From Tyler Posey To Cody Simpson: Inside Miley Cyrus’ Dating History

Nothing breaks like a heart, just ask Miley Cyrus. Before her days as teen star Hannah Montana and beyond, the singer has had her fair share of relationships and flings, along with true love and heartbreak. Miley, 26, dated Liam Hemsworth on and off for a decade before eventually marrying him, and was romantically linked with other actors, singers, and producers as well before and after.

Keep reading to learn all about whom Miley has dated throughout the years!

1. Tyler Posey: 2000

Tyler met Miley on the set of Billy Ray Cyrus’ show Doc in 2000, and started dating not long after. “We kinda became ‘boyfriend and girlfriend,’ and we shared one kiss, one time,” the former Teen Wolf actor recalled on the Today show, adding that it was his first kiss. “We were so damn young … I would get excited when we would hold hands,” Tyler, 27, also revealed to Entertainment Tonight.

2. Dylan Sprouse: 2005

Dylan revealed that he and Miley dated for a day or two when he was only 11 or 12 years old. “We met at her Hannah Montana set, I believe, and we dated. And then Nick Jonas walked by and it was over,” the Suite Life of Zack & Cody star joked to Jimmy Kimmel.

3. Nick Jonas: 2006-2007

Nick and Miley met in June 2006, just before he and his brothers Joe and Kevin became big stars. They dated while the Jonas Brothers accompanied Miley on the Best of Both Worlds Tour as her opening act, and broke up in December 2007. Miley penned her song “7 Things” about Nick.

4. Justin Gaston: 2008-2009

Justin and Miley met on the set of her father’s reality show Nashville Star in 2008 when he was an aspiring country singer. They dated for nine months but parted ways in June 2009 when the “Adore You” went to Georgia to film The Last Song.

5. Liam Hemsworth: 2009-2013

Liam and Miley dated on and off for years after initially meeting on the set of The Last Song in 2009. The couple made their red carpet debut in 2010, and were on and off from August 2010 to April 2011. However, the Bangerz hitmaker and Australian actor appeared to reconcile by December 2011. Liam proposed to Miley in May 2012, and then the former couple broke up in September 2013.

6: Justin Bieber: 2010

Justin went out to dinner with the “Nothing Breaks Like a Heart” singer in May 2010 and fans freaked out over the idea of them dating. Both the “Sorry” singer and Miley denied there was an attraction between them and said they were discussing “a side project” when getting dinner.

7. Avan Jogia: 2010

Avan sparked dating rumors with the Hannah Montana star in November 2010 when they were seen making out at her birthday party in Los Angeles.

8. Kellan Lutz: 2013

The Twilight star was romantically linked to Miley in December 2013. Kellan, 34, was good friends with her ex Liam, and initiated the conversation with the “Malibu” singer.

9. Jared Leto: 2014

The 30 Seconds to Mars’ frontman’s brief fling with Miley kicked off in February 2014. "They like to have a good time, they love to talk about art and music — and they're both comfortable with nudity!" a source revealed to Us Weekly. The Dallas Buyer’s Club actor and Last Song actress allegedly knew each other for a while before they started hooking up.

10. Mike Will Made-It: 2013-2014

Mike, who produced Miley’s album Bangerz, allegedly dated the singer in 2013 and 2014 following her split from Liam. Sources revealed that even though they weren’t attached at the hip, they texted all the time, and that Mama Trish Cyrus was a fan of the producer.

11. Patrick Schwarzenegger: 2014-2015

Miley met the Midnight Sun star in 2011, and had a brief fling before they began dating in late 2014. When Patrick was photographed doing body shots with a mystery girl, the “Wrecking Ball” singer called it quits in March 2015. Although the couple attempted to make amends, they ultimately broke up for good the following month.

12. Stella Maxwell: 2015

The model was romantically linked with Miley in June 2015, shortly after the singer came out as bisexual. She was spotted kissing the Victoria’s Secret angel behind a trailer on set in Hollywood. “I am literally open to every single thing that is consenting and doesn’t involve an animal and everyone is of age,” Miley said of her sexuality. “Everything that’s legal, I’m down with. Yo, I’m down with any adult — anyone over the age of 18 who is down to love me.”

13. Liam, again: 2015-2019

Liam, 29, and Miley were spotted hanging out together in April 2015 not long after Miley and Patrick broke up. Liam told Men’s Fitness that their romance was anything but fleeting when he was the November 2015 cover star. The couple was seen unloading a U-Haul truck together at Liam’s Malibu home in January 2016. Months later, Miley started wearing her original engagement ring from Liam. Since, they were inseparable and got married in December 2018, and then announced they were splitting up in August 2019, less than a year later. Two weeks after the bombshell news, the Hunger Games actor filed for divorce from Miley.

14. Kaitlynn Carter: 2019

Only a day before Miley and Liam announced their separation, Miley was spotted making out with the Hills: New Beginnings star in Lake Como. Their fling lasted only several weeks as they jetset from Italy to Los Angeles and New York. The couple broke up in late September 2019 but are “still friends” with one another.

15. Cody Simpson: 2019

Most recently, Miley was reportedly spotted kissing the singer after two highly publicized splits. They were seen together at a grocery store in Los Angeles on October 3, and an eyewitness revealed that they  “noticed people seeing them so they tried to rush out of there.” Cody, 22, referred to Miley as one of his closest friends in 2015, but they appear much closer now.