This chapter focuses on a selection of teen couples in the 1950s, who were “going steady” and experimented in intense and intimate sexual acts, including premarital intercourse. Going steady—a practice that was in the mainstream of postwar culture—was a pervasive site of sexual initiation, exploration, and exhilaration. Often, it was also the context for sexual coercion, unintended pregnancy, and punitive intervention. Steady relationships illustrate both framed and veiled widespread premarital heterosexual activity. The increase in sexual promiscuity fueled what was arguably the most important ideological development in postwar youth sexual culture: the “permissiveness with affection” sexual standard. This belief in the acceptability of heavy petting and even intercourse between members of a steady couple provided girls a compass for navigating the minefield of sexual contradictions.