This chapter examines the immediate and long-term consequences of first sexual involvement in dating couples. Drawing on the “passion turning point” construct articulated by Baxter and Bullis (1986), research is reviewed that suggests the events or elements within the passion turning point (first kiss, first sex, “I love you,” and the whirlwind phenomenon) are not only conceptually related, but also temporally related. More specifically, an argument is advanced that when expressions of love occur prior to first sexual involvement in dating relationships, the event is more likely to have positive consequences for the relationship both immediately and over time for relationships that continue to develop. In addition, research is reviewed to suggest that attachment orientations may contribute to how variations in the sequencing of the passion turning point are interpreted both immediately after first sex and over time. A survey study of college students who have experienced first sex in a current or recent past relationship is presented as a preliminary test of the arguments derived for related literature.