February 2022: Conan Gray Gives Olivia Rodrigo Birthday Love
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."