This encapsulates my problem with this movie — the romance is supposed to help Stella (Bassett) get her “groove back,” but I think the premise is a little flawed from the get-go. She seems to have a different kind of groove from the beginning: she’s got a good job, great family relationships, and a cute kid. Yes, her love interest does seem to help her rediscover her passions, but I just don’t know if he was necessary for that to occur. The film is saying that Stella was too focused on a career to see what was missing in her life, but I’m not sure that by the end of the movie, she’s found what she was missing.

 

Stella is almost immediately introduced to the audience at work, where she’s a stock broker/account executive. Our first scene of her at work firmly positions her in the boss businesswoman category: she’s in a power suit, she rocks a headset, and she works on her day off. Initially, she seems great at her job, which her boss echos — he seems to need her to even be able to do his job. She does more math in these opening scenes than perhaps every female lead in any romcom I’ve watched up until this point. There is something satisfying in seeing a 40-year-old woman of color so in charge in a field that is very white and very male.

 

Yet, even with her seeming career success, the film is working hard to convince us that she’s missing something in her life. At the spa, her sisters try to set her up for what seems like the millionth time. She’s forced to relax because she “stresses enough at work.” This scene is a classic way of establishing Stella as the dedicated career woman who has put her life on hold for her job. Is Stella for sure putting career success before her love life? Yes, but she seems not to feel like she’s missing out on something.

 

I know this is a romcom, but Stella actually seems fine on her own. I’m not all that into the fact that this film, and just like society at large, assumes that single women definitely don’t want to be single, even if they say otherwise. Stella tells her girls she doesn’t need guidance from a man, and I respect the hell out of that. But, I can’t decide if this film wants us to believe Stella, that she really is happy how she is, and that is somehow how she’s emotionally ready to be in a relationship by the end? Or, does it want us to think Stella is pretending to be happy with being single? I’m leaning toward the latter, especially because of the way the film gets her down to Jamaica.

 

After seeing a very seductive TV ad for Jamaica, Stella makes an impulse decision to visit the island for a tropical vacation. But, she quickly talks herself out of it: she’s got “too much on her plate” AKA work. She’s got a deadline coming up with some shareholder reps. But, she’s pretty quickly convinced thanks, in part, to her best friend, played by Whoopi Goldberg. Whoopi is spot on for telling Stella that they should just go, she definitely has enough money to take this trip. Sidenote: Whoopi’s character seems to work in fashion in New York, which I find hilarious. Even in a romcom that does a lot to defy convention with both its heroine’s career and the setting, the movie can’t resist the classic “works in fashion in NY.” Ambiguous vacation policy at Stella’s job aside, she and Whoopi travel to Jamaica.

 

In Jamaica, Stella meets the much-younger Jamaican Winston Shakespeare, which is 100 percent his real name. He is 20 years old, and she’s 40, so she initially refuses his advances. But, because he’s played by Taye Diggs and is so cute in his swim trunks, she gives in, and the two get it on in various tropical bedrooms. She feels like it’s just a fling; they’re at such different places in their lives. Winston has just finished his degree in biology and is in search of a summer job, exploring the idea of becoming a chef.

 

This kind of leisurely exploration of careers is, the movie implies, a privilege for the young — Stella is a single mom and a grown adult who can’t afford to just do what she wants to do. As we learn with some pretty odd pillowtalk, apparently Stella’s true passion is to make and design furniture — we later find out she has a full-on studio in her garage, unused — which is very cool but also a little weird. Despite furniture being her passion, she now makes a lot of money in the “money markets,” living up to the expectation her parents set for her. Besides establishing the differences between them as Stella and Winston begin their romance, this first trip to Jamaica also gives the film a chance to gratuitously lean into the female gaze, giving the audience many a shot of Taye Diggs’s biceps. I’m not mad about it.

 

After a passionate time in Jamaica with Taye Diggs and his biceps, Stella must go back home and face reality — or so we think. He’s young and from another country, so the possibility their relationship is just going to be a fling is very high. On a break from the steamy island romance, the film decides to stir up some trouble in Stella’s highly structured life, and as she returns to her job, she finds out she’s been let go due to some complicated company merger the film smartly decides we don’t need explained in detail. I’m here for romance, not for math. I’m righteously angry for Stella, and she’s understandably upset, but when telling her son about it, she’s pretty chill about the “not having a job anymore” thing. Is this just evidence of her being a good parent and hiding hardship from her child, or is this movie not really interested in Stella grieving a job that, even though she was good at it, was never her passion? I think both.

 

Although losing her job magnifies the stress in Stella’s life, it seems her eternal vibe is that she “has a lot on her plate.” She seems to be trying to find a new job while simultaneously suing her former employer, taking care of Quincy, and coming to terms with feelings she still has for Winston. All of this combined is why this romance between Stella and Winston doesn’t really work in the long term for me. Winston as a hot vacation hookup for Stella is great, but as a life partner, he doesn’t really do anything to take things off her plate.

 

Time and time again, How Stella Got Her Groove Back provides us with an abundance of reasons why Stella and Winston are incompatible. She decides to work for herself and all he seems to do is just sit around her beautiful house playing video games with Quincy. They get into a huge argument over picking up the check — he has no income and pays in cash after storming out. They are just at incredibly different places in their life. Will he ever go to med school? They seem to avoid talking about the future. He likes junk food and cartoons, apparently.

 

Yet, there are moments where Winston’s potential for maturity seems to shine through. He  fixes up her garage so she can work on furniture again and it’s sweet that he’s encouraging her to follow her passions, if impractical. This impractically rubs off on Stella; when her old job wants her back and is willing to offer $275,000 to start plus incentives, she turns it down, which is a little crazy. Winston’s response is that this is great, it’s a chance to start working on her furniture again, but in a practical sense, Stella has just turned down a huge career opportunity with no back up plan. Would the old Stella have done that?

 

It’s perhaps a testament to just how different the film has made these two seem that when Winston proposes to her my first thought was WHY. She does seem to love him, yes, but she belittles him, and he has very little maturity. Their relationship seems to be all sensual and very little substance. Besides their age difference, what do they talk about? She says no to his proposal, which is probably a smart decision. When they break up, he says the thing I’ve been wanting to scream at her the entire movie: “a real man would be making things a bit easier for you.” Yes, he would, wouldn’t he, Winston. Continuing his last minute stroke of maturity, he also tells her: “You have a child and a mortgage and a career and I have nothing. And I’m not satisfied with that.” They break up and at this point the film is either heading toward the most mature breakup maybe ever or the it’s going to let the plot devolve into the least believable chase to the airport ever. I’ll let you guess which one.

 

Because this is romcom, she chases him to the airport (beating him actually, which is some kind of metaphor) and accepts his proposal, asking him to stay with her for med school. I’m torn over the end of this. I initially was angry at how unbelievable the two of them together at the end of this film actually is. All the problems that caused the breakup have not been solved. Yet, I think the desire for believability is not what this film was trying to give me. This movie can be thought of as a kind of wish fulfillment (especially because it’s based on a true story of the book author’s life), so who am I to begrudge these two happiness?

 

This film is asking me to put aside my doubts and trust that Winston and Stella will be happy together, which mirrors what Stella has to do at the end of the movie. Am I asking too much of a romcom for a believable ending or are films like this not in the business of reality? I have to trust Stella will find a job she loves with the man she loves, even if I can’t see it happening. Ultimately, I think this film accidentally sets up Stella as having a happy and fulfilling life without Winston, and I’m a little disappointed when these two end up together — is this Stella actually losing her groove?