Learn how love, loss, trauma and family drama marked Miley Cyrus’ transformation from wild child to first-time Grammy winner.

Even at 31, Miley Cyrus still delights in shocking audiences. After winning her first-ever Grammy — Best Pop Solo Performance for her hit song “Flowers” — on February 4, Miley took the stage to perform the post-breakup self-love anthem live on TV for the first time, pausing mid-chorus to chastise the audience for not singing along: “Why you acting like you don’t know this song,” she scolded them. She then ended her night with a second Grammy, winning for Record of the Year, before sharing a little TMI as she wrapped up her acceptance speech. “I don’t think I forgot anyone,” Miley said, “but I might’ve forgotten underwear… bye!”

It’s classic Miley. Bold and unafraid of controversy, the singer has embraced her reputation for being outspoken and unapologetic since stepping away from her old life as a Disney child star. But despite her penchant for oversharing, there’s far more to Miley than people know. “While Miley may seem like an open book, she’s very mysterious when it comes to certain things in her life,” a source exclusively tells Life & Style. Though the Hannah Montana alum “is healthier than ever today,” adds the source, she’s still working through a lot, from health problems to family drama. “Her battles with sobriety were worse than anyone knows, and her love life is more complicated than she’s let on. In fact, it took her a very long time to heal after heartbreak following her divorce” from Liam Hemsworth, 34, says the source. “There’s a lot no one knows about her.”

UPS & DOWNS
Her relationships have done a number on her — including her roller-coaster romance with drugs. Nearly a decade after she made headlines for smoking salvia leaves from a bong the week of her 18th birthday, Miley — who’s since lauded marijuana and psychedelics like ecstasy, mushrooms (which, combined with “a lot of weed” once gave her “a full anxiety attack,” she’s admitted) and ayahuasca — revealed she stopped drinking and using ahead of her 27th b-day because she was afraid of joining stars like Kurt Cobain, Amy Winehouse and Jimi Hendrix in the infamous “27 Club” of musicians who died at that age because of addiction issues.

Miley — who also suffers from tachycardia, a non-life-threatening condition that makes her heart beat faster than normal to the point she’s always “thinking about my heart,” she’s shared — then fell off the wagon during the Covid-19 pandemic. But she’s tried not to beat herself up about her on-off use. “Everyone has to do what is best for them,” she’s said.

It was perhaps harder for her to follow that advice when ending things with Liam. The duo wed in 2018 after a decade-long on-off relationship. However, the marriage ended just eight months later. Their final communication was over a text. “The last thing she said to him was that she’d always love him; it was heart-wrenching,” the source explains to Life & Style. Miley then faced criticism for dating someone else right away. “There’s a stigma of coldness for a woman who actually, really moves on,” she’s said. But that’s how she copes. “I’ve gone through a lot of trauma,” she explained in 2020, recounting facing losing her Malibu home to a wildfire, her divorce and her grandmother’s death in a short period. “I didn’t spend too much time crying over it, and it wasn’t because I was cold or trying to avoid feeling something, but it was just because I wasn’t going to change it. I tried to just continue to be active in what I can control, otherwise, you just start feeling like you’re trapped.”

Miley heals “through travel and meeting new people,” she’s explained. “As you lose one person, another person comes into your life.”

In 2021, Miley went public with Maxx Morando. She and the Liily drummer, 35, “are deeply in love, but she says she’s sworn off marriage,” the source tells Life & Style. “She’s been down that road. Besides her divorce, she has seen many close friends as well as her parents divorce.”

Instead, she wants to face challenges and joy as they come, with no expectations. Reflecting on her first Grammy win the following day, she shared how she’s grateful things happened organically. “I had all the perfect things to say, but none of them could come out in this moment of shock. I’m happy they didn’t,” Miley wrote on Instagram, “because (thankfully) prepared perfection just isn’t my story. Life is so much more exciting this way.”