Chappell Roan’s Complete Dating History

Chappell Roan, whose offstage name is Kayleigh Rose Amstutz, gave us the soundtrack of summer 2024 with her massively popular album, The Rise and Fall of a Midwest Princess. Some of her biggest hits are about relationships, love, and coming to terms with her sexuality. While the star seems comfortable talking openly about all these topics, she does keep the details of exactly whom she has dated to herself.

Here’s what is known about Roan’s dating history so far.

In a March 2023 Teen Vogue interview, Roan talked about moving to Los Angeles in the late 2010s and realizing she was more interested in women.

“[Dating a boy is] just literally not fun,” she said. “It’s not fun. It’s not hot. It’s not interesting. It’s boring.”

The singer admitted she’d had thoughts like that from a young age, but growing up in a conservative culture led her to not explore them initially.

“Maybe I like girls,” Roan said, sharing her thoughts as a kid raised in Missouri. “I was like, girls are so much prettier. Girls are nicer. I like hanging out with girls more. That was in the back of my head for all of high school. I think I like girls. I didn’t know how to deal with that part of myself except to make fun of it. Haha. It’s so funny. It’s a phase. Haha.”

Roan’s popular song “Pink Pony Club” came out in spring 2020, inspired by a night out in West Hollywood at a famous gay bar, The Alley. But she told Teen Vogue that shortly after, she ended a romance of four and a half years and moved back home with her parents. She implied she had been dating a man at the time.

In a March 2022 TikTok video, Chappell played her song “My Kink Is Karma.” She added in some commentary, saying, “I wrote this song after the worst breakup I’ve ever had. I really felt like we would be together forever. But honestly it couldn’t have ended worse. So, I ended up writing this about how I feel now.”

In an August 2023 Los Angeles Times profile, Roan revealed she was dating someone new.

“I feel scared kissing her in public,” Chappell shared. “Even though I’m in L.A., homophobia is in the back of my head. It’s liberating, but there’s a new set of problems that I didn’t know existed.”

In a performance of her ballad “Kaleidoscope,” Roan told the audience the song was about a friendship with a woman that became something more.

“Queer relationships are so difficult. They’re so complicated sometimes because you fall in love with your friends, and it’s a girl sometimes,” she shared.

In a September 2024 Rolling Stone cover story, Roan talked about being single again and trying to date.

“I met this girl that I really like, but [I] can’t commit because I feel like no one understands me,” she said. “I don’t want to date another artist because they’re fucking nuts.”

Roan added that she’s “so avoidant.”

“Because I’m just like, ‘She’ll never get me. She’ll never get it,’” explaining the person in question is “completely outside” of the music industry.

“She’s so awesome and so secure in herself and [has told me] ‘No pressure, we can just be friends if you want,’” the musician said. “I’m just running around like a chicken with my head cut off. I’m just like, ‘What? I can’t get married!’ It is that type of delusion right now.”

She also talked more about her sexual identity and being public about being a lesbian.

“I just wasn’t supposed to be sleeping with men, and now I’m a little repulsed at the thought of even kissing a guy because no one’s going to be as good as girls,” she said. “I was scared of flamboyantly gay people because I was taught that… people hate flamboyantly gay people because it exudes femininity, and people hate women. Just little things like that that you’re like, ‘Oh, my God, this is so fucked.’”

But Roan said she also felt “so uncomfortable being gay sometimes.”

“I don’t get why this is such an issue for me,” she said. “It shouldn’t be, but something’s just going on and I need to just accept that.”