It’s Super Bowl weekend, and I’m standing inside a 200,000 sqft warehouse on a waterfront pier in San Francisco, packed wall-to-wall with people, including more than a few of the sports and entertainment industry’s most recognisable faces. Russell Wilson and Ciara glide in, hand in hand, through the dense VIP section. Somewhere in the crush, Cardi B, Jon Hamm, and Ty Dolla$ign drift between clusters of guests. Big-name athletes fill nearly every corner of the room. The game is still two days away, and on this particular Friday night, Olivia Dean is the headliner everyone has come to see. “This is the first gig I’ve done since winning a Grammy,” Dean says, beaming, from the stage.
In the five days since she took home the Grammy Award for Best New Artist, Dean hasn’t had time to come up for air. She’s gone straight from music’s biggest weekend in Los Angeles to football’s biggest in the Bay. This performance, at a Super Bowl kickoff party hosted by Uber, is her final obligation before flying back home to London for a much-needed break. But you wouldn’t know that by watching her onstage, radiating bright as a beacon.
A few hours before her performance, I meet with the 27-year-old singer in her suite at The St. Regis to process this triumphant moment in her career in real time. She greets me warmly with a big smile and a welcoming hug, dressed casually in baggy Levi’s, black-and-white polka dot Manolo Blahnik pumps, and a tight black T-shirt. As we settle into the sofa, it quickly becomes clear that Dean romanticises life the way she makes music, turning ordinary moments into ones that feel worth lingering in. When she finds out it’s my birthday, she insists on gifting me a bottle of Veuve Clicquot champagne. “Why are you here working?!” she exclaims. “Uh, do you know who you are?! You just won a Grammy!” I shoot back. She shakes her head, hands pressed to her face, laughing softly, still not quite ready to believe it. “My heart is extremely full in a way that is kind of hard to even describe,” she says. “I did not think that was going to happen. I can’t lie to you. I’ve never won an award for music before.”
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Winning one of the most sought-after Grammys as your first-ever award is pretty iconic, but it’s a fitting result of the momentum Dean’s been riding since the release of The Art of Loving in September. While it wasn’t her debut—she had already released multiple EPs and a 2023 studio album, Messy—it was her first time breaking through on both sides of the Atlantic. The album quickly reached platinum status in the UK and gold in the US, and songs like “So Easy (To Fall in Love),” “Man I Need,” and “A Couple of Minutes” went viral across TikTok and Instagram. Add in standout live performances, a Burberry campaign, and critical raves, and Dean has become inescapable.
She tucks one leg beneath her on the couch and lifts the other into an easy stretch, catching the heel of her pump in her hand as she begins to reminisce wistfully about sharing space with so many of her musical heroes just a week earlier. “There I am standing at the Grammys. I’m looking at Lauryn Hill, and she is doing this amazing D’Angelo tribute. She’s in my eyeline. I believe I’m in hers. I don’t think she was checking for me, but I was checking her. She won Best New Artist the year I was born, my middle name is Lauryn after her… It was all the most serendipitous full-circle moment. I was at home in London a couple of weeks ago on my sofa. Then suddenly I’m holding a Grammy, and Queen Latifah’s looking at me.”
Somehow, between feeling starstruck and in shock, Dean managed to give one of the most heartwarming speeches of the night, dedicated to a more personal hero: “I’m up here as the granddaughter of an immigrant,” she said onstage. “I’m a product of bravery, and I think those people deserve to be celebrated… We’re nothing without each other.” For Dean, the decision to speak about her maternal grandmother, who immigrated to the UK from Guyana at age 18, was natural. “I’d spoken to my mum and my auntie at home, and they said, ‘You’re a representative of this family, and you’re a representative of your grandmother’s bravery.’ It felt completely sincere in that moment to acknowledge her. I’m living the life that I’m living because of her.”
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If you’re wondering where Dean gets her courage and grit from, look no further than the women who raised her—women she describes lovingly as fearless and outspoken. “You hear us before you see us,” she says with a smile. “But they are real about building community. My auntie’s kitchen was such a place of gathering. My mum and I would always be there. They would have their glass of wine. We’d be listening to Angie Stone. They’d be giving me my musical education.”
