Cheryl, a twentysomething black lesbian, is struggling to make a documentary about a beautiful and elusive 1930s film actress, popularly known as the "Watermelon Woman." As Cheryl uncovers the meanings of the Watermelon Woman's life, she experiences a total upheaval in her personal life. She falls in love with a white woman, and banters about race and desire with her best friend Tamara. At the film's close, the Watermelon Woman is clearly a metaphor for Cheryl's search for identity, community and love.