Despite professional success, the 1990’s was a difficult decade for Terry McMillan. Her mother, Madeline Tillman, died in September of 1993, and the following September her best friend, Doris Jean Austin, died. Emotionally drained, McMillan traveled to Jamaica in June, 1995, with Deborah Schindler, the producer of the film version of McMillan’s novel Waiting to Exhale (1992). In Jamaica, McMillan had met Jonathan Plummer, a twenty-four-year-old resort employee. Though McMillan had been concerned with the difference in their ages—she was nineteen years older than Plummer—the couple still fell in love.

Inspired by her experience in Jamaica with Plummer, McMillan returned home and spent the first three weeks of September writing the first draft of How Stella Got Her Groove Back. Her editor, Carole DeSanti, said that McMillan had written about her experience in Jamaica in several genres (that is, as a poem, a short story, and a novella) before the work evolved into a novel. McMillan’s ability to work had been surprising because prior to her vacation, she had been suffering writer’s block, unable to complete the manuscript for the novel A Day Late and a Dollar Short, which was published in 2001. Before December, 1993, McMillan had invited her muse—Plummer—to join her in California. Known for creating works thinly veiled as fiction, McMillan admits the novel comes close to mirroring her experiences.

The novel depicts the details of a romantic relationship between Stella, a forty-two-year-old woman, and Winston, a twenty-year-old man. Concerned by the age difference between them, Stella worries about what people will think of her until she remembers that men are often admired when they date or marry women half their age. She resents this double standard and decides she is brave enough to live her life in a way that pleases herself, not others. This type of empowerment is often found in McMillan’s novels, in which her protagonists are generally successful, professional, and courageous women who are also autonomous and strong.

Friendship and romance also are important themes in McMillan’s work. The skillful way in which she uses vernacular, realism, and humor is reminiscent of work by Ann Lane Petry and Zora Neale Hurston. However, McMillan’s work has usually been labeled popular fiction, often to her chagrin.

Some critics had been unimpressed with the style and structure of How Stella Got Her Groove Back, citing its use of the stream-of-consciousness technique, its minimal punctuation, and its excessive profanity. Other critics believed that her focus on romance pushed her farther away from her goal of being a “literary” writer. Despite the criticism, McMillan’s readers helped make the novel a best seller.

McMillan has been credited with showing the publishing industry that readers will support African American writers. In 1996, when the novel was in production, no other African American writer had been promised a first printing as large as the 800,000 copies that had been planned for How Stella Got Her Groove Back. Two years later, a film version was released, and it, too, was a success.