Conan Gray on Dating, Heartbreak, and Taylor Swift’s Influence

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From Hank Williams to Conor Oberst, every generation has its prince of sad songs, and Conan Gray is one of Generation Z’s leading contenders. “I feel everything super intensely,” says the 23-year-old singer-songwriter. “I feel like the people who listen to my music are the same way, so I don’t feel alone. I’d much rather feel everything super intensely than feel nothing at all,” he adds. Gray and I are drinking chocolate cappuccinos overflowing with whipped cream in downtown Manhattan, and he is picking at the equally caffeinated tiramisu between us. Consuming copious amounts of caffeine and exchanging stories about unrequited love is a quintessential Gray routine, familiar to his over 5 million TikTok followers or, as he calls them, “besties.”

Gray only gave songwriting a try after stumbling upon a YouTube video of Adele singing “Daydreamer,” when it occurred to him that his adolescent journal entries might be relatable. His parents split when he was three, and he grew up in Georgetown, Texas, a quiet suburb known for its booming community of retirees. “All the thrift stores were awesome,” Gray jokes. “I just love dressing like an old man who’s on a walk with his wife of 70 years.”

Surrounded by elders in his teens, Gray felt isolated—he would listen to Taylor Swift and upload self-made videos for the love songs he wrote in his bedroom. In 2017, during his senior year, he went viral on YouTube with “Idle Town,” an earnest, nostalgic tribute to home with lo-fi visuals that look like they were shot on a Sony Handycam. (One of the top comments: “Y’all don’t understand how badly I wanna be his friend.”)

After high school Gray moved to California and enrolled at UCLA, where he quickly walked out of English class after signing a record deal. “I remember going to the counselor’s office and telling them I was dropping out, and the lady was like, ‘Are you sure?’” he says. The gamble paid off. Gray moved into his own apartment in Los Angeles, met the producer Dan Nigro (who previously worked with Caroline Polachek and Olivia Rodrigo), and quickly built a loyal army of online followers. He counts Rodrigo as both a good friend and one of those followers: “I was always one of Conan’s biggest fans,” she tells me over email. “Conan really lights up every room he walks into. He’s so generous and warm with his spirit.”

When our final round of cappuccinos arrives, Gray pauses the conversation to take a photograph on his iPhone. “I have a whole process with coffee,” he explains as he tweaks the table setting slightly for Instagram. “It obviously depends where I am, but if I’m at dinner or if it’s late, it’s always a cappuccino,” he explains after photographing me with two empty coffee cups. Next week he will embark on a massive sold-out global tour, but now he has dinner plans, and the sky outside is dark. Within an hour, Gray adds another photograph to his Instagram story: more coffee.



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