First love is always so sweet! Back in 2015, the Teen Wolf star revealed that Miley was actually his first kiss. The two met when Tyler was filming a TV show with Miley’s dad, Billy Ray Cyrus, in the early 2000s. “We kinda became ‘boyfriend and girlfriend,’ and we shared one kiss, one time,” he revealed on the Today show.
The star also had a short-lived fling with fellow Disney Channel star Dylan Sprouse. “We met at her set, I believe, and we dated. And then Nick Jonas walked by and it was over,” he told Jimmy Kimmel back in 2008. Ah, young love.
~Niley~ was the star’s first relationship that really made waves. The two were teen royalty when they first started dating in June 2006, and their relationship lasted for a year and a half before they called it quits in December 2007, inspiring Miley to write her famous hit “7 Things.”
Despite her heartbreak, she didn’t take long to move on, though, setting her sights on the older underwear model. OK, OK, Justin Gaston is not just an underwear model, he also competed on the reality show Nashville Star the same year Billy Ray hosted. Despite their five-year age difference, the couple made it last for nine months before splitting.
Is there anything better than the stars of a Nicholas Sparks movie falling in love IRL? The Last Song may have been what brought Miley and Liam together, but their relationship lasted way longer than the film’s run in theaters. The two even got engaged in May 2012, two years after the film’s premiere, though they ended up splitting by September 2013.
In December 2013, she was linked to Twilight star Kellan Lutz when Us Weekly reported they were hooking up. “They really enjoy each other’s company,” a source said. “It doesn’t hurt that he’s Liam’s pal.”
A few months later, she moved onto fellow singer Jared Leto. A source spilled to Us Weekly that neither of the celebs took the relationship too seriously, but revealed they both “like to have a good time.”
By June 2014, Miley had started dating one of her music producers after they worked together on her album Bangerz. “Everybody in her circle knows they’ve been together this whole time,” a source told Us.
The first woman that Miley was publicly linked to was model Stella Maxwell, who also dated Kristen Stewart. The two were seen making out in July 2015, but kept it casual. “I’m 22, I’m going on dates, but I change my style every two weeks, let alone who I’m with,” she told Elle U.K.
When Miley and Liam reconnected, it felt like magic — and like they must’ve been meant to be. But after getting engaged again in 2015 and exchanging vows in December 2018, the couple has once again gone their separate ways. “They have decided this is what’s best while they both focus on themselves and careers,” Miley’s rep said. “They still remain dedicated parents to all of their animals they share while lovingly taking this time apart.”
The “Can’t Be Tamed” star wasn’t slow to move on, though. Pretty much the same day that the news broke of her split, the star was seen kissing the also-recently-single Kaitlynn on an Italian beach. It’s not clear yet whether this is just a fun fling or something more, but we know one thing for sure: We ship it.