With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

Romantic comedies are about wish fulfillment, so that makes them a fascinating case study in which wishes Hollywood is interested in fulfilling. 1998’s How Stella Got Her Groove Back wasn’t the first rom-com with a predominantly black cast, but it’s notable for being a high-profile one that centers on a 40-year-old black woman figuring out what she wants from her romantic life. Though it’s probably better remembered for its goofy name than its actual storytelling, How Stella Got Her Groove Back has more to say than its steamy, silly title might suggest. It’s an intriguing rom-com about the line between fantasy and reality, even if it ultimately stumbles when it has to finally pick a side.

Made in the middle of the 1990s rom-com boom, How Stella Got Her Groove Back was also part of a wave of mainstream black cinema that emerged during the decade. It specifically followed on the heels of the Forest Whitaker-directed 1995 romantic drama Waiting To Exhale, an adaptation of Terry McMillan’s best-selling novel about four friends navigating the trials and tribulations of love and heartbreak. Starring Whitney Houston, Angela Bassett, Lela Rochon, and Loretta Devine, that film’s unexpected financial success proved there was an audience hungry for interpersonal dramas about upper middle class black women. (It also lives on in a big way through the frequently used GIF of Angela Bassett walking away from a burning car.) Hoping to recapture some of the same magic, McMillan’s next novel was greenlit for a film adaptation as well. As she had with Waiting To Exhale, McMillan worked with prolific Hollywood screenwriter Ron Bass to adapt her own novel for the screen. This time around, however, McMillan traded in the more serious, contemplative tone of Waiting To Exhale for something a little steamier.

In the midst of a career high and just a few years out from her Oscar nomination for What’s Love Got To Do With It, Angela Bassett stars as the titular Stella Payne, a successful 40-year-old stockbroker who’s too focused on her career and her son Quincy (Michael J. Pagan, adorable) to have much interest in dating. But during an uncharacteristically spontaneous Jamaican vacation with her best friend Delilah (Whoopi Goldberg), Stella soon finds herself being aggressively wooed by 20-year-old Winston Shakespeare (Taye Diggs), a recent college grad who isn’t sure he wants to pursue the med school path his parents have laid out for him. Though she’s self-conscious about the fact that she’s “old enough to be his mother,” Stella eventually gives into vacation pleasures and “gets her groove back” with Winston. Once the vacation is up, however, Stella and Winston can’t quite seem to quit each other. They’re soon living together back in the States and trying to figure out if the differences between them are too deep to forge a real relationship.

A much-hyped element around the film’s release was the fact that How Stella Got Her Groove Back is loosely based on Terry McMillan’s real-life experience. She was a 40-something divorced mom who fell in love with a 20-year-old Jamaican local while on vacation and wound up marrying him. In retrospect, however, McMillan’s real-life fairy tale is complicated by the fact that her marriage ended in a fairly acrimonious divorce in 2005, at which point McMillan publicly questioned whether the relationship had ever been real. But even though McMillan and the filmmakers didn’t know what was to come in her real life, How Stella Got Her Groove Back is explicitly about the tension between reality and fantasy. The first half of the film is a fairly silly romp with lots of great Whoopi Goldberg humor and plenty of female gaze-y shots of Diggs’ biceps. But the second half takes a turn for the melodramatic, marked by the moment Delilah suddenly comes down with a debilitating illness. While some rom-coms create heightened, artificial obstacles to drive their romantic leads apart, the second half of How Stella Got Her Groove Back seriously grapples with the 20-year age difference between Stella and Winston.

