Conan Gray isn’t subtle. He doesn’t want to be. The 23-year-old singer-songwriter has built an impressive fan base—4.6 million subscribers on YouTube, where in 2013 he started posting videos of himself performing in his bedroom—thanks to confessional lyrics that read like diary entries. In his songs he’s (metaphorically) bleeding from a backstab, he’s going to wreck someone’s car, and he’s wishing his crush’s girlfriend were dead. As you get older, it’s easy to look back and feel embarrassed by the messiness and melodrama of your youth, but Gray isn’t about that. His music isn’t there to console you or coax you out of your heartbreak. It’s there to make room for the pain. It encourages you to scream, to cry, to dance the sorrow out.

“Writing music is horribly painful,” Gray tells me. He’s in Austin, thirty miles south from where he grew up in Georgetown, for the second stop on his 2022 world tour. It’s a few hours until the show at the Moody Theater, and he’s dressed casually in a pair of washed, dark blue jeans and a white muscle tank that he’s adorned with a silver bolo tie. “I think people are generally pretty dismissive of having big emotions, especially as a kid. But I’ve always been this way. I had a lot to get off my chest at twelve years old. Writing music was the most normal way for me to express it.”

Gray began posting vlogs, covers, and his first original songs to YouTube when he was a freshman at Georgetown High School. His account is dedicated almost entirely to music and lyric videos now, but for several years, it was a live journal of his life, with entries titled “Me at 17 ; For My Future Self,” “Being Mixed Race,” “18 Mistakes I Learned From by 18,” and “Getting Into My Dream School” (UCLA, in case you were wondering). 

In a 2014 livestream video chat with fans titled “Getting a Record Deal,” Gray responded to questions about whether he would release an EP or an album by saying, “Maybe just start emailing my videos to tons of record companies.” He laughs a little, then seems to consider the possibility more seriously. “That would be like a dream come true if I got a record deal. That would be everything I’ve ever wanted in my entire life.” But just as quickly, he cuts himself off. “Moving on—I’m gonna, like, start crying if I think about it.” This is Gray in a nutshell: deeply emotional, and deeply uncomfortable about it.

Born in Southern California, he spent the first years of his childhood in constant motion. There were stints in Arizona, then Hiroshima, Japan, to take care of his sick grandfather. His parents divorced when he was three years old, and they settled separately in Central Texas. Gray and his older sister often moved back and forth between their respective homes. The years that followed were spent folding stepparents and stepsiblings into his life, making and losing friends, and adjusting to each of his parents’ efforts to provide a stable life. As he summed it up in a video from 2016, it was a childhood marked by “debt, foreclosure, angry rich people, angry poor people, eviction, running from the cops, child protective services, and a lot of yelling.”

He turned to writing music as a way to cope, and he completed his first songs when he was twelve. His mother had bought him a bright blue acoustic guitar, and while he didn’t show much interest at first, he came around to it after stumbling upon a video of Adele singing “Daydreamer.” After that, music just started pouring out of him. “I don’t even know why I did it or how I knew how to do it,” he says.

Being a newcomer and one of the few mixed-race kids—his father is of Irish American heritage, his mother is Japanese—in Georgetown’s sleepy retirement community made Gray a natural outsider. He had a small, tight-knit group of friends he’s still close with today, but he often spent time alone, people-watching. “I was the fly on the wall, the observer of life. I still feel that way.”

He looked at the popular kids, the cheerleaders and football players, and filled in the details about their idyllic families and lives in his lyrics, sometimes romanticizing them, other times poking at the facade. For listeners who felt stuck in suburbia, his music offered an escape, proof that one day they’d get out of their small towns too. And for those who had already left, his songs were a gut punch of nostalgia sung over a dreamy pop production.

His senior year of high school, Gray put out a song called “Idle Town,” a slow, tender reflection on the small town he was leaving for UCLA. The song, which now has over 20 million views, eventually got the attention of Republic Records. Gray was wrapping up his first year of college in 2018 when he was offered a contract and began working with producer Dan Nigro. He dropped out of school soon after and never looked back, releasing his first EP, Sunset Season, in November of that year.

Within months, he was off on his first tour, and for the next year, he worked on writing and recording his debut album. Released in late March 2020, just as the pandemic was forcing people inside, Kid Krow debuted at number five on the Billboard 200 chart. It would be one of the biggest albums by a new artist that year. Despite the success of Kid Krow, COVID-19 precautions meant postponing what would have been a string of major milestones that year: performing at Coachella and a first world tour. But “Heather” changed everything.

