Kesha is no stranger to turning pain into pop—and it turns out one of her most personal breakups came to light not through a conversation, but through a song.
In a candid new interview on SiriusXM’s The Morning Mash Up, the 38-year-old “Joyride” singer confessed that she was once secretly engaged—but only realized she didn’t want to go through with it after writing a song that revealed the truth to herself.
“Basically, I find that writing songs leads me to my truth,” Kesha explained with her signature candor. “I was engaged and I didn’t wanna be anymore—and I didn’t even realize that I was gonna break up with him until I wrote a song about it.”
That moment of clarity came as a lyrical lightning bolt.
“I listened back to it,” she continued, “and I was like, ‘Oh no, I’m gonna break up with him now.’ But it led me to my truth, ‘cause I can’t lie in the song.”
For Kesha, songwriting is less about catchy hooks and more about emotional honesty. “You can’t lie in a song,” she emphasized. “A, your song will suck, but also, that’s not what it’s there for, you know?”
According to Rolling Stone, the emotional revelation found its way into “Too Far Gone,” a song featured on her 2023 album Gag Order, which was released after she ended her engagement.
The identity of Kesha’s mystery fiancé remains just that—a mystery. While she’s been linked to several men over the years, including health-tech entrepreneur Michael Gilvary, film producer Riccardo Maddalosso, and longtime love Brad Ashenfelter (whom she was last seen with publicly in 2021), she hasn’t confirmed who popped the question.
These days, the “Tik Tok” hitmaker has a refreshingly unapologetic approach to love—and luxury.
In a recent interview with PEOPLE, Kesha didn’t hold back when talking about her current romantic goals: “I have explored non-monogamy. I’ve been in love with many, many men and many, many women, and currently where I’m at is I am looking for a sugar daddy.”
And she’s completely okay with that.
“I love being able to just be open and honest about it,” she said with a laugh. “Because I’m f—ing into somebody taking care of me, putting me on a pedestal, taking me on their yacht and flying me on their plane. I’m just into it, and I will not feel shame about that.”
Reflecting on her dating history, the “Delusional” singer is ready for a serious upgrade—especially in the bank account department.
“I’ve dated a lot of very cool, very broke hipsters with very bad attitudes,” she said, rolling her eyes. “So I’m trying to swing the pendulum 180 degrees and go in the entirely opposite direction. I want someone that goes to an office building… because they own the office building.”
From ditching a diamond ring to dreaming about jet-setting with a billionaire, Kesha’s journey through heartbreak and healing has once again proven one thing: her greatest love affair might just be with her own truth—and maybe a private jet.
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