Sexual experience is considered an important developmental milestone for emerging adults. Whereas some sexual experiences incur benefits, others are associated with negative mental health outcomes. This chapter first describes the cultural context in which emerging adults experience their sexuality, including sexualized media, sexual scripts, hookup culture, and technology, and the impact of these contextual forces on emerging adults’ psychological well-being. The mental health effects of sexual behaviors are also discussed as they relate to various relational contexts, including committed romantic relationships, casual “hookups,” and ongoing casual relationships (e.g., “friends with benefits”), with an emphasis on the disproportionate negative outcomes for women and the limited empirical research on the impact of these experiences on racial and sexual minority individuals. The chapter further discusses the mental health outcomes affecting emerging adults with sexual and gender minority identities. The chapter concludes with important directions for future work, including longitudinal studies and greater attention to intersectionality.