
For an artist who has been in the public eye for almost 20 years now, Miley Cyrus still manages to surprise her fans. This time, the revelation has nothing to do with a new album or reinvention but with a long-buried detail from her Disney Channel days. During the Hannah Montana 20th anniversary special, aka ‘Hannaversary,’ Cyrus revealed she had once dated Dylan Sprouse, an off-screen romance that quietly began between them when they were among Disney’s biggest teen stars. The admission adds a new layer to an era already defined by carefully managed images and highly visible young fame. Here’s a closer look at Miley’s relationship timeline, based on her statements over the years.
Miley Cyrus’s Relationship Timeline Through The Years
1. Dylan Sprouse (Mid-2000s): A Private Disney-Era Romance
Before the headlines and the public scrutiny, Miley Cyrus had a minor, quieter relationship with Dylan Sprouse. On the Hannah Montana 20th Anniversary Special premiering on Disney+, Cyrus called Dylan Sprouse her “boyfriend” from the days when their lives were set and family chaperones. At the time, Cyrus led Hannah Montana while Sprouse starred with his twin brother on The Suite Life of Zack & Cody. Their short-lived relationship never became part of the public narrative.
Hence, this confirmation is less a revelation than a reminder: There were still aspects of Cyrus’ personal life that remained private, even during the most scrutinized period of her career.
Dylan Sprouse had revealed in 2008 he dated Miley Cyrus but according to him Nick Jonas came around and they broke up! pic.twitter.com/UwwZqlRkTh
— Miley Updates (@MileyUpdates) March 24, 2026
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2. Miley Cyrus & Nick Jonas (2006-2007) – Young Love, Real Fallout
Cyrus met Nick Jonas back in the days of Disney fame, and the connection went up a notch rapidly. It is also often credited with being the reason behind her breakup with Dylan. Their relationship was intense and deeply emotional. The couple wrote songs about each other after the breakup, turning a teenage romance into pop culture lore. Cyrus has said the split “broke her heart,” leaving the fans to associate tracks like “7 Things” with Jonas. It was the first time her personal life was the direct inspiration for her music and public image.
“Literally the reason that the Jonas Brothers were on tour with me was cause Nick was my boyfriend and I wanted to not leave my boyfriend. So i’d be like okay i’ll go on tour if my boyfriend can come! And they were like cute have your boyfriend open for the show.” – Miley Cyrus… pic.twitter.com/4MePt8UmYN
— Jonas Tour Info (@JonasTourInfo) March 24, 2026
3. Miley Cyrus & Justin Gaston (2008-2009): Stepping Beyond The Disney Bubble
Miley’s relationship with Justin Gaston began soon after her breakup with Nick Jonas. Gaston, who was older and outside the Disney circle, represented a different phase in Miley’s life. The pairing attracted attention due to their 05-year age difference, but the relationship was relatively low-key. Their separation matched Cyrus’s tilt towards a more mature public persona and was a sign her Disney image was starting to fade away.
Justin Gaston (20) and Miley Cyrus (15).
Although Justin initially denied that they were dating, Cyrus confirmed it (although she didn't go so far as to confirm that they were “in a serious relationship”). The two broke up when Cyrus was 16 years old, after she left to film The… pic.twitter.com/FMv6NUxjac— ProfNet (@theprofnet) November 6, 2025
4. Miley Cyrus & Liam Hemsworth (2009-2020): A Decade Of Love, Breakups & Closure
Cyrus met Liam Hemsworth on the set of ‘The Last Song,’ and the relationship quickly became central to her personal narrative. They broke up and got together several times, even got engaged twice, and finally married in 2018. But the marriage did not last long, and the couple got divorced in February 2020. Cyrus later said their loss of the Malibu home in wildfires was a turning point, and while it brought them closer together, it also revealed cracks.
Their split in 2019 and divorce in 2020 closed the book on a chapter marked by longevity but also instability. It is still the most significant, most publicly dissected relationship Miley’s had.
However the divorce wasn't revealed publicly until weeks later.
The world found out with these photos of Miley and Kaitlynn Carter having a summer romance in Italy and the cheating accusations didn't wait. pic.twitter.com/EDTk6NXzps
— Miley Official (@MileyCyrusBz) May 16, 2023
5. Miley Cyrus & Kaitlynn Carter (2019): A Brief, Highly Public Chapter
Shortly after her separation, Cyrus was connected to Kaitlynn Carter. The relationship was big news mainly because of the timing. The two posed for photos together in Italy, days after news broke of Cyrus’ split from Hemsworth. However, Cyrus later presented the relationship as part of her own exploration and not a long-term commitment.
However the divorce wasn't revealed publicly until weeks later.
The world found out with these photos of Miley and Kaitlynn Carter having a summer romance in Italy and the cheating accusations didn't wait. pic.twitter.com/EDTk6NXzps
— Miley Official (@MileyCyrusBz) May 16, 2023
6. Miley Cyrus & Cody Simpson (2019-2020): A Fast-Paced Romance That Faded
The relationship between Cyrus and Cody Simpson was fast and furious. The two shared their relationship openly on social media and even collaborated musically together. But according to Cyrus, the breakup was down to timing. Reportedly, she admitted that they were better friends, and they didn’t want to drag out anything that wasn’t going anywhere, and put an end to all the speculations.
"Miley and i have been friends for the better part of 8 years now. Miley is a creative powerhouse, not just a musician in her own right, but as a proven writer and director." – Cody Simpson to VOGUE about Miley directing his music video ❤️ pic.twitter.com/EsSrRxQFhr
— Miley Updates (@MileyUpdates) May 24, 2020
7. Miley Cyrus & Maxx Morando (2021-Present): A Quieter Chapter
Cyrus’s recent relationship with Maxx Morando is in contrast to her past. The two have kept the relationship details under wraps, with only occasional public appearances. Reports of an engagement have come out, but neither has stooped to public spectacle. However, it is a signal that Miley’s relationship tangent points towards maturity and stability.
Miley Cyrus with fiancé Maxx Morando at the Hannah Montana premiere. pic.twitter.com/FdrZmdP55X
— Miley Edition (@MileyEdition) March 24, 2026
Relationships Shaped Miley Cyrus & Her Career
Cyrus’s affirmation of Dylan Sprouse is more than a hawk-eyed look back at an erstwhile romance. It fills in a gap from a time when her life was entirely public, or so the audience thought, until this revelation came. Moreover, her relationship timeline depicts one simple pattern: she’s just a girl trying to navigate her love life. And, when placed sideways alongside the other relationships in her life, it underlines a pattern: Each chapter did not merely influence her personal life. It had a quiet effect on the artist she was becoming.
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