Miley Cyrus was in an on-again, off-again relationship with Liam Hemsworth for the better part of a decade. But throughout her personal life, she was tied to several other major stars. Here is the singer’s complete dating history explained.
“I can love me better, baby,” Miley Cyrus sings in her Grammy-winning song ‘Flowers.’ While the pop diva declares that self-love is worth more in her eyes, she is no stranger to falling in and out of love.
Since her Hannah Montana days, Cyrus has been linked with numerous stars. From Tyler Posey and Dylan Sprouse to Liam Hemsworth, the singer has done her fair share of dating around Hollywood.
As Cyrus continues excelling professionally, her personal life remains a topic of discussion. She might sing about the single life on her smash hit ‘Flowers,’ but she’s very much not single these days. One-off flings, like the one she allegedly had with Stella Maxwell in 2015, are excluded from this timeline. Cyrus herself denied rumors she was dating anyone during the time she was seen with Maxwell.
Here is Miley Cyrus’ complete dating history explained.
Tyler Posey (1999)
While working on the PAX drama Doc with Billy Ray Cyrus, Tyler Posey befriended Miley, who would “come on set every now and then and we became really good friends,” Posey told Entertainment Tonight in 2015. “We were both goofy and she was really loud, sweet, and funny… just a really cool kid.”
Posey and Cyrus eventually made it official – the couple were only nine and seven, respectively. Posey ended up sharing his first kiss with Cyrus. “We were so damn young… I would get excited when we would hold hands,” Posey said.
One thing Posey observed about Cyrus was that she already knew who she was, even at such a young age. “She was herself at seven years old. She knew who she was,” he said. “I never met anyonelike that at my age.” The two dated for two years.
Dylan Sprouse (2006)
If you didn’t know Suite Life of Zack & Cody star dated Miley Cyrus, we won’t hold it against you. Some romances fly under the radar, and some romances last a single day.
In a 2008 interview on Jimmy Kimmel Live!, Sprouse claimed he dated Cyrus for a day or so before he was blindsided by another young talent. “We met at her set, I believe, and we dated,” Sprouse said. “And then Nick Jonas walked by and it was over.”
Nick Jonas (2006-2007)
Imagine dating Nick Jonas for a moment. For Miley Cyrus, it was bliss when the two met at a charity event before heading out on the road together, with the Jonas Brothers opening for Cyrus.
Almost immediately, Jonas and Cyrus struck up a quick romance and started dating “the day we met,” Cyrus claimed in a 2008 interview with Seventeen magazine.
“Nick and I loved each other. We still do, but we were in love with each other. For two years he was basically my 24/7,” she said. “But it was really hard to keep it from people. We were arguing a lot, and it really wasn’t fun.”
When the pair broke up toward the end of 2007, Cyrus took it especially hard, even going as far as dyeing her hair black in rebellion. “On the day we broke up, I was like, I want to make my hair black now – I don’t want to look pretty; I want to look hard-core,” she recalled. “I was rebelling against everything Nick wanted me to be.”
Justin Gaston (2008-2009)
When Justin Gaston competed on the final season of Nashville Star, on which Billy Ray Cyrus was a judge, Miley Cyrus crossed paths with the promising country troubadour. But the romance drew criticism as Cyrus was only 15 when the two started dating; Gaston was 20.
In the relationship’s early days, Cyrus remained coy about dating a much older guy, as she said on Ryan Seacrest’s popular radio show. “Right now, everything is, like, really good. I haven’t really been answering the question much just because we’re just really happy with everything and the way everything has worked out,” she said.
The same conversation resulted in Cyrus addressing the controversy surrounding the age gap. “After my last two years, there’s been a lot of things that happened,” she said, “so I’ve learned just not to judge anyone and go into our friendship with an open mind and not really worry about the age or anything.”
Cyrus and Gaston dated for nine months before officially splitting up.
Liam Hemsworth (2010-2013)
Cyrus and Hemsworth’s nearly 10-year relationship began in the audition room during The Last Song. Having auditioned thousands of people to play Cyrus’ onscreen beau, the talent pool was whittled down to three. Among them was Hemsworth.
During a TikTok series in 2023, Cyrus recalled how their relationship blossomed onset. “I think one of the elements that made that movie feel so special was it was watching two very young people fall in love with each other, which was happening in real-time and in real life, so the chemistry was undeniable.”
