Miley Cyrus has basically lived ten lives since we first saw her in that blonde Hannah Montana wig. Her dating history isn't just a list of names; it’s a roadmap of her evolution from a Disney teen to a rock-and-roll powerhouse. Honestly, looking back at miley cyrus old boyfriends, it's wild to see how much each era of her music was shaped by who she was coming home to at night.
She hasn't just dated "guys." She's dated models, actors, musicians, and even a few flings that the tabloids couldn't quite put a label on. But as of 2026, things look very different for Miley than they did during the Bangerz era or those messy Malibu years.
The Nick Jonas Era: Disney’s First Power Couple
Before there was Liam, there was Nick. They were 13. It was 2006, and they were the "it" couple of the Disney Channel world. Miley once told Seventeen magazine that they became boyfriend and girlfriend the literal day they met at a charity event.
It was intense. For two years, they were inseparable. Then, they weren't.
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The 2007 breakup was brutal for fans. It gave us the song "7 Things," where Miley famously called out his "seven things" she hated about him, though she admitted she loved him, too. It was a classic case of first love meeting the pressures of global stardom before they even had driver's licenses.
Why Everyone Still Talks About Liam Hemsworth
You can't discuss miley cyrus old boyfriends without the giant, ten-year shadow of Liam Hemsworth. They met on the set of The Last Song in 2009. She was 17; he was 19.
The chemistry was instant and, frankly, a little exhausting for anyone trying to keep up. They broke up and got back together so many times between 2010 and 2012 that people lost count. They got engaged in 2012, called it off in 2013, and then—in a move that shocked everyone—reunited in 2016.
Their 2018 Nashville wedding seemed like the series finale we all wanted. Then came the 2019 split.
- The Loss: Their Malibu home burned down in the Woolsey Fire.
- The Marriage: Lasted only seven months.
- The Aftermath: "Flowers" became a global anthem about self-reliance.
Miley later told Joe Rogan that the divorce "really sucked," but not because they stopped loving each other. They just weren't those people anymore.
The Rebound Phase: Patrick Schwarzenegger and Cody Simpson
After her first major split from Liam in 2014, Miley dated Patrick Schwarzenegger. It lasted about five months. Rumor had it his mom, Maria Shriver, wasn't exactly thrilled about the "Wrecking Ball" singer's influence. They split in 2015 after he was spotted getting a bit too close to another girl on spring break.
Then there was Cody Simpson in late 2019. This one felt different because they’d been friends for a decade. They did TikTok dances, got matching tattoos, and helped each other through sobriety. But even that ran its course. Miley explained on Instagram Live that "two halves can't make a whole," and they decided to just go back to being friends.
Beyond the "Boyfriends": Exploring Fluidity
Miley came out as pansexual in 2015, and her dating history reflects that. There was the brief, high-profile fling with Victoria's Secret model Stella Maxwell. Later, right after the 2019 divorce, she spent a whirlwind month with Kaitlynn Carter.
Kaitlynn actually wrote a deeply personal essay for Elle about that time. She said it wasn't just a "summer fling"—it was a "profound journey of self-discovery." For Miley, it seemed to be a bridge between her life with Liam and her eventual independence.
Where She Is Now: The Maxx Morando Era
If you’ve been following her lately, you know the vibe has shifted. Since late 2021, Miley has been with drummer Maxx Morando. He’s low-key. He’s artistic. He actually co-produced songs on her Endless Summer Vacation and Something Beautiful albums.
In December 2025, news broke that they were officially engaged. Unlike the media circus of her past relationships, this one feels settled.
- They met on a blind date.
- He respects her need for privacy.
- He’s a collaborator, not just a "plus-one."
At the 2026 Golden Globes, Miley showed off a bespoke cushion-cut diamond ring by Jacquie Aiche. While she skipped the red carpet with him to keep the focus on her "Dream As One" nomination, insiders say she’s never been happier.
She isn't looking for "stable" in a boring way; she’s found someone who moves at her pace. The days of the "Wrecking Ball" breakups seem to be firmly in the rearview mirror.
What You Can Learn from Miley's Evolution
Miley’s journey shows that it’s okay to outgrow the people you once thought were "the one." Her relationships were public, messy, and often criticized, but they led her to a place where she could write "Flowers" and mean it.
Next Steps for You:
If you're feeling stuck in your own "on-again, off-again" cycle, take a page from the Miley playbook. Focus on your own "garden" first. Sometimes the best thing an ex can give you is the inspiration to finally stand on your own. You might find that once you stop looking for someone to complete you, you'll actually find someone who just fits.