in a positive and adaptive way (Jeste &amp; Oswald, 2014). As such, successful aging has become a highly researched model, which refers to relatively high levels of cognitive, physical, and social functioning, and distancing from disease and disability (Rowe &amp; Kahn, 1997). The purpose of the current study was to investigate whether higher levels of sexual frequency and sexual satisfaction as well as personality predicted successful aging. Successful aging was operationally defined through the change in overall psychological well-being from middle to older adulthood. Health status and gender were also assessed to see whether they moderated the effect of predictors on overall psychological well-being. The study employed previously collected data from the Wisconsin Longitudinal Study (WLS), a large sample of Wisconsin high school graduates who provided longitudinal data on diverse information across an extensive period of time (Herd, Carr, &amp; Roan, 2014). The data used was collected from the 1993 and 2011 waves when participants were an average of 53 and 71 years old. Variables were created from self-report survey items from Ryff&rsquo;s Psychological Well-Being Scales (Ryff &amp; Keyes, 1995), the Big Five Inventory, version 54 (BFI-54) (John, 1990; John, Donahue, &amp; Kentle, 1991), self-report data on sexual behaviors, and demographic information. Two-way mixed effects ANOVA and hierarchical multiple regressions indicated that sexual frequency, sexual satisfaction, and personality all predicted change in overall psychological well-being. Health and gender did not moderate the relationship between sexual behaviors and psychological well-being, however the relationship between personality and psychological well-being was partially moderated by health and gender.</p><p>