Olivia Rodrigo and Conan Gray have a sweet and enviable musician friendship, but as it turns out, their beginning had a not-so-meet-cute moment.
The two singers gave fans some insight into their friendship dynamic this week in an Interview Magazine article published on August 15, 2025. The interview coincided with Gray’s fourth studio album drop — Wishbone — and the pair detail the creative process. Rodrigo joked that she’s a “bad interviewer” because there’s “so little that I actually don’t know about this album process.”
Conan Gray and Olivia Rodrigo are seen outside Carbone on May 01, 2022, in New York City.Gotham
In true bestie fashion, they took fans back to 2020, during the COVID-19 lockdowns, and how their friendship first blossomed, despite a teeny tiny misunderstanding. Rodrigo was working on her debut album, Sour, with producer Dan Nigro, while Gray was working on his second album with him. Gray said that since it was during the pandemic, “we literally saw nobody even vaguely in our age range for an entire year,” until one day he saw Rodrigo leaving the studio.
“I think you were kind of midway through Sour?” Gray recalls. “I was walking in and I remember seeing you and being like, ‘Oh my god, a person.’”
Gray and Rodrigo both joked that the only person they saw outside of their families was Nigro. Then Gray asked Rodrigo if he should talk about “the text,” which turned out to be Rodrigo asking Gray if he wanted to “go on a COVID walk one of these days.” Gray’s response? Absolutely nothing.
“You gave me your number, and I had a childhood neighbor growing up named Olivia,” Gray explained. “So I received a text from an Olivia a week later and it’s like, ‘Hey, want to hang out?’”
He continued: “And I was like, ‘What? Why is my childhood neighbor texting me to hang out in Texas? She knows that I moved. Does she think I’m back home or something?’ I literally was so weirded out because this was my neighbor. Like, we weren’t super close friends or anything. So I just ignored it fully.”