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The film’s two tones don’t always work in harmony. The first half flies by while the final 30 minutes seem to drag on for hours. Conceptually, however, there’s something admirable about a rom-com that wants to acknowledge that it actually takes a lot of work to maintain a romantic relationship and to balance dating with things like career, parenting, family, and friendship. As with the best ’90s rom-coms, there’s welcome texture to the film’s world, which is something the glossier rom-coms of the following decade would lose. Stella is full of great little moments that don’t serve a particular plot function, but which make the world of the film feel like it exists beyond what we see on screen. Stella’s big dream is to design and construct furniture, which is delightfully random. There’s a sweet scene where Winston meets Stella’s family and gets along well with her ex-husband. In addition to her romance with Winston, Stella has warm, realistic relationships with Quincy and Delilah, as well as with her sisters Angela (Suzzanne Douglas) and Vanessa (a hilarious Regina King). Throughout it all, Bassett ensures Stella always has a real sense of dignity, even as she calls herself out for acting like a love-struck college student.

In his directorial debut, Kevin Rodney Sullivan makes the smart choice to celebrate Stella’s grace, beauty, and sexuality without ever objectifying her. In fact, Sullivan often films Bassett—and her incredible arms—like she’s a full-on superhero. Instead, the film saves its leering camera shots for the absurdly named Winston Shakespeare. Much of the fun of How Stella Got Her Groove Back is watching the film subvert norms about how men and women are portrayed in romances—including a shower sex scene where Stella remains clothed while Winston’s body is on display. (The film’s gauzy sex scenes are perhaps the most ’90s thing about it.) Following his breakout role in the original Broadway cast of Rent, How Stella Got Her Groove Back gave Taye Diggs a fairly auspicious start to his film career. He certainly fits the Adonis-like quality the film is looking to capture in Winston, and Diggs would pivot this role into a successful career as the leading man in a whole host of other black rom-coms. But Stella doesn’t take advantage of Diggs’ natural charisma as well as some of his later roles would (it doesn’t help that he never quite seems comfortable with his Jamaican accent). In fact, Winston often comes across as weirdly serious and solemn despite the fact that we’re constantly told how immature and fun loving he is.

Beyond the age gap itself, the bigger issue in Winston and Stella’s relationship is that Winston is just really young. As Stella tells Delilah, “He hasn’t even had his heart broken yet.” The fact that Diggs was about 26 when he shot the film somewhat elides the reality that Winston is supposed to be just two years into official adulthood. (Bizarrely, Ron Bass’ previous rom-com, My Best Friend’s Wedding, also featured a 20-year-old character eager to settle down with someone older than her.) But the film also leans into Winston’s immaturity by having Stella complain that he eats Cocoa Puffs in bed and spends his days playing video games and watching Disney movies. The film really explores the awkwardness of their dynamic when Stella meets Winston’s parents and discovers that his mom is just a year older than her. At the same time, it’s worth acknowledging that in a gender-flipped version of this story, the man would almost certainly be in his 50s or even 60s because 40-something men being paired with 20-something women is kind of the norm in Hollywood casting.

For its final act, How Stella Got Her Groove Back has to decide which element it wants to emphasize—the romance or the realism. In the end, Stella feints at pragmatism before ultimately going for fantasy. And that might be its fatal flaw. The film gives Stella and Winston a really lovely breakup scene in which he maturely acknowledges that even though they love each other, the differences between them are just too insurmountable. Like My Best Friend’s Wedding, the film easily could’ve ended on a bittersweet but hopeful note. Instead, How Stella Got Her Groove Back goes for the pure fantasy route as Stella changes her mind and races to the airport to accept Winston’s earlier marriage proposal.

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As Roger Ebert noted, it’s only a happy ending if you’re willing to forget the strong argument the film just made for why Stella and Winston shouldn’t be together. Yet considering the dearth of rom-coms centered on black women—let alone ones in their 40s—I’m sympathetic to the fact that How Stella Got Her Groove Back clearly wanted to offer a wish-fulfillment romance with a happy ending. Ultimately, the film probably works better as a character study of Stella than it does as a romance. But there are definitely worse ways to spend two hours than watching Angela Bassett embrace her groove.

Next time: The Devil Wears Prada and rom-coms that aren’t really rom-coms.