The track’s video, released in August 2020, started trending on TikTok, gaining enough traction to make “Heather” Gray’s biggest hit to date. It isn’t a typical love song. It’s a wistful, jealous ode to a girl named Heather whom, as Gray writes in his liner notes, “I f—ing hated.” He continues, explaining that the person he liked was in love with her. “I had no reason to hate Heather . . . It’s this humiliating thing to admit, but it’s just true. I’m scared to see how people are going to react, because it isn’t a good thing to think something like that, but I also think it’s something that I’ve never really heard anyone admit. I’m sorry, Heather. You’re a wonderful person.”

In “Heather,” and in many of his other love songs, Gray doesn’t use specific gender pronouns when referring to his love interest. And in the music video for his song “Checkmate,” he tries to hold the hands of both a girl and a boy who are instead infatuated with each other.

This has invited much speculation on the part of fans about his sexuality, a topic he’s repeatedly showed no interest in getting specific on, even tweeting in 2018, “all y’all ever wanna do is place a label on me just let me f—in exist.”

Gray’s music is often compared to that of Taylor Swift and Olivia Rodrigo (one of Gray’s friends, and an artist Nigro also works closely with). It’s not hard to see why. Both Gray and Rodrigo have cited Swift as a major influence, and the teen duo even teamed up last year to promote the rerelease of Swift’s 2008 album Fearless.

All three are chroniclers of heartbreak, songwriters who often pivot between lovelorn angst and the thrill of a new romance on the same album. But unlike Rodrigo and Swift, Gray has never actually been in love.

It’s a confession he doubles down on with his sophomore album, Superache, out June 24. In the second track, “People Watching,” he sings, “I’ve never really been in love, not seriously.” A gentle piano plays as he belts out the chorus: “I wanna feel all that love and emotion / Be that attached to the person I’m holding / Someday, I’ll be fallin’ without caution / But for now, I’m only people-watching.”

To be clear, Gray has fallen in love—he’s had his heart broken; he’s watched relationships form and fall apart around him—but he’s never dated anyone or had his feelings reciprocated. So, as he’s done since the beginning, he’s continued to write about what he sees, telling stories about friends, inventing others about people he once knew, and unpacking emotions about the people he never professed his love to or the relationships that never became something real. “Sometimes writing music feels like the only way I’m participating in life,” he tells me.

It’s not just that things haven’t worked out before—it’s also that Gray is reluctant to let himself fall. He’s more comfortable keeping love at arm’s length, in part because the alternative seems too frightening. In the album’s eighth song, “Family Line,” he explains: “It’s hard to put into words / How the holidays will always hurt / I’ll watch the fathers with their little girls / And wonder what I did to deserve this / How could you hurt a little kid? / I can’t forget / I can’t forgive you / ’Cause now I’m scared that everyone I love will leave me.”

After the response to “Heather,” he felt more comfortable exploring his feelings without worrying if his listeners would relate to them. “With your debut, you’re just saying hello. This is more introspective,” he says, acknowledging that the writing process was more demanding this time around. Throughout the pandemic, he wrote nearly two hundred songs before whittling down the album to its final twelve tracks. “It felt like I was scraping my ribs out. I spent the last few years writing and processing. These are my secrets.”

On Superache, Gray dives deeper than before, addressing his childhood trauma around his family’s instability and his own shortcomings as someone who shuts others out, changes himself for the person he likes, or chases after a relationship that’ll never work. The end result is an impressive evolution from Kid Krow. His metaphors are sharper, his voice is stronger, and even as he sings about his disappointments, he sounds freer.

That’s Gray’s strength as a songwriter: he takes sadness that should be soul-crushing and turns it into a melody you can’t help but get swept up in. In “Disaster,” the album’s third track, he sings about a relationship that’s doomed before it starts, taking you along for the ride as the pulsing drumbeat mimics the chaos. Later, on “Memories,” he tries to get over someone who won’t let him move on as a backing chorus echoes his pleas to be set free. It’s music that could score the ups and downs of a coming-of-age film: bittersweet, yearning for the past and the present all at once.

On Kid Krow, Gray was testing the waters, giving his listeners permission to acknowledge feelings they might be ashamed of. With his follow-up, the singer seems ready to do the same for himself. It wasn’t an easy choice for him, but as he’s embarked on his first tour since the pandemic, the people singing back to him are proof that it was worth it.

“The process of recording and having to release music is horrifying,” he says. “I’m scared no one is going to relate, and it never gets better. But then touring is the moment where it becomes this massively healing process where I take these emotions that are so personal and so painful, and then I get to look out into a crowd of people who are furiously screaming every single word back to me.”