When Cosmopolitan1 asked me to write this cover story about my best friend Olivia Rodrigo, my first question for her was, “Can you bring a pack of cards?”
1. A few weeks after this interview, Olivia Rodrigo spent an afternoon manifesting the year ahead with Cosmopolitan editor-in-chief Willa Bennett and shared that her dream headline for this story would be “Olivia Rodrigo Does It All and She Looks Really Cool Doing It.” You can watch their vision-boarding date here.
Most of the time, Olivia and I2 are faced with the quandary of never being in the same place at the same time.3 It’s usually, I’ll see you in two months when you’re in town. When is your next break from touring? How far is Vancouver from Los Angeles, really? But the stars have aligned for this February morning in New York City, where we sit together in a hotel room, me in pajamas and Olivia in a trench coat and flare jeans, pregaming this interview with our favorite game, Nertz.
2. The “I” in this case is Olivia’s best friend, actor and Columbia University creative writing graduate Madison Hu. Of doing this story with her, Olivia later told Cosmopolitan: “I feel like I didn’t give her very eloquent answers, but she can decode my madness. She’s a million times smarter than I will ever be.”
3. Olivia spent much of the past year selling out nearly 100 live shows and recording a new album. Madison, at this point one of the only people in the world to have heard said album in its entirety, has been busy starring in the movie Sparks and alongside Steve Carell in the HBO comedy Rooster.
It’s a contentious match, and in the end, I win. I bask in my triumph while, as per her usual, Olivia is busy taking life lessons from a round of cards. “See, now this is why patience is key,” she self-soothes. “Nertz is my greatest teacher.” She’s joking, of course, but I know she’s also not entirely kidding.
Part of early adulthood is realizing you have more questions than answers, that everything you thought you’d have figured out by now remains a mystery. It’s an intimidating revelation but one Olivia leans into as she holds steadfast to a desire to learn from anything. I can attest that, just as she does in her music, she spends a lot of time in real life asking those questions—both the smaller, everyday ones and the unwieldy, daunting ones—driven by the same innate curiosity that bonded us more than a decade ago.4
4. Olivia and Madison first connected at 12 years old when they auditioned for the Disney show Best Friends Whenever. They would later be booked on the same project, Bizaardvark, and go on a two-week Disney Cruise Line trip together: “We were like Beyoncé and Jay-Z on that boat,” laughs Olivia. Their friendship, which Olivia frequently documents on Instagram, is a fan favorite. Posts of them together regularly get more than 3 million Likes.
Olivia’s willingness to admit to uncertainty, to the angst that comes with discovering who you are, is also what’s made her a voice of our generation. It started with 2021’s single “drivers license,” which she wrote during a pandemic heartbreak at 17, and continued on the emotionally raw, record-breaking album SOUR. Her second album, 2023’s GUTS, debuted at number one on the Billboard 200 and gave her tens of millions of fans exactly what they needed: a place to sit with growing pains and earnestly unravel their complexities through songs that felt at once universally true and deeply personal.
Two sold-out world tours, three Grammys, plenty of music festivals, and many global brand campaigns later, Olivia is now releasing a third studio album, you seem pretty sad for a girl so in love, on June 12.5 If SOUR came pouring out of teenage heartbreak and GUTS was produced in a pressure cooker of expectation, this one was slower, a product of constant revisions. “We really edited the hell out of this album,” she says about the body of work I’ve been lucky enough to listen to in all its many stages. There’s a new sense of levity in both her lyrics and her voice, echoing how she’s been feeling in real life. “There was so much more joy in the songwriting,” she explains. “There are some songs that are plain old sad but also some songs that are just plain old fun.”
5. When Olivia pictures her fans experiencing the new record, it’s in a very specific way, she later told Cosmopolitan: “When I was younger and an album that my friends and I were really excited about would come out, we would go to the drive-through. Get Taco Bell and sit in the parking lot and listen. If people listen to my album top to bottom in a car with their friends drinking a Baja Blast, that’s the dream.”
The album’s first single, “drop dead,” is one of the latter, fizzy and bright and full of optimism,6 an almost visceral embodiment of her famous “happy and healthy” lyrics, only this time earnest and for her and her fans. The song perfectly describes the feeling of having a brand-new crush (“The most alive I’ve ever been / But kiss me and I might drop dead”), and it has already broken records, making Olivia the first artist in history to hit number 1 on the Billboard Hot 100 Chart with all three lead singles from their first three albums. It’s a track that couldn’t have happened five years ago—nor could any of the album’s songs, really. They’re a different type of interrogation, although not necessarily full of answers to those life questions. That’s because these days, Olivia is less concerned about arriving at conclusions. Instead, she’s exploring patience (thank you, Nertz) and romantic attachment, freedom, and joy through music that feels true to where she is right now.
