The nature of intimacy and self-identity changed profoundly over the past century. The disruption between sex and procreation enabled the emergence of new forms of relationships and contributed towards the legitimacy of a sexuality focused on pleasure, as a mean of self-realization and an expression of intimacy. Despite the evidence that most individuals now approach close relations with expectations of mutual emotional support and romantic love, intimate relationships remain highly gendered, particularly in societies where traditional roles of men and women persist in the growing diversity of sexual relationships. To address this topic, an empirical research was conducted in the Greater Lisbon area using a mixed methods approach. First, a quantitative study, with 323 primary healthcare users, intended to explain how gender influences self-constructions of sexuality and intimacy. Then, a qualitative study, with a subsample of 10 heterosexual men and 15 heterosexual women, employed in-depth interviews to explore how individuals construct their etiquette of sexual behavior. Building upon Gagnon and Simon’s scripting theory and Giddens’ transformations of intimacy, along with feminist criticisms concerning male dominance in hetero-relationships, we have reached an explanatory typology that focuses on Portuguese specificity in terms of the subjective experience of sexuality and intimate relationships. Sexuality and intimacy are complex and multifaceted phenomena that are affected by sexual and non-sexual factors, both in and out of the bedroom. Key findings reveal a coexistence of highly gendered sexual scripts with increasingly more egalitarian sexual roles, namely among the youngest and the most educated generations in Portuguese society.