Welcome to Love Like This?, a romance column where we, Kathleen Newman-Bremang and Ineye Komonibo, revisit some of the most romantic — or not, in hindsight  — scenes in Black film and TV history.

Stella got her groove back exactly 24 years ago this week — allegedly. In August 1998 when How Stella Got Her Groove Back premiered, Taye Diggs was a relatively-unknown Broadway actor (having starred in a little musical called Rent), and Angela Bassett was, well, Angela Bassett. The film, an adaptation of Terry McMillan’s bestselling romance novel (and real life experience with a not so happy ending), was billed as a fun, romantic romp about Stella (Bassett), a 40-year-old uptight, high-powered investment analyst in a rut who meets Winston (Diggs), a 20-year-old handsome islander in Jamaica during a vacation with her best friend, Delilah (Whoopi Goldberg). The title (and our adolescent memories) implies that the relationship is just a fling, a detour en route to Stella finding her groove again. But Stella and Winston fall in love, and a good chunk of the film explores what happens when age becomes more than just a number. Can their love withstand judgmental glances, raising her 11-year-old son, and clashing career goals? 

The movie was met with mixed reviews. Roger Ebert gave it two and a half stars, writing, “Stella may indeed have her groove back, but at a considerable price, and maybe not for long. If a romantic couple feels wrong to the audience, no plot gymnastics can convince us.” While The Hollywood Reporter called Bassett “sensational” and her performance “stewing, simmering, smoldering” opposite Diggs’ “appropriately alluring and steady” film debut. These duelling reviews get to the heart of what’s so great (and what’s not) about How Stella Got Her Groove Back: Diggs and Bassett are indeed sensational, simmering and smoldering together, but the story — and the status of Stella’s groove — leave something to be desired… and not just more shirtless Taye Diggs in his prime. 

How Stella Got Her Groove Back is the perfect August rewatch because not only does it make you want to head to a beach immediately with your best friend, it’s also the shot of nostalgia (look for cameos by Regina King and James Pickens Jr.) we need to help us forget that summer is coming to an end. Over two decades later, it’s time to ask if we would really want a love like Stella and Winston have? And did Stella leave her groove back in 1998? 

The Scene: Months after returning from Jamaica to the U.S. together and trying their hand at a serious relationship, things between Stella and Winston have become very complicated. Even though they love each other and want to be a real couple, life is getting in the way, and they’re finding that their many differences might unfortunately be too challenging to overcome. Winston is feeling the pressure of being the younger, less accomplished partner to an older woman who already has her life fully underway, and Stella can’t help but be tense by the prospect of other women eyeing her partner. 

In what should be a brutal breakup — it plays out rather calmly — Winston informs Stella that he’s heading back to Jamaica to pursue his medical degree. She only barely protests, and after one final night of lovemaking, they silently agree to go their separate ways. Winston tells Stella that he loves her, gives her a kiss, and heads straight to the airport.

It’s not long before Stella, despite her typically logical thinking and pragmatic approach to life, realizes that she loves Winston far too much to just give him up. She rushes to the airport in hopes that she’s not too late, and as fate would have it, Winston is also stalling before boarding his flight. (He really loves this woman.) Upon seeing each other at the bustling airport terminal, Stella finally tells Winston what he wants to hear: “Yes. Yes. Yes.” It’s a yes to his formerly brushed-over marriage proposal but also a yes to building a life together, no matter how hard things get. The couple happily embraces each other, sealing their promise with a kiss.

Does The Grand Gesture Hold Up? 

Ineye Komonibo: In terms of grand gestures as a genre, I feel like it was pretty lacklustre. For the situation, the context, and for them as a couple, I think it holds up. 

Kathleen Newman-Bremang: I agree that it works for their relationship. It’s lacklustre because all she needed to do was show up for him to forgive her and want to stay. It was that simple. She didn’t have to put in much effort. But I was also thinking, why are you making a grand gesture for a 20-year-old? Why are you, a grown ass woman, going out of your way to rush to the airport, to get there before him, and to declare your love to get him to stay with you when the man is 20-years-old and should be at home with his mama? Make it make sense! Plus, a grand gesture works in a romance movie when there is an epic speech that goes along with it. And she didn’t say one.

IK: You know I’m typically against women doing grand gestures for men, but if you’re gonna do it, sister, you need to do it. I understand that Winston is 20, and he’s like a puppy, so he just wanted her to show up, and that was fine. I feel like it was kind of dry, though! Just showing up at the airport is not enough, Stella. You don’t have anything romantic to say? You don’t have a present? Show up with some flowers or a beef patty or something! Anything! It was too easy. In terms of romance and grand gestures, it was dry, but it does hold up for their relationship. So I’ll allow it…I guess.

KNB: I’m not on board for this relationship in general, which hurts my soul because I love Angela Bassett and Taye Diggs as actors so much. But I’m not on board for Stella going out of her way for anyone, especially this boy. That’s not who she is. 

Could It Be Me? 