6. Olivia told Cosmopolitan she wrote the song after a really great first date. “I just wanted to capture that first interaction you have with someone, like, This could be the best thing ever; I’m going to tell all my friends. It reminds me of running around a city, feeling young and free. I felt that a lot while writing the album.” She took that feeling quite literally in the music video for “drop dead.” Shot at the Palace of Versailles—as in, “You lookin’ like an angel on the walls of Versailles”—Olivia frolics around the castle, headphones on, reveling in that early butterflies moment. Within the first 12 hours of the video’s release, it earned nearly 4 million views (today it has over 22 million). Olivia finished “drop dead” release week with both a surprise appearance at Addison Rae’s Coachella set and a one-night-only show for fans in Los Angeles, where she played “drop dead” twice. Naturally, the Livies ate it up.
You recently turned 23, and you were telling me the other day that it feels different than being 22.
I just feel a lot less afraid, in a good way. The year is off to a great start,7 although there was a crow in my backyard on my 23rd birthday,8 which…
7. “Awesome things keep happening to me,” Olivia later told Cosmopolitan about life at 23. “I’m Lucky Girl Syndrome-ing over here.”
8. Fans speculated that Olivia used her 23rd birthday party vibes—crowns, light-pink hues—to tease her new music. She also wore light pink to both the Grammys and a Chloé show at Paris Fashion Week. While vision-boarding with Cosmopolitan, Olivia mentioned the color multiple times. After the video was filmed, light-pink lockets were found in Los Angeles, London, Paris, and New York City, and walls were painted light pink, too.
Sometimes there’s just a bird in your backyard. What was it you said yesterday while we were playing cards?
I was looking at your cards and I lost. I was like, “It’s such a metaphor for life. If you’re too busy looking at someone else’s cards, you’re not going to look at your own.”
I swear you can take a lesson from anything. What was on your mind while making your new album?
I was really excited to write about joy, love, and passion in a way that I had never really done. Most of my big songs are about being sad, angry, heartbroken.
Do you find it harder to write about happiness?
It’s not hard to do when I’m sitting there by myself in my room, but it was never the stuff that I put out. Sometimes I listen back to it and I cringe.
Is it cringier to be happy or sad?
It’s cringier to be happy. I cringe, but I’m free. All of my favorite love songs have an element of sadness, and that’s what makes them so beautiful. A great love song has so much emotion behind it that it could go either way. I want to make love songs that you can cry to.9
9. Two of Olivia and Madison’s favorite love songs to cry to are Bright Eyes’ “First Day of My Life” and Nick Cave’s “Into My Arms.”
I remember after “drivers license,” you felt this pressure to follow it up again and again and again. How has your songwriting process changed?
We didn’t have time for revisions on SOUR. The whole world was watching. I wrote and we just fucking recorded and put it out. Then with GUTS, I was under so much pressure, like, Oh my god, I’m never going to be able to make another good song. It wasn’t even making music to make music. It was making music to please people or prove something.
What about this new album?
With this album, I actually was like, “I’m done with the sophomore one. Now I can have fun again.” I was writing songs the way I did when I was 16, purely for fun. There were some beautiful moments, like, “Whoa, it’s flowing out,” which feels like catching a butterfly10 in a net.
10. Butterflies are a motif that Olivia used throughout the promotion of her first two albums, and her updated site logo also hints at a butterfly, making fans speculate whether the insect would be a big part of you seem pretty sad for a girl so in love’s imagery, too. Livies are also convinced that a bee will be involved. The poster for her one-night-only show in L.A. featured a bee, which echoed a t-shirt she previously wore on the GUTS tour.
And how have you changed from the person who made SOUR five years ago?
I was so young then and felt like the world was on my shoulders and that I had to have everything together. I was motivated, but there was fear. Now I feel a lot more self-assured. My passion and work ethic come from a place of positivity rather than a scared mindset.
What’s allowed you to be in this new place?
For five years, I got to travel the world, perform on awards shows that had always been dreams of mine.11 It was trial by fire—if I can get through this really high-pressure situation, I can get through anything. But knowing I had people around me like you, I could go up onstage and miss a note and still be loved.
