In recent years, an increasing number of ultra-Orthodox Jews have left their insular communities, choosing instead to lead a secular life. This article illuminates their perceptions and experiences related to sexuality, sexual behavior, and sexual health. Based on thematic analysis of 37 in-depth, semi-structured interviews with ultra-Orthodox disaffiliates, we found that sexual experiences have played a decisive role in the disaffiliates' lives. First, some participants shared that experiencing sexual abuse during childhood led them to disaffiliate. Second, prior to disaffiliating, participants had very little knowledge about sex, which was an unspoken issue. This resulted in misunderstandings and miscommunication related to courtship and dating after disaffiliating. Moreover, the knowledge gap of secular social norms led to disaffiliates being sexually exploited, as well as to male disaffiliates behaving inappropriately and consequently suffering from social rejection and loneliness. While some participants celebrated their new sexual freedom, others were fearful and reluctant to have sex. We suggest that in transgressing social, cultural, and identity boundaries, disaffiliates experience "cleft habitus" and are situated in a prolonged liminal position that affects their sexual behavior, intimate relations, sexual health, and body image. During the liminal period, disaffiliates typically learn threshold concepts, which are often troublesome and threatening. There is a striking need to offer disaffiliates assistance and support throughout this difficult process. This analysis can shed light on other groups of religious disaffiliates and cultural immigrants.