Olivia Rodrigo and Conan Gray's Friendship Timeline

Olivia Rodrigo and Conan Gray are taking over the music scene one hit at a time, but we're equally obsessed with their cute friendship.

Interestingly enough, the two pop stars first connected through music. In addition to sharing the same producer Dan Nigro, they also share a love of Taylor Swift's music.

After publicly gushing about the "Cardigan" singer during various interviews and performances, Swift enlisted Rodrigo and Gray to promote her rerecorded Fearless album in April 2021.

Since then, the duo has given us various peeks of their sweet bond, including going to Halloween parties together, supporting each other's music, and hanging out at big events like the Met Gala.

"We're just pals and I think he's so brilliant," Rodrigo told Captial FM of her friendship with Gray.

Gray shared similar sentiments during an interview on Hits 1 LA with Tony Fly and Symon, saying, "She's just the best. I love her so much. We have tons of fun together. She reminds me a lot of my little sister. We very much are siblings in every single way I could think of."

In honor of their cute friendship, see more photos of them hanging out ahead.

March 26, 2021: Conan Gray and Olivia Rodrigo obsess over Taylor Swift

Ahead of the release of Fearless (Taylor's Version), Rodrigo and Gray met up for a listening session. Rodrigo shared a cute snap of them listening to the album with the caption, "Conan and Olivia listening to 'you all over me' but it's a renaissance painting."

April 8, 2021: Conan Gray and Olivia Rodrigo jam out to Fearless (Taylor's Version)

To help Taylor Swift celebrate the release of Fearless (Taylor's Version), both Gray and Rodrigo recorded short videos of them dancing and singing along to Swift's versions of "White Horse" and "You Belong With Me."

June 29, 2021: Conan Gray appears on Olivia Rodrigo's Sour Prom

During Rodrigo's Sour Prom concert, Gray made a special appearance alongside the singer's friends Lydia Night, Iris Apatow, and Madison Hu.

Sept. 19, 2021: Conan Gray and Olivia Rodrigo attend Halloween Horror Nights

The friends enjoyed a night out as they attended Halloween Horror Nights at Universal Studios Hollywood with Iris Apatow and Lexie Jayy.

Oct. 31, 2021: Conan Gray and Olivia Rodrigo spend Halloween together

The following month, Rodrigo and Gray attended Vas J Morgan and Michael Braun's star-studded Halloween party. Rodrigo, who dressed up as Elvira Hancock from Scarface, shared a video of her dancing with Gray at the party on Instagram.

Nov. 21, 2021: Conan Gray and Olivia Rodrigo attend the AMAs

Gray and Rodrigo were by each other's side as they attended the 2021 American Music Awards, where the "Drivers License" singer was up for a handful of awards. The two sat together during the ceremony and Gray could be seen giving Rodrigo a huge hug as she won new artist of the year.

Dec. 5, 2021: Olivia Rodrigo celebrates Conan Gray's birthday

For Gray's birthday on Dec. 5, Rodrigo shared a sweet birthday message on Instagram alongside photos of her and the "Maniac" singer hanging out. "happy birthday sweet cone," she captioned the post. "i love u more than anyone has loved anyone ever."

Jan. 1, 2022: Conan Gray and Olivia Rodrigo ring in the New Year

As the two celebrated New Year's Eve together, Rodrigo shared a photo of them in matching top hats, writing, "happy new year!!!! thank u guys for giving me the most exciting 365 days of my whole life. so grateful and so stoked for next year!!!!!! love u love u love u." Gray then commented on the post, writing, "everyone say thank u olivia rodrigo for the blessings she gave us in 2021."

Feb. 20, 2022: Conan Gray celebrates Olivia Rodrigo's birthday

Gray shared a sweet tribute to Rodrigo in honor of her 19th birthday. "happy bday my liv <3," he captioned a handful of photos of them together. "my heart has been looking for yours for a long long time. love u endlessly."

April 8, 2022: Conan Gray and Olivia Rodrigo share the stage together

During a stop in Vancouver for her Sour Tour, Rodrigo was joined by Gray on stage as they performed Katy Perry's "The One That Got Away."

"Being able to sing together was a really special moment," Gray told PEOPLE following the performance. "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." Though he admitted that "there's nothing in talks" about an official collaboration, they were happy to be able to share the stage together.

During their time at the concert venue, Rodrigo and Gray also filmed a viral TikTok video reenacting a scene from Twilight, which the "Brutal" singer has shown her love for on various occasions.

May 2, 2022: Conan Gray and Olivia Rodrigo attend the Met Gala

On May 2, two attended the 2022 Met Gala, marking Rodrigo's second time attending the event and Gray's first. While they didn't pose together on the red carpet, they were spotted attending a Met Gala afterparty with Maude Apatow. Following the event, Gray shared a handful of photos from the night, including one of him and Rodrigo taking a selfie in an elevator.

June 17, 2022: Conan Gray talks about his friendship with Olivia Rodrigo

During an interview with Rolling Stone, Gray opened up about his close bond with the Sour singer. "I very much value quality over quantity in my life," he said. "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."

October 2022: Olivia Rodrigo supports Conan Gray at his concert

In October 2022, the "Good 4 U" singer showed support for her friend as she attended one of his concerts alongside Madison Hu and Iris Apatow. The group sported handmade shirts, with Rodrigo's reading: "that's my f------ best friend," as a nod to Gray's song "Best Friend."

November 2022: Olivia Rodrigo and Conan Gray attend a Blackpink concert together

A month after supporting Gray at one of his shows, the friends were spotted attending a Blackpink concert together. Gray shared a cute photo of him and Rodrigo with the group with the caption, "blink 4 life 🖤💗."

Feb. 5, 2023: Olivia Rodrigo and Conan Gray attend a Grammys afterparty together

Following the 2023 Grammys, where Rodrigo presented best new artist to Samara Joy, the singer attended Universal Music Group's afterparty with Gray. The two were seen sharing a hug as they posed for cameras inside the event.

May 1, 2023: Olivia Rodrigo and Conan Gray attend the Met Gala together

In May 2023, the friends attended the Met Gala, which honored the late Karl Lagerfeld. Both Rodrigo and Gray adhered to the theme wearing black and white outfits. They also attended a handful of Met Gala parties together in N.Y.C., which Gray posted photos from on Instagram.

July 11, 2023: Conan Gray celebrates the release of Olivia Rodrigo's 'Vampire'

In July 2023, Gray posted a photo dump on Instagram, which featured a photo of him posing in front of the cover art for Rodrigo's lead single "Vampire" from her album Guts. As Rodrigo posted about the song's release on Instagram, Gray playfully commented, "edward and bela would be so proud," in reference to the lead characters from Twilight.