11. Some of these include her performance of “drivers license” at the 2021 Brit Awards, “traitor” at the 2021 American Music Awards, “drivers license” at the 2022 Grammys, and “vampire” and “get him back!” at the 2023 MTV Video Music Awards. She has also appeared twice on Saturday Night Live and is set to both perform and host on May 2.
Do you think you’ve gotten better at coping with anxiety?
I’m serving anxious forever. I was really nervous the first 10 shows of the GUTS tour. It was hard to be away from home and not have any sense of normalcy. I was freaking out; my nervous system was crashing out. I still get anxious. It’s just different than when I was younger.
You have a tactic for when you’re nervous during a performance. Care to share it with the class?
I always pick out a person and just sing to them; everyone else is just on the side. Your mom came to my show at The Forum in L.A., and I did the whole show just to your mom. In my head, I was like, Jennifer will love this.
What did the GUTS tour teach you about yourself?
This sounds so cheesy, but the power of music. I had never been to the Philippines12 in my life, and being able to go there and play in an arena of 55,000 people is so crazy.13 I loved watching the young girls in the crowd sing songs like “traitor.”14
12. Olivia is Filipino American, and while on set for her global Cosmopolitan cover shoot, she went out of her way to make a point to speak directly to her fans in the Philippines, sharing her favorite karaoke song (“Bohemian Rhapsody”) and saying, “Whenever I do karaoke, I think, Hell yeah, I’m Filipino!”
13. This sold-out concert at the Philippine Arena near Manila was one of the biggest of her career. Her actual biggest may have been at last year’s Lollapalooza Argentina, where she performed in front of an estimated crowd of 150,000.
14. Livies remember where they were when “traitor” dropped on October 21, 2021. Its lyrics call out a past lover able to move on after only two weeks. Five years later, with 2 billion Spotify streams, it’s still one of Cosmopolitan HQ’s favorite songs to cry to.
They’re 12 and they’re like, “You betrayed me.”
Whenever I talk to a 12-year-old girl, they tell me their story. They come up to me and they’re like, “My friend at school dropped me.” When you’re young, you take things so personally. You’re like, “It must be my fault!” When you’re older, it’s different.
What’s a boundary you’re really proud of setting recently?
I always thought a boundary was like, “Don’t do this.” But actually, a boundary is like, “If you do this, this is how I will react and protect myself.” It’s not about controlling other people, it’s about how you will respond: If somebody does this, I will be okay because I have this plan in place of what I’m going to do. It gives you so much more confidence and self-assuredness. And honestly, setting boundaries with yourself is really important, too. Saying you’re going to do something and actually doing it. For me, the phone stuff has got to go. Otherwise, I’m a brain rot person.15
15. This perhaps explains why Olivia follows zero people on Instagram despite having more than 39M followers. Although she has hinted at various times that she does have a finsta.
Fill in the blank: If I do ___ in the next year, I’ll consider the year a success.
Even if my album flops and nobody likes it, if I feel like this is real, this is me, I’m exactly where I’m supposed to be,16 then it’ll feel like success. But personally, I’d love to be surrounded by people I love.
16. These words are lyrics from the stone-cold classic “This Is Me” by Demi Lovato and Joe Jonas, featured in the Disney Channel Movie Camp Rock.
What phase of love are you in right now?
Oh my god. I’m in the most important phase, the friendship love that I’m sitting right across from. Best friend, community love. Dating is just the cherry on top.17
17. Olivia won’t officially comment on her relationship status. She was linked to actor Louis Partridge from 2023 to 2025, whom she called out as a “boy from London” she was “really, really crushing on” during her June 2025 Glastonbury Festival performance. While reflecting on that time later to Cosmopolitan, Olivia called it one of the best days of her life.
What have you learned about love lately that you wish you’d known sooner?
Patience. Things happen the way that they’re supposed to happen. It’s not supposed to be white-knuckle. But also, Madison, you’re the longest love of my life besides my parents. It’s like that book that I’m obsessed with, the Dolly Alderton book, Everything I Know About Love, I do for my female friends.18
18. Those friends, Olivia later told us, are all about group chat input: “If something is going on and we need to make a decision about a boy or something, we text the chat and go ‘Jury Duty’ and the jury commences and decides.”
When did you realize our friendship was going to be a forever thing?
The first time we got drunk together. We must have been 15 and we snuck alcohol from someone’s parents’ liquor cabinet. We put it in a water bottle.
We took “shots” out of the water bottle cap.
We were bonded forever after that moment.
I think of the way that we grew up, where we didn’t have a lot of people around us who weren’t praising us at every moment. So we do really appreciate being hard on each other.
