Olivia Rodrigo and Conan Gray's Friendship Moments Through the Years

Rodrigo and Gray first appeared on social media together in March 2021, following the release of Taylor Swift's rerecorded song "You All Over Me" off "Fearless." The two revealed their love for the award-winning singer in an Instagram post, with Rodrigo writing, "Conan and Olivia listening to 'you all over me' but it's a renaissance painting."

Touching on her friendship with Gray, Rodrigo told Capital FM on March 18, 2021, "Conan's a friend of mine, and the guy who produces most of my music produces most of his. We're just pals and I think he's so brilliant."

By April 2021, it was no secret Rodrigo and Gray were huge fans of Swift. On Instagram, Rodrigo shared a post of her and Gray reenacting moments from Swift's original music video for "You Belong With Me," which included the friends holding handwritten signs and enthusiastically lip-syncing the lyrics.

Swift herself called the pair "her two kids" in a tweet, writing about their playful collaboration, "You ok? NO cause I sent my two kids @Olivia_Rodrigo and @conangray my new version of You Belong With Me and THEY ARE SO CUTE IT PHYSICALLY HURTS ME ((Album out at midnight!))"

Rodrigo and Gray took part in spooky festivities and celebrated Halloween together in October 2021. The "Good 4 U" singer shared pictures of the night on Instagram, appearing to dress as the famous character Elvira Hancock from the 1983 film "Scarface." Along with her stunning costume and wig, Rodrigo included a video of her and Gray blissfully dancing to Chaka Khan's "I'm Every Woman."

Rodrigo showered Gray in some birthday love in an Instagram post dedicated to the "Maniac" singer for his 23rd birthday. In the post, she tagged Gray and wrote the caption, "happy birthday sweet cone. i love u more than anyone has loved anyone ever." Along with the sweet birthday message, the pictures showed moments through their friendship, including Gray surrounded by birthday banners and a balloon.

There's nothing better than starting a new year on a good note. Rodrigo and Gray brought in 2022 together and posed for a picture on the holiday. Rodrigo shared her attitude on embracing the new year, writing in the caption, "so grateful and so stoked for next year!!!!!! love u love u love u."

In February 2022, Gray posted a collage of pictures on Instagram of him and Rodrigo together for her 19th birthday. Snapshots of the pair included masked mirror selfies and matching jackets. He detailed how much their friendship means to him in the caption, writing, "happy bday my liv. my heart has been looking for yours for a long long time. love u endlessly."

As part of Rodrigo's "Sour" tour, the singer made a stop in Vancouver and shared a special moment on stage with Gray during the concert. Side by side, the two sang a stripped, acoustic version of Katy Perry's "The One That Got Away." Rodrigo shared the moment on Instagram and wrote, "ilysm @conangray singing with u is my favorite thing everrrr."

Gray reflected on their time on stage together to People, telling the outlet shortly after their performance that "she's so talented and it [was] an absolute pleasure to witness her talent in front of my eyes for the first time. I've never seen her live."