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How Stella Got Her Groove Back is a 1998 romance film, directed by Kevin Rodney Sullivan and an adaptation of Terry McMillan's bestselling novel by the same title. The original music score was composed by Michel Colombier.

The movie follows Stella (Angela Bassett), a divorced 40-year-old stockbroker who decided to forgo romance to focus on raising her son and advancing her career. She is persuaded by her best friend Delilah to take a well deserved, first-class vacation to Montego Bay, Jamaica. As she soaks in the beauty of the island, she encounters a strapping young islander, Winston Shakespeare (Taye Diggs, in his film debut), who is 20 years her junior. His pursuits for her turn into a hot and steamy romance that forces Stella to take personal inventory of her life and try to find a balance between her desire for love and companionship, and the responsibilities of mother and corporate executive.


Tropes associated with this work:

  • Amicable Exes: Stella and her ex don't seem to hate each other's guts, as the husband makes an appearance at a family function and is not hated. Her son also seems to be perfectly fine with his father and there was no mention of a custody battle or a messy divorce.
  • Author Avatar: Stella is one for Terry McMillan, as the book is inspired directly by something that personally happened to her.
  • Big Fancy House: Stella's home is absolutely beautiful. And huge.
  • Black Gal on White Guy Drama: Surprisingly averted with Stella's sister, who is married to a good-looking white man, yet there is no tension among her family members and he seems perfectly comfortable at family functions.
  • Control Freak: Winston accuses Stella of being one after they've been dating a while. He's not entirely wrong, as Stella does have to have everything a certain way, but she's not completely rigid and uncompromising.
  • Deadpan Snarker: Delilah, Stella's best friend. She's by far the funniest character in the film, but it's no wonder, as she's played by Whoopi Goldberg.
  • Definitely Just a Cold: How Delilah plays her illness. She doesn't tell Stella she's sick after she returns to New York. Stella only finds out when her surgery didn't go well and Delilah had Stella listed as next of kin.
  • Differing Priorities Breakup: Winston is still young enough not to have his career in order and all the pressure from Stella's family and friends pushes him to break up with her and go back to Jamaica to attend medical school.
  • Eating the Eye Candy: Stella can't help but check Winston out when they first meet, completely with amusing internal monologue thoughts in her narration.
  • Fanservice: The movie is quite fair in distributing fanservice for both men and women. Stella's utter beauty is on display both clothed and partially clothed and Winston is shirtless and later completely naked.
  • Feigning Healthiness: Delilah, during the trip to Jamaica. Once it's over, it looks like her illness starts to rapidly take over and she's hospitalized not too long afterward.
  • The Film of the Book: Based on Terry McMillan's bestselling novel.
  • Hopeless Suitor: A minor character Delilah and Stella meet in Jamaica who is supposedly an ex-athlete with money. He is overweight, much older than her, corny, and not the least bit self aware.
  • Informed Ability: Strangely enough, the film mentions Stella wanted to become a carpenter and make furniture, even noting she did it as a child and into her later years, but the film itself never shows her work on a single piece.
  • Kicked Upstairs: Subverted. Stella finds out after she returns from Jamaica that her company merged with another and her job was given to another executive without her knowledge. She finds out when she comes in to work and all her login information doesn't work, which leads her to confront her supervisor. However, months later, she gets called back in and the company realizes how many millions of dollars she made them, so they offer her twice her original salary and better perks to return. Ultimately, she turns them down due to her Character Development, realizing she'd rather pursue her passion than continue answering to The Man.
  • Likes Older Women: Winston pursues Stella with no regard to her age. Or maybe because of it.
  • Older Than They Look: Stella could easily pass for thirty until you hear her talk, as her sensibilities clearly show she's older than that.
  • May–December Romance: Stella is twice Winston's age.
  • Modest Orgasm: Done to show that the two of them make up after a big fight, though it isn't enough to keep Winston from breaking up with Stella and intending to go back to Jamaica to start medical school.
  • Parental Marriage Veto: Winston's mother is only a year older than Stella, and is not happy with the relationship.
  • Race for Your Love: In typical rom-com form, Winston is going to return to Jamaica to start medical school and breaks up with Stella. Stella starts to let him go, but has a breakdown and races to the airport, catching him before he makes it to the gate and accepting his proposal. He decides to stay.
  • Rejected Marriage Proposal: Subverted. Stella doesn't immediately say yes. After a week of no answer, Winston gets frustrated and assumes she's stalling because she doesn't want to say no, so he eventually decides to move back to Jamaica and start medical school.
  • Running Gag: The age gap is brought up ad nauseum. Winston himself even lampshades it at their third meeting in Jamaica, telling her to say it another three million times so he never has to hear it again. He truly doesn't care about the age gap and wants to pursue her regardless.
  • Sassy Black Woman: Mostly averted but for Delilah (played by Whoopi Goldberg, so no surprise) and Stella's younger sister (played by Regina King). Most of the other black women are like Stella, who is not stereotypical.
  • Sexy Discretion Shot: Interestingly, only for the first love scene. In the second one, Winston is shown completely naked in the shower and they're shown in bed together explicitly with both having a powerful Modest Orgasm.
  • Shower of Angst: Winston takes one after a fight with Stella. She joins him though and it becomes a Shower of Love.
  • Shoo Out the Clowns: The first half of the film is a light-hearted rom-com about Stella and Winston falling for each other during her trip, with Delilah as the titular clown adding in superb humorous lines. As soon as they leave, though, Delilah's illness rapidly begins to take over and she dies in the second half of the film. After that point, the humor is over and the rest of the film plays out as a drama instead.
  • Spoiled Sweet: Stella. It's made very clear she is loaded based on her Big Fancy House and the fact that she has $5,000 open on a credit card at Bergdorff's, but she's still a nice person and only has a sharp tongue when provoked.
  • Too Dumb to Live: A subversion. Winston ambushes Stella by taking her to meet his parents without her prior knowledge or consent. Naturally, it goes horribly wrong. Winston's mother—who is only one year older than Stella—corners Stella and rudely calls her desperate and tells her she should be ashamed of herself. Winston absolutely should have known better.
  • Twerp Sweating: A surprisingly inverted case with Winston and Stella's son. After Winston moves in with them, her son confronts him alone and solemnly asks if he'd ever hurt her. Winston takes the conversation completely seriously and even encourages the boy, telling him Stella will always be okay as long as her son is there for her.


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