You know me in and out and still love me anyway, and you call me on my shit. That’s a true friend. Sometimes you’re hard on me when it comes to my music.
Look, what sounds good to me sounds good to me.
I wrote a song the other day that everyone else loved and you go, “That’s so cheesy. Why would you write that?”
I didn’t say it in that manner. I said, “This is my honest listening experience. I loved this, but I was hung up on this one line because it felt cheesy to me.” Do you think we’re also hard on each other when it comes to the people we’re dating?
It’s not us judging each other. And the partner is neither here nor there. It’s us like, Who is my friend in this relationship? How does this person make her feel about herself? Is she happy?
And Is my best friend showing up as her authentic self with this person? Do you think our relationship has informed the way you’ve gone into romantic relationships?
No. We probably should integrate it, to be honest. Although, you’re a Gemini19 and three of the five guys I’ve dated in my life have been Geminis.20
19. Olivia famously calls herself a spicy Pisces—it’s one of the few consistent pieces of branding from SOUR to GUTS to you seem pretty sad for a girl so in love. But you shouldn’t rely on her to embody that sign’s trademark discretion. “I have such a big mouth,” she told Cosmopolitan. “It’s one of my worst qualities. I always forget things are supposed to be a secret. Don’t tell me anything.”
20. Olivia owns up to this pattern in “drop dead”: “Pisces and a Gemini, but I think we might go really nice together / If you let me stay the night, well, I think I might just have to stay forever.”
We really value humor with each other. We laugh like nobody’s business.
That is one of my stipulations if I want to date someone: Would they be okay sitting and hanging and playing cards with me and Madison? If they can’t hang with that, then they can’t hang with me. Your partners have not been similar to me at all.
Not in any way. But I will say I’m looking for the feeling of comfort that I feel with you. And the amount of fun that I have with you, I want to have with my partner as well.
But no guy has ever made me laugh as hard as you’ve made me laugh. Not even a quarter.
What is a goal you have for yourself that has nothing to do with what we’ve talked about so far?
Since I was really young, I’ve been grinding. I want to have more hobbies, other things that bring me passion.21 I have my friends22 and I have my work, but I feel like there’s a third other space that I can tap into.
21. A few other things that Madison and Olivia currently obsess over: Wolf Alice, Pen15, and Heated Rivalry (they were in the audience when actor Connor Storrie hosted Saturday Night Live). About Heated Rivalry, Olivia later told Cosmopolitan: “It was inspiring as a creative person. These people took a big swing—they didn’t compromise and I think that’s so rad—and it paid off.”
22. Along with Madison and Chappell, Olivia is close with Iris Apatow and Conan Gray—photos on social media show them picnicking or drinking cosmos together, as well as vision-boarding, which was the inspiration for her Cosmopolitan video with Willa Bennett.
Which hobby is first on the list?
I am literally obsessed with yoga. I try to make you go with me all the time.23
23. In terms of other potential hobbies, Olivia told Cosmopolitan, “I don’t know how to cook. I’m just eating a yogurt from the fridge, microwaving some Trader Joe’s stuff. That’s the next step of my adulthood: learning to feed myself like a real human being.”
You’re really good at it. You’re doing handstands.
With songwriting, I want to get better at it always, but there’s not really a clear trajectory. In yoga, it’s like, Oh, wow, I can touch my hands on the floor. It’s nice to have a binary: X amount of work equals Y amount of progress.
If you could go back to the day we met,24 what would you tell that Olivia? The Olivia in the yellow sweater that looked like it had mops on it.
I would tell her not to wear some of the outfits that she did. And there’s probably a boy or two that I’d be like, “Girl, you could have saved yourself the trouble.”
24. Olivia’s first thought on seeing Madison way back when at that Disney audition: “Oh my god, that girl looks so stressed. And Maddie’s first impression of me was, This girl is so afraid.”
And what do you want this next phase of your life to feel like?
I want to feel empowered, in control of my own life, calling the shots. I want to feel really creative. I’ve been getting so much joy from just being around people who are smart and cool. You are the number one person in that category. So more of that.
Lead image: All clothing Chloé. Cover image: Dress Tom Ford, ring Chanel Fine Jewelry.
Styled by Brandon Tan. Hair by Rena Calhoun for Sisley Paris. Makeup by Melissa Hernandez for Lancôme. Manicure by Yoko Sakakura for OPI. Set design by Colin Phelan. Produced by Alexey Galetskiy Productions. Shot on location at Sable Movie Ranch, provided by Métier Maison.
(Video) Director of photography: Derrick Kho.
