Five Women spans approximately two years in the lives of five women doing their best to navigate life in New York. The plot, which is moved forward using both heartbreak and humor, begins in the East Harlem apartment of Lauren, a struggling artist in her early 20s. She is with her disapproving mother, Elaine, who has unexpectedly stopped by in an effort to talk her daughter out of pursuing her dream of becoming a successful artist. Lauren, however, remains resolute and refuses to follow a career path more in line with her mother’s wishes; a career more “respectable” and “worthwhile.” This is the beginning of what will gradually become a full-blown estrangement that, interestingly, not only makes Lauren feel like a bad daughter, but makes Elaine feel like a bad mother.

Fortunately for Lauren, her older sister, Marilyn—a high-powered New York attorney—is always there to lend a helping hand. Marilyn, unlike Lauren, is emotionally mature, undeniably successful, and financially secure. For nearly two years Marilyn serves as a source of emotional comfort and support. But then, Lauren finds out that Marilyn, at some point, began to secretly pay someone to pose as an admirer of Lauren’s art. And to make matters even worse, Marilyn financed that person’s purchases of several paintings by Lauren. This shocking news brings into question everything Lauren thought she knew about Marilyn. Lauren is ready to cut off Marilyn, until their dramatic and emotional confrontation about the matter, when Lauren finds out that Marilyn has been dealing with some life struggles of her own; struggles she has kept to herself.

Elaine, simultaneously, is also going through heartache and heartbreak, as she questions her handling of the ongoing conflict with Lauren. The situation is especially difficult for Elaine because it brings up old wounds involving her own mother. Details of Elaine’s background are revealed via monologues with her fiancé, Nigel Stuart Royston Porter Fox III, a British CEO, who has settled in upstate New York. Nigel is never seen, nor heard from. Instead, the audience is only able to watch Elaine speak to him through her monologues. As it turns out, Elaine is a truly tender-hearted woman, who for her entire life, has suffered and sacrificed a great deal for her daughters; more than they’ll ever know.

Meanwhile, a romantic sub-plot is going on between Grace (an Asian-American attorney at Marilyn’s law firm) and Chandra (Marilyn’s high-fashion supermodel roommate). Grace is a life-long lesbian and serial monogamist, who first meets Chandra at a wine-tasting party that Marilyn throws for all of the senior associates of her law firm. There is an instant attraction between the two women, who begin a relationship shortly after the party. Unfortunately, things don’t work out because Chandra has a substance abuse problem that is fueled by what she must endure on a daily basis in the modeling industry: sexism, misogyny, unreasonable dietary restrictions to stay “model-weight,” impossible standards of perfection/beauty, and even sexual harassment/molestation. Act I ends with the highly dramatic break up of Chandra and Grace.

All of these stories collide with each other and find resolution in Act II, when Grace suddenly and unexpectedly dies. Her death puts everything in perspective for the women, who are devastated. As Elaine explains to Lauren in the last scene, “Grace helped me finally understand what’s important in life, and also what’s not important.” By the end the play, the main themes that have emerged are faith, hope, and love: faith in those who are closest to us; hope in future possibilities; and love for each other that is unconditional.