Set in Philadelphia, The Watermelon Woman is the story of Cheryl (Cheryl Dunye), a twenty-something Black lesbian struggling to make a documentary about Fae Richards, a beautiful and elusive 1930s Black film actress popularly known as "The Watermelon Woman." While uncovering the meaning of Fae Richards' life, Cheryl experiences a total upheaval of her personal life. Her love affair with Diana (Guinevere Turner), a beautiful white woman, and her interactions with the gay and Black communities are subject to the comic yet biting criticism of her best friend Tamara (Valarie Walker.) Meanwhile, each answer Cheryl discovers about the Watermelon Woman evokes a flurry of new questions about herself and her future. At the film's conclusion, the Watermelon Woman is clearly a metaphor for Cheryl's search for identity, community, and love.

Soraya Nadia McDonald is the award-winning cultural critic for The Undefeated, ESPN’s premiere platform covering race, sports, and culture. She writes about film, television, and the arts. She is the 2020 winner of the George Jean Nathan prize for dramatic criticism, a 2020 finalist for the Pulitzer Prize in criticism, and the runner-up for the 2019 Vernon Jarrett Medal for outstanding reporting on Black life.