Olivia Rodrigo and Conan Gray are two of music’s biggest stars thanks to their killer songwriting chops—and they just so happen to be best friends, too. The pair initially met on the internet “just like everyone else our age,” according to Conan, and they openly mused about their mutual love for Taylor Swift on their social timelines as teens. Since then, Liv and Conan have danced at awards shows together, taken vacays with their besties Iris Apatow and Madison Hu, and even sparked collaboration rumors. Now, if that’s not a friendship worthy of a Grammy-nominated album, I don’t know what is.
Ready to revisit the best moments of Olivia Rodrigo and Conan Gray’s friendship timeline? Go back to the beginning with all the details below.
Olivia wrote and performed “All I Want” for High School Musical: The Musical: The Series, and the track eventually went viral on TikTok. In a June 2022 interview on The Today Show, Conan revealed that his friendship with Liv started via DM when he first heard it.
“I remember I messaged her because I heard a song she’d written years ago called ‘All I Want’ and I was like, ‘That’s the best song I’ve heard in a very long time,’” he told host Hoda Kotb.
Taylor Swift enlisted Olivia and Conan to tease Fearless (Taylor’s Version) on April 9, 2021. The duo paid homage to Taylor’s music video for “You Belong With Me” with handwritten signs.
Olivia dropped her iconic Sour prom special, which featured Lydia Night, Conan, Madison, and Iris.
The duo attended a Halloween party, where they danced the night away as Elvira Hancock from Scarface and Rodrick from Diary of a Wimpy Kid.
Olivia attended her first American Music Awards, and ofc, her bestie Conan was her date for the evening.
“The girls r girling” with Conan, according to an O-Rod photo dump.
A few days later, the “traitor” singer posted birthday wishes for Conan on Instagram with an adorable message that'll make your heart swell. “Happy birthday sweet cone. i love u more than anyone has loved anyone ever,” she wrote.
Olivia and Conan rang in 2022 together, complete with top hats and party horns. 🥳
Liv, Conan, Iris, and The Kid Laroi had a fun-filled day at Disneyland. That roller coaster pic? Honestly, hang it in the Louvre.
Conan rang in Olivia’s birthday with a carousel of pics, writing, “Happy bday my liv <3 my heart has been looking for yours for a long long time. love u endlessly.”
Liv and Conan recreated an iconic scene from Twilight during her SOUR Tour stop in Vancouver (and, yes, I’ve been replaying this TikTok ever since):
Conan also came out as a special guest and *flawlessly* covered “The One That Got Away” by Katy Perry with Olivia. “Ilysm @conangray singing with u is my favorite thing everrrr,” Olivia wrote on Instagram.
Liv and Conan were spotted grabbing dinner at Carbone the night before the Met Gala.
Ahem, a moment of silence for the duo’s slay on the Met steps:
Conan gushed about his friendship with Olivia in a conversation with Rolling Stone, saying, “I very much value quality over quantity in my life. With Olivia, she’s someone that I just adore. And it’s always nice to have friends that you can depend on. [Fame] is a very confusing thing, and it’s nice to have people that you can relate to and find comfort in.”
Conan dropped his sophomore album, Superache, that same month, featuring a song called “Best Friend.” Fans theorized that the track was partly inspired by his friendship with Olivia.
Not! To! Mention! The official lyric video is formatted to look like Instagram DMs, which is how the duo initially connected in 2020. Cute!
While fans began theorizing (and manifesting) a musical collaboration between Conan and Olivia, he put rumors to rest during an interview with PopBuzz(now called Capital Buzz). The main theory at the time was that they wrote a track called “Dreamlike” together. “People love to make things up and then nobody cares, on the internet, if something is true or not,” Conan explained. “That song doesn’t exist. I’m sorry to let people down.”
Olivia, Conan, and Madison had a chill beach day in Malibu.
Olivia, Madison, and Iris pulled up in chic DIY shirts to support Conan during his Superache Tour. Olivia’s shirt referenced the lyrics to his track “Best Friend.”
Conan and Olivia hit up Universal Music Group’s Grammys after-party at Milk Studios in L.A.
Conan also dropped a sweet message for Olivia’s 20th birthday:
The pair attended the Met Gala and its respective after-parties. Allow me to present alllll the content that came from the first Monday in May:
![conan gray olivia rodrigo](https://irss.plus//node/data/uploads/original/image/2b/e9/2be9c25b5bd8e0a4f64f6b156f4979e9.avif "The 2023 Met Gala Celebrating "Karl Lagerfeld: A Line Of Beauty" - Red Carpet")
Olivia released “vampire,” the lead single for her album GUTS and celebrated with a cute (since-deleted) Instagram post. Conan showed his support in the comments, writing, “I, dare say, streamed ☝️😌.”
