Entertainment Music Conan Gray Says He's 'Never Actually Dated Anyone' But Has 'Been Heartbroken': 'Makes Me Nervous' Conan Gray told GQ he feels "almost ready" to be in a relationship for the first time By Rachel DeSantis Published on February 24, 2022 01:25 PM Share Tweet Pin Email Trending Videos Conan Gray. Photo: Rodin Eckenroth/Getty Conan Gray may have made a career of writing songs about heartbreak, but according to the star, he's never actually been in a relationship. The "Maniac" singer, 23, revealed in a new interview that while he's fallen for plenty of people, his anxieties surrounding dating have prevented him from ever taking things to the next level. "You will probably be surprised to learn that I've never actually dated anyone. It's embarrassing! Dating makes me nervous," he told GQ. "All my best friends are dating people, though, so I live vicariously through them. I've been heartbroken, obviously. I've been in love with people, but they haven't loved me back." Gray explained that while still in high school, he fell in unrequited love with someone "who ended up destroying him," and revealed that that person inspired the viral hit "Heather," as well as much of his first album Kid Krow. RELATED VIDEO: Conan Gray Opens Up About Taylor Swift, His TikTok Hit and Embracing His Japanese Heritage He noted that he still writes songs about the person, and remains a romantic at heart, often finding himself falling fast and hard. "I meet a person one time, and then I'm in love with them. Someone will look at me, and I'm like, 'I guess we're getting married!'" he said. "That's how I've always been. I think that's fun. My best dating advice for you? You should let yourself fall deeply in love with random people." Conan Gray Opens Up About Taylor Swift, His TikTok Hit and Embracing His Japanese Heritage Given all he's been through, Gray said he feels "almost ready" to be in a relationship, and is most attracted to smart, nerdy and passionate people who are "open to still learning about themselves." "I think a lot of my anxiety around dating has come from my fear of being heartbroken again because I was so sad for so many years about the first one," he said. "I get so freaked out by the idea of dating someone that I will drop people because I'm terrified that they're going to hurt me." Still, he acknowledged that he's working on accepting the fact that dating "can be casual," and that not all crushes equate to marriage. "That was a big realization for me this year," he said. "I'm still working through it." Conan Gray Says His Forthcoming Album Kid Krow Was Inspired by His 'Pretty Tough' Childhood Gray, who named one of PEOPLE's Ones to Watch in 2020, told PEOPLE that year that he was still surprised by his own success, and said he has "deeply rooted imposter syndrome." "I let it stay surreal, because I think the moment you let it sink in, it starts to become a little bit too much," he said. "So I'd rather just be kind of aloof, and realize that this is such a miraculous, incredible thing that happened."