Miley Cyrus didn’t hold back while reflecting on her Hannah Montana days.
During the sitcom’s 20th anniversary special, Cyrus sat down for an interview with Alex Cooper. While discussing her time as the fictional pop star, Cyrus spilled the tea on her past romances.
She confirmed her past relationship with fellow Disney Channel star Dylan Sprouse, best known for The Suite Life of Zack & Cody.
“Secretly, okay, Dylan Sprouse was my boyfriend. I think he was the cutest,” she said.
Shortly after Cyrus’ confession, an old clip of Sprouse discussing their relationship went viral.
Dylan Sprouse opened up about dating Miley Cyrus
Image credits: Disney+
In the anniversary special, Miley Cyrus, 33, revealed she had a crush on Dylan and confirmed they briefly dated.
Despite sharing fond memories of time spent with Sprouse, his twin brother Cole, and their father, Cyrus did not explain why the relationship ended.
However, Sprouse offered an explanation during a 2008 appearance on Jimmy Kimmel Live!, blaming one of his Disney co-stars.
“We met at her set, I believe, and we dated,” the actor said.
Image credits: Francois Durand/Getty Images
He was likely referring to the Disney Channel crossover episode That’s So Suite Life of Hannah Montana, which marked their first on-screen appearance together.
“And then Nick Jonas walked by, and it was over,” he added.
Although he was joking, Sprouse implied that Cyrus dumped him for Jonas, who starred in Disney’s Camp Rock (2008) and the sitcom Jonas.
Miley Cyrus talks about dating Nick Jonas in the Hannah Montana special
Image credits: Kieran Frost/Getty Images
According to reports, Cyrus and Jonas dated between 2006 and 2007.
The Wrecking Ball singer also revisited her relationship with Jonas during the special.
Cyrus revealed that during her first major tour in 2007, she specifically asked Jonas’ band to open for her because they were dating at the time.
“Literally, the reason that the Jonas Brothers were on tour with me was because Nick was my boyfriend, and I wanted to not leave my boyfriend,” she said.
During an appearance on the Every Single Album podcast in June 2025, Cyrus said she was heartbroken after their breakup, suggesting Jonas had dumped her.
Hannah Montana special has fans digging up old Disney drama
Image credits: Rob Hoffman/Getty Images
Because Cyrus, Nick Jonas, and Dylan Sprouse were all Disney Channel regulars in the late 2000s, fans were confused by the timeline of her dating history.
“I need the Miley/Dylan relationship timeline,” one fan wrote on X.
Another commented, “Just when we thought we already knew everything and there’s no more lore to uncover.”
Image credits: Amy Sussman/Getty Images
Fans also pointed out that Selena Gomez, who appeared in the special and played Miley’s rival in Hannah Montana, reportedly dated Nick Jonas as well.
“Disney star lore is crazy because what do you mean Miley Cyrus dated Dylan Sprouse and Selena Gomez had a crush on Cole Sprouse, but her first kiss was Dylan Sprouse, and they both dated Nick Jonas,” they wrote.
Despite renewed attention on their early dating lives, the trio appears to have moved on from the drama.
Sprouse, 33, has since married model Barbara Palvin. The couple began dating in 2018 and eventually tied the knot in July 2023.
Jonas, 33, is also married and has one daughter with his wife, Priyanka Chopra.
Cyrus was married to Liam Hemsworth, but they divorced in 2020. Since 2021, she has been in a relationship with Maxx Morando, and the two reportedly got engaged in December 2025.
The Hannah Montana 20th Anniversary Special is streaming on Disney+.
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