KNB: Okay, I know I said I didn’t like it, but I could see myself doing this [laughs].  By now, we know I’m a bird. If I was really into someone, I would show up at the airport and tell them to stay. I still don’t like it for her and for him, but I could see myself making this specific grand gesture because it’s so simple. She just says “yes,” — presumably to Winston’s proposal — and that’s it. I’m not gonna show up with a f-cking marching band, but I could see myself just being like, I’m here, take it or leave it. 

IK: But you would have something to say. I would have liked to understand why exactly Stella was there. What changed her mind? What is it about Winston that made her do this thing that was so out of character for her?

As far as whether or not it could be me, I don’t think I’m showing up to the airport, man. I’m a really proud person, so I don’t know that I could turn someone’s proposal down or let them leave and then go and beg for them to come back. I mean, if I really, really love the person, I might have to admit that I messed up or that I made a mistake, but I would be so anxious about showing up to the airport just for him to tell me it’s too late. I would be embarrassed. So yeah, instead, I’d probably instead just let him leave and maybe go to Jamaica a little later or pray that he sends me a Whatsapp message or something. I’m not judging Stella for doing it, but I don’t know if it could have been me.  

Rate The Kiss

KNB: The kissing in this movie is god tier. 10/10 no notes. The love scenes are beautiful, seamless, and so sexy. Even the final kiss was giving pure LUST. I would watch 100 more hours of Taye Diggs and Angela Bassett making out. These are two of the finest, most attractive human beings to ever grace Hollywood. More, please. 

IK: Taye Diggs has never had a single bad on-camera kiss in his entire career, and How Stella Got Her Groove Back is no exception. They were K I S S I N G, I tell you! The chemistry between these two is actually overwhelming. Respectfully, I want to be in the room!

Rate Taye Diggs’ Accent

IK: I have a question for you as a Jamaican person. I feel like Jamaica doesn’t show up unless a white person is going on vacation, so we rarely see the accent done well. Was Taye Diggs’ accent giving? 

KNB: Oh, f-ck no. Listen, I cannot speak patois well or do a good Jamaican accent; this is why I never do an impression of my family because they make fun of me for it. I’m just not good at accents and never have been. My accent sounds like Taye Diggs. He was bad. This was his first ever movie role, so we’re going to give him some grace, but it absolutely was not giving what it should have given. I’m also gonna give him some grace because he’s so damn charming and HOT in this role. Hollywood gets no grace though. Hire an actual Caribbean person or someone you can do the accent well, I beg. 

IK: He was really good. I mean, the accent was trash, but he, as an actor, was really good! 

How Do We Really Feel About The Age Difference? 

IK: 20 years, man. No! It’s not even just because he’s younger than her; Winston doesn’t have anything going on in his life except being fine. It’s giving vacation boo. I hate that Stella took Winston home — you’re supposed to leave him where he is, ma’am! He’s so young, and he doesn’t have anything going for him right now. Throughout the movie, Stella has to make him feel better that he doesn’t have anything else going on. And on the opposite end, Stella is kind of getting in the way of his life. Winston has a whole life ahead of him, but she’s sort of stifling him as her house husband. I don’t like that.

KNB: Yeah. I agree. My hot take on age differences in relationships is that they can only work if you are at the same point in your life. A lot of people reach different stages of their life at different times. A 30-year-old and a 50-year-old could be at the exact same point in their life as far as career, being financially independent, even having a kid or two. So that age gap could work. If you’re at the exact same stage in your life, I’m all for it. The age gap could even be smaller but if you are at two completely different stages of your life, it’s not going to work. If you’re 25 and 30 and you’re at different stages in your life, that shit doesn’t work. That’s why I cannot get down with this age difference because he is a 20-year-old who has barely started his life. And he even says it in the movie. He’s like, “you have a mortgage, you have a kid, you have this whole life. And I have nothing.” He literally says the word “nothing.” So even if the age didn’t matter, the fact that he said that out loud means it’s in his head. And he is never gonna get over that. 

Also, the fact that his mom is only one year older than Stella, absolutely not. It’s getting weird. He’s clearly got some mommy issues. As soon as I met his mom and found out that she’s only a year older than me, I would think oh, homeboy’s working through some mommy issues. This is about her, not me. Listen, I’m all about Stella getting her groove back. Yes, mama, get that good dick. But settling down and marrying this baby boy? It’s a no for me. 

IK: That’s all it should have been, though. What should have happened in this movie is that Stella should have been with Winston just to jumpstart her serious dating pursuit.

Stella got her groove back by getting into a serious relationship with a youth? That’s not it! That’s not what’s supposed to happen. You’re supposed to realise, oh I’m a bad one. I can get somebody equally as bad. I can start being out there on the streets again. When you get your groove back, you don’t go back inside the house with a young person who is also not ready to be off the streets. 

They should have pulled up the All-State man (Dennis Haysbert) or somebody older, somebody who’s also divorced or who has one kid, somebody grown. That’s what it should have been, as opposed to her chasing down a teenager — a guy who’s literally a year removed from his teens — to live with her and not pay rent. Winston really won.

Would You Want A Love Like This?