The two became engaged in 2012 but split less than a year later.
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Patrick Schwarzenegger (2014-2015)
Reportedly, Patrick Schwarzenegger had a huge crush on Miley Cyrus before they officially became an item. “My eye, though, is set on Miley,” he once told Details in 2011. Three years later, his ambitions came true. A source revealed to Us Weekly that the two were a couple in November 2014.
Schwarzenegger, son of Maria Shriver and Arnold Schwarzenegger, dated Cyrus for just five months. The two broke up due to scheduling conflicts and it seemed to be amicable. Schwarzenegger went to study at USC, while Cyrus continued pursuing her superstar music career. “It’s not a break, It’s done,” a source told People.
“They’re just in two different places in their lives – he’s in college and she’s focused on her music and career,” the source added.
Liam Hemsworth (2016–2019)
Liam Hemsworth and Miley Cyrus reconnected in 2016 and were quickly engaged. Cyrus boasted the new ring on her Instagram.
Later, a source confirmed to People that the two were together again. “Miley is beyond happy to be engaged to Liam again,” they said. “It might seem sudden, but they have been very close for the past few months.”
With her song ‘Malibu,’ Cyrus sounded more assured in her relationship with Hemsworth. In a Billboard cover story, she admitted they needed to “refall for each other.” On writing the song, she added, “They’re going to talk about me if I come out of a restaurant with Liam. So why not put the power back in my relationship and say, ‘This is how I feel’?”
The two married on December 23, 2018, but their romance didn’t last long. Nine months later, the pair split. In a now-deleted Instagram post, Hemsworth confirmed the news, writing, “Just a quick note to say that Miley and I have recently separated, and I wish her nothing but health and happiness going forward.”
Their divorce was finalized in January 2020.
Kaitlynn Carter (August–September 2019)
Some relationships come fast and furious. That seemed to be the case between Cyrus and The Hills: New Beginnings star, Kaitlynn Carter, who began dating in August 2019. Reportedly, within a couple of weeks, Carter moved in with Cyrus.
While the pair only dated for one month, it was far from a casual fling. It was serious. But it became too serious too soon, at least according to a source close to the situation. “It was getting serious and Miley wasn’t comfortable with that,” a source claimed. “When they first got together, it was just a fun casual thing, but it ended up becoming a lot and there were big emotions attached.”
“It went from 0 to 60 and [Miley] wanted to put on the brakes. It was unexpected to end things so abruptly, but it had to be done,” the source added. “She just got out of her marriage and Miley felt like she and Kaitlynn got carried away.”
Cody Simpson (2019–2020)
Weeks after splitting with Kaitlynn Carter, Miley Cyrus linked up with Cody Simpson in early October 2019. Initially, the pair only wanted a hook-up situation. “Miley wants to show people she isn’t willing to change to satisfy others,” a source told Entertainment Tonight. “She wants to be open and honest and hook up with whomever she pleases. Right now, Cody is that person.”
But things escalated and the two dated well into 2020. During an Instagram Live, Cyrus addressed the split after a report from a “reliable source” in August 2020. “Two halves can’t make a whole and we’re individually just working on ourselves to become the people that we wanna be,” she said.
“Like everybody else at this age, we’re just deciding who we wanna be with our lives, what we wanna do with our lives,” she added.
In 2022, Simpson confirmed it was, indeed, an amicable separation. “I had just started training at the point, so my life was changing a lot and eventually I knew that I had to move back to Australia to do it properly,” he said on The Kyle and Jackie O Show.
He continued, “She was just going with her whole new album and going on tour and stuff, so it was a kind of fork in the road kind of scenario, really.”
Maxx Morando (2021–present)
Miley Cyrus and musician Maxx Morando were first seen at Gucci Love Parade in 2021 and have been keeping things pretty low-key. Since then, the pair have poured on the PDA and made countless public appearances together, including at the 2024 Grammy Awards.
In an interview with British Vogue, Cyrus mentioned the two “got put on a blind date,” she said. “Well, it was blind for me and not really for him. I thought, ‘The worst that can happen is I leave.’”
“She is very happy with him,” a source later told People. “Miley has changed a lot in the past couple of years. She seems more calm and harmonious. Everyone loves Maxx. He’s a great guy. She is very happy with him. He’s private and doesn’t like being in the press. It’s been good for her.”