Conan posed with a promotional pic of Olivia out in the wild later that same month.
Liv and Conan are back at it again with another TikTok—this time promoting her song, “get him back!”
The pair posed for cute pics at the premiere of The Hunger Games: The Ballad of Songbirds and Snakes.
![conan gray olivia rodrigo](https://irss.plus//node/data/uploads/original/image/f5/69/f5696e9cfda9213d39a6b7f5fc53823b.avif ""The Hunger Games: The Ballad Of Songbirds & Snakes" Los Angeles Premiere - Arrivals")
The duo attended a VIP dinner for GQ’s Men of the Year Party at the Chateau Marmont in L.A., and Liv posted some Polaroids with Conan on Instagram.
“Konin” and Liv took London later that month (and she left a cheeky comment on his post)!
Conan and Olivia posed together in matching florals at Variety’s Hitmakers brunch.
A few days later, Conan, Madison, and Iris hung out with Olivia’s then-boyfriend Louis Partridge and watched her set at iHeart Radio’s Jingle Ball in New York.
Conan enlisted Olivia and another friend to help tease his third album, Found Heaven. The trio posed by holding up “1-3-1” with their fingers, and the “Heather” hitmaker announced Found Heaven on January 31.
Conan sang some of Olivia’s songs during a livestream with fans (he’s just like me, for real).
During an interview, Conan revealed that “All-American Bitch” and “Lacy” are some of his favorite songs by Olivia. He also dished that they “bonded” over his 2019 track, “Lookalike.”
Conan, Olivia, and Madison were spotted out and about in NYC’s West Village on April 7.
Two days later, he attended Olivia’s GUTS Tour at Madison Square Garden, where he fully jammed out with Joe Locke and Kaia Gerber.
The crew also attended an after-party, according to fan accounts.
She also posted a photo dump after closing the first leg of her Guts Tour in NYC, featuring this pic of Conan referencing a TikTok user who called her “Olivia Rodriguez...that little Mexican girl that be crying.”
Liv and Conan took on Coachella on the 13th. Olivia posted a clip of her riding a golf cart with Conan on the festival grounds, and the duo was spotted dancing in the crowd of No Doubt’s set after Olivia joined Gwen Stefani for a duet onstage.
Olivia commented “star as fuck” on a Lollapalooza recap Conan posted, and all we can say is, saaaaaaaaaame.
Olivia, Louis Partridge, Maisie Peters, and Joe Locke attended Conan’s last Found Heaven Tour show in Manchester.
On November 12, Liv posted cute photo booth pics with Conan—and a selfie with Joe Locke—in her latest photo dump.
In honor of Conan’s birthday, Olivia posted some sweet snaps on her Instagram Stories to commemorate the occasion. “Happy birthday to my dearest cone ❤️❤️❤️ nobody more special in this world,” she wrote alongside a pic of the “Heather” hitmaker blowing out candles on his birthday cake.
On another slide, she deemed him her “Bestie for the restie” and then shared a silly pic from one of their many UK trips.
Olivia and Conan both played the Governors Ball music festival in New York City, where they each shouted each other out onstage. Conan also told Seventeen he was most excited to watch Liv’s set that weekend.
Later that month, Liv celebrated moving out of her NYC apartment by posting selfies she took in the hallway of her building. Of course, Conan made several appearances.
Conan, Liv, Addison Rae, Chappell Roan, and Madison Hu attended Lady Gaga’s Mayhem Ball concert at the Kia Forum in L.A.
The besties also released a cute set of friendship necklaces on their respective merch stores, but they have (very sadly!) sold out.
Olivia interviews Conan to promote his album, Wishbone, for Interview magazine, and it’s just full-on bestie vibes. “I mean, there’s literally nobody on earth that I have asked more questions to about this album than you. We literally made this album together, literally down to picking singles, down to production elements, literally everything,” Conan said at the time.
Olivia attended Conan’s Wishbone World Tour, where they split a wishbone evenly. They’re soulmates, for real!
Conan also appeared on Blind Date with Cosmopolitan, where he revealed Olivia’s favorite song off of Wishbone is “My World.” (To which we say: taste!)
Conan and Olivia are photographed with Role Model at Sir Lucian Grainge’s 2026 “Music Is Universal” Artist Showcase ahead of the Grammys.
The duo are only two of the massive musicians who covered Cosmopolitan’s Sound of Now issue, which dropped during Grammys season.
They also attended Charli xcx’s Grammy after-party at the Chateau Marmont in L.A. with Laufey and Tate McRae!
Conan supported Olivia’s new single, “drop dead,” on his Instagram Stories, writing, “Just so we’re clear this is the only song that has touched my ears since midnight of two days ago (i love you @oliviarodrigo @dan_nigro).”
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