KNB: I’m all about a man doting on you and thinking you’re the greatest person in the world because that’s how my relationship works. I like how much Winston just loves Stella and supports her. She said she liked to make furniture and he’s like, “yes, absolutely. You should do that.” He fixed up that room for her to build her furniture. He’s all about supporting her dreams and is just obsessed with her as a human being and thinks she’s beautiful and perfect. No matter their differences, I like that for them and that’s the only love I would want. 

IK: Okay, but he literally has to do that. He has no option but to be Stella’s cheerleader. He doesn’t have anything else to do! Imagine if he was being super macho. Like, huh? You need to be my number one fan, bro. I’m taking care of your life! You should be supporting me in everything! I hear what you’re saying, and I do think that’s really cute, but it’s a given. He knows what he’s gotten himself into, so he has to act accordingly, period.

KNB: You’re right. It’s the bare minimum. But I did like that they had a lot of fun together. Stella was laughing a lot more with Winston. She’s smiling when she’s with him. Based on the first scene and seeing her at work, she’s not somebody who smiles a lot or who usually takes time for herself at all. So I like that kind of love. I think that we should all strive for somebody who makes you really f-cking happy and who lets you rest. Your relationship should be a point of rest and happiness and a reprieve from the rest of the world. It should be your safe space, and I do think that she had that with him, but I don’t know if he had it with her. He has no worries because he’s a 20-year-old, so it’s not like he had the same with her. They were both just in mad lust. And I get that, but you don’t build a life on some good D. It’s like when Jennifer Lopez was dating that dancer, Casper Smart. I hate that I remember his name. It was like, sure, f-ck the dancer on the low, but don’t bring him to red carpets. Don’t give him a job. 

IK: That’s why I feel like their “love” should have just been for a season. This is a phase of lighthearted energy and flirting and pure vibes. They click well because he inspires something youthful in her, and seeing her work hard makes him think, Oh I want to work hard, too. But their lifestyles don’t match up. When things aren’t fun anymore, when you have to buckle down and really work at this life thing together, they’re not bringing the same thing to the table. So at some point, it’s not enough to just be having fun. Stella needs a partner that she can rely on. This relationship should not have been that deep. 

I’m not even 40, but if I went to Jamaica, and a fine young ting approached me like, let’s have a fling for three months, I’m down. I love it! I love having fun, but I’m not gonna bring this man home in my suitcase with me. I have a real life, so I need a real situation. Something that is stable and somebody who can take care of me in ways that are just more than having fun together. Long term. I wouldn’t want a “love” like what Stella and Winston have. For a summer fling, though? I would’ve loved it. That’s so cute. 

Is This Couple Still Together? 

KNB: Absolutely not. There’s no chance. We also know how it turned out in real life for Terry McMillan (seriously, it’s a WILD story). But in the fictional world, Winston definitely goes to Stanford, meets someone his own age,  and they break up. Or she meets someone her own age and they break up. The exact same issues — even if no one else is involved — would keep popping up. There is no world in which these two last. First of all, this couple shouldn’t even have gotten together at the end of this movie, let alone are they still together now? Absolutely not. I rebuke it.

IK: No, they’re not still together. They might try to tough it out, but they’re not gonna make it down that aisle. They might even have a lavish engagement party (that Stella pays for), but they’re not getting married. He’s gonna keep living in the house, and when he gets into medical school, the long distance aspect of it is going to destroy them. Stella is going to be suspicious, and Winston will be like, Wait, why are you checking me? You’re not my MOM. And that first “you’re not my mom” will send the relationship in an entirely different direction. In fact, I actually hope that to spare themselves the heartbreak, they break up the very next day they get home from the airport. 

KNB: They didn’t even make it home from the airport. I think it’s one of the first times where I actually really enjoyed the movie and I really enjoyed the performances but I was not rooting for this couple at all.

IK: I was really waiting for another person to show up. I thought there was going to be a scene where Stella goes back to Jamaica with her actual man and sees Winston with somebody else, and they lock eyes and smile wistfully before going back to their respective partners. 

KNB: That would have been the perfect ending! Because did Stella actually get her groove back? She just got herself in another relationship with another man who’s going to force her to have another kid. 

IK: She’s not having that kid. If they get married, they’re gonna get divorced. And now Stella is gonna have to go back to Jamaica and find somebody else.

KNB: Are we casting the sequel right now? Who is an age-appropriate fine-ass Black man to play opposite Angela Bassett? And Taye Diggs is having a moment as a TikTok star right now, so I could see him playing a bumbling side character. Winston is still eating his Cocopuffs and playing video games at 40. Still fine, still a wasteman.

IK: Yes, he’s her chaotic ex. You know who would be the love interest? Delroy Lindo. I feel like the chemistry would be there. He needs to be spicy — we need someone who’s gonna butt heads with Stella! They’re gonna be at the Sandals Resort buffet reaching for the jerk chicken at the same time or something. A real meet-cute.

KNB: [laughs] I love this so much. This is a sequel I would be on board for. Let’s get our pitch ready. Studios, we’re coming! 

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