Dean’s mother, Christine, is a lawyer who worked in child and family law before going on to become the first Black woman to be deputy leader of the UK’s Women’s Equality Party, which campaigned for gender equality. Through her, Dean learnt the importance of hard work and empowering other women. “My mum would tell me, ‘You’re going to need to be five times better.’ So that has always been in me. I’m not lazy when it comes to what I do. Everything is very intentional. I work hard. And I’m a feminist down to my toes.”
Her parents were her first teachers when it came to love. “They’ve taught me that love is a choice and that it’s work,” Dean said. “It’s not always butterflies and fairy tales. It’s consistency. It’s choosing to love that person every day, instead of choosing frustration or running away. They’ve taught me togetherness.” Their lessons on unconditional love were also exemplified by their unwavering support of their daughter’s decision to pursue music. In fact, it was Dean’s mother who suggested she apply to the famed BRIT School of musical arts, the same institution that taught singers such as Adele and Amy Winehouse.
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For Dean, the BRIT School isn’t just where she sharpened her musical senses or discovered her love of songwriting; it’s where she found acceptance and the ability to own her authenticity. “It allowed me to free myself from feeling embarrassed about who I was,” she explains. “It was so validating to be surrounded by people who thought music was cool, and wanting to shine was cool. Whereas in my previous school, people would make me feel like I was too much. And it’s like, ‘No, I’m doing too much for you. I’m actually not doing enough yet. I haven’t even gotten started’. ”
Dean credits her friendships with helping her remain grounded during this very surreal time. “I come home from doing something like the Grammys, and the debrief we’ll have is crazy,” she says. “My life can feel quite extreme sometimes, because I’m in these moments of high glamour and kind of preposterousness. I can see how people can get really lost and confused within this industry. You have to be quite mentally strong. I am so lucky that I have spaces outside of this where none of that matters. My friends care, but not more than I care about what they’re doing. My life isn’t more important than anyone else’s life. It’s just mine.”
The strong sense of self that Dean has cultivated is a superpower that runs through her work. She’s deeply confident in both her abilities and her taste, and clear-eyed about the kind of artist she’s becoming. “My purpose in music is to help people, myself included, find compassion and a deeper connection with one another. I believe people are hungry for something more honest and meaningful, something that feeds the soul. I’m attempting to provide space where that kind of connection, conversation, and joy can happen.”
Dean’s commitment to that mission is especially evident in The Art of Loving. In an era defined by maximalism and urgency, Dean leans into subtlety—allowing her voice, storytelling, and musical choices to breathe. The album moves through 12 tracks in just 34 minutes, traversing effortlessly across genres like R&B, pop, neo-soul, and beyond.
Lyrically, the album embodies Dean’s emotional intelligence; the songs refuse the toxic, lust-driven, and insecurity-soaked narratives that dominate so much of the Hot 100. Instead, she finds ways to sing about self worth: Being discerning in the face of mistreatment (“Let Alone the One You Love”) or walking away from someone you still love (“A Couple Minutes”), resulting in music that feels as good to our nervous system as it does to our ears. It’s an album for healed lover girls—the ones who’ve gone to therapy but still yearn for romance that aligns with their growth.
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“That’s where I’m at,” Dean says of the album’s healthy, nuanced perspective on love. “I’ve been in therapy for a long time. It has allowed me to have self-awareness and understand that I really don’t have time to fester in negative emotions toward love and men. It doesn’t serve me. I can be annoyed and hurt, but I try to find perspective and compassion. Reading a lot of bell hooks (pen name of American author Gloria Jean Watkins) has also given me that.”
