The Disney Channel Years
Miley was just seven-years-old when she “dated” her first boyfriend, Teen Wolf actor Tyler Perry before dating fellow Disney star Dylan Sprouse for a whole day.
Perhaps her most memorable Disney relationship was with Jonas Brother, Nick Jonas, whom she dated from 2006 until 2007 after meeting at a charity event.
Writing in her memoir Miles To Go, the Hannah Montana star wrote: “Prince Charming and I broke up on December 19, 2007. The hardest day ever. My life felt like it had ground to a halt, but the rest of the world kept right on rolling. I was on tour. People were counting on me, but my head — no, my heart — was dizzy."
Liam: The Early Days
It was on the set of The Last Song that Miley met the man she'd end up marrying.
Miley and Aussie heartthrob Liam Hemsworth played the leading couple on-screen but rumours of a real-life romance began when PEOPLE spotted Miley, then 17, and Liam, then 20, kissing at an airport.
The couple went public at the Last Song film premiere and were even engaged in May 2012 but alas, by September 2013 they'd called it quits.
Just think, we almost wouldn't have had Wrecking Ball if it wasn't for that split. Of course, there' more on Liam later.
During the time her Bangerz album was released, Miley was renowned for her dramatic blonde haircut, twerking with Robin Thicke and a series of flings.
The We Can't Stop hitmaker was linked to Jared Leto, Kellan Lutz as well as her Bangerz album producer, Mike WiLL Made-It.
But in 2014, Miley was revealed by Us Weekly to be dating "longtime friend", Patrick Schwarzenegger. Yes, as in Arnold's son.
“They have a ton of common friends so they have run in the same circles for years,” a source told Us Weekly, however they called it quits after five months when their lives just didn't match up.
Miley also came out as pansexual in 2015 when she had a few dates with model Stella Maxwell.
Fans were delighted when romance reconcilliation rumours sprung up after Miley helped her ex Liam adopt a dog in 2015. By January 2016, Miley was wearing her engagement ring again and that summer, they were popping up on one another's Instagrams.
Miley's 2017 hit Malibu was littered with Liam references - the most obvious being that Malibu was their home and a favourite surf spot of Liam's.
The couple endured a shock tragedy in November 2018 when their home burned down in the Malibu wildfires but it was the catalyst for them to tie the knot. Miley and Liam became husband and wife in a private ceremony a month later.
However, the marriage was short-lived and the couple announced that they were breaking up for good in August the following year.
"I really do and did love him very, very, very much and still do, always will," Miley confessed in December 2020.
Post divorce dating
On the same day that her rep confirmed that Miley and Liam had split, the singer was spotted kissing Kaitlynn Carter - the ex wife of Brody Jenner who had announced her own divorce that month to.
The couple then went on an Italian holiday together and Kaitlynn even accompanied Miley to the 2019 VMAs but broke up just a month later.
"While it was short-lived, I’ll remain eternally grateful to my most recent relationship for opening my eyes to this unexplored part of myself, and for inspiring a new level of self-discovery and wonder at all the possibilities of life," Kaitlynn penned in an essay for ELLE in November 2019.
"I’ve been forced to get to know myself in a far deeper way than ever before, and not just in terms of my sexual preferences. I’ve also been forced to reckon with who I am as a person."
Longtime pals Miley and Cody Simpson were spotted kissing in October 2019 and that was just the beginning of the couple's PDA-packed romance.
They wrote songs and poems about one another and even got matching couples tattoos but by August 2020 it was over.
Confirming the news in an Instagram Live, Miley said: "We are just deciding who we wanna be with our lives, what we wanna do with our lives, and so, don’t make it some drama story if next week we’re out hanging out, getting pizza. We’ve been friends for 10 years and we’re going to continue to be friends, so just don’t make it something that it is not.”
Now she's enjoying her singledom, we hope Miley finds happiness whether she's coupled up or flying solo in the future!