This study investigates weddings as moments of transition for women in three plays by American women playwrights in the late twentieth century. The study builds on the works of Gayle Austen and Judith E. Barlow on plays by American women through the application of the ideas of Stephanie Coontz, Jaclyn Geller, Chrys Ingraham, Jackie Stacey and Lynn Pearce. Jane Bowles's In the Summer House (1953) investigates the influence of the mother-daughter relationship on female identity formation and the resulting anxieties regarding marriage and maturation produced by the complexities of the mother-daughter bond. While exploring the bride's psychology, the play also probes the relationship between socio-economic conditions and marriage, showcasing how economic realities inform women's experiences of weddings. Henley's Impossible Marriage (1998) considers the tensions between societal conventions and personal desires, asserting the existence of true love while demonstrating the challenges society places on the individual's passions. Finally Ruhl's Eurydice (2006) showcases how multiple types of love affect women by moving Eurydice from the myth's margins into the play's center. In imagining loves intertwinement with loss, the play disproves the belief that romantic love ensures eternal happiness and makes up for past tragedies.