She describes her brand of feminist romance as the kind that empowers women to do what’s best for them, while lovingly encouraging men to rise to the occasion. “‘Man I Need’ is a call to action,” Dean explains. “It’s like, ‘I know you can be the man I need if you step up to the plate and be excellent for me. Let me encourage you’.” But she had no idea the hit single would resonate with as many people as it did. “I knew that I’d made something that I was really proud of, but I also know that doesn’t necessarily translate into success,” she says. “There is so much amazing music out there that doesn’t get heard in the same way, but for some reason, people said, ‘Yeah, we like you, sis.’ And I’ve said, ‘Thank you. Me too’.” Dean’s fans include 2024’s Best New Artist Grammy winner, Victoria Monét. She says Dean “has this warmth that reaches everybody. It’s a feel-good energy from her that pulls you in. It’s refreshing to see an artist break through and shine on her own terms. She is the exact kind of artist I would love my daughter to look up to.”
While the recognition Dean has received since the album’s release has been a dream, she’s mindful not to let it impact her self-image. She deleted all social media apps from her phone after the Grammys. “I’ve been thinking about doing it for a while,” she says. “Even though the love has been overwhelming, even that is not healthy sometimes. I don’t think you’re supposed to know everyone’s opinion about you. And I’ve decided I want to live in sweet ignorance.”
The Grammy win pushed her into a new stratosphere of hashtag discourse—the zone where you become too well-liked for some people’s taste. It’s an unfortunate rite of passage that many accomplished women, especially women of colour, find themselves having to navigate. Dean understands that, to paraphrase Audre Lorde, she must define herself for herself, or be forced into other people’s fantasies for her—and be eaten alive. “I find a lot of internet discourse and those things so unproductive. I know who I am, and I know that I’m performing and creating from a pure place. You can’t please everybody. And I have such peace in that.”
Dean was, however, thrilled to find herself mentioned on an app she’ll never delete: The New York Times games. She’s been completing the mini crossword puzzle regularly for the past three years and recently noticed herself as one of the clues. “I threw my phone across the room,” she says. The clue asked for a word to describe Olivia Dean’s and Daniel Caesar’s genre of music. “I guessed wrong!” she says, laughing. “I bet it was R&B. I wouldn’t really say that, guys, but okay, sure.”
Jokes aside, Dean is still working on defining success for herself as she navigates this newfound level of celebrity. She’s never been one to get caught up in awards and acclaim. “Success to me is venues and how many people you can gather in one space,” she says. “It’s how many people you can touch.”
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By that metric, Dean has surpassed her own expectations. Tickets for her first headlining North American arena tour sold out so quickly, many to resale bots, that her OG fan base found itself priced out. It’s a problem many popular musical acts have faced, but Dean was one of the few to demand a fix from Ticketmaster, which eventually refunded fans who were overcharged by resellers and agreed to cap prices moving forward. Dean hopes it sets a precedent that helps other artists push back, especially since they don’t share in profits made on the secondary market. “There is no way that I’m going to get up on that stage and sing my heart out while somebody sits at home and makes $500, $600 off of me and you,” she says. “I want people to be able to afford to come to the show. I don’t think you need to be someone who’s got loads of money to enjoy your favourite album. Full stop.”
The tour began 22 April in the UK, with North American dates throughout July and August. Dean says fans can expect a shared experience where everyone comes prepared to sing along and dance, for a dose of fashion (she’s tight-lipped on details, but I get a wink when I ask if each city will get a custom look), and songs she hasn’t performed live before.
Performing has always been Dean’s favourite part of her artistry. “That’s where I feel the most confident and comfortable,” she says. “It’s where what I’ve made can really breathe and we can just play, and it feels fresh and exciting.” Dean’s playful spirit comes through most clearly onstage. Watching a young Black woman move throughout the world with such freedom, softness, and unburdened optimism feels comforting and, in its own way, radical. “I feel like sometimes it’s my responsibility to show that we can be that,” she says. “My joy is more powerful than whatever you think about me or how I should be presenting. I’ll always choose joy. I want to be happy. This job is too amazing for me not to enjoy it. That would be such a kicker if I’d worked this hard and then realised that I wasn’t enjoying it. I’ve got to have as much fun as possible.”
*This interview has been edited and condensed for clarity.
Photographer FELIX COOPER
Fashion Stylist ALEX WHITE
Makeup Artist CELIA BURTON using Hourglass Cosmetics
Hairstylist SOPHIE JANE ANDERSON
Manicurist ELLA VIVII using Essie
Producer MMXX ARTISTS