Nearly two decades after dominating Disney Channel, Miley Cyrus is revisiting her early fame with a candid revelation that feels straight out of a nostalgic teen drama. During the highly anticipated Hannah Montana 20th Anniversary Special, the former Hannah Montana star confirmed a long-rumored romance with Dylan Sprouse—and fans of classic Disney shows are paying close attention.
Speaking with Alex Cooper, Miley didn’t hesitate to set the record straight about their past. “Dylan Sprouse was my boyfriend,” she revealed. “I think he was the cutest.” She doubled down on the confession, addressing years of speculation with a simple, definitive statement: “It's true, confirmed.”
© FilmMagicA Sweet ‘Suite Life’ Moment Behind the Scenes
The relationship unfolded during Disney Channel’s golden era, when Miley and Dylan were both rising stars. Dylan, known for his role in “The Suite Life of Zack & Cody” alongside twin brother Cole Sprouse, crossed paths with Miley during early network projects.
Miley painted a vivid picture of their time together, highlighting just how immersive the experience felt at such a young age. “Dylan was my crush,” she shared. “Their dad would take us to sushi. I was into the whole culture, and it was a two-for-one. Like, bring the brother. Hello!”
Disney Channel Crossovers Made It Even More Memorable
Their off-screen connection overlapped with one of Disney Channel’s most iconic crossover events: “That’s So Suite Life of Hannah Montana.” The 2006 special brought together Miley, Dylan, Cole, and Raven-Symoné in a multi-show storyline that defined the era.
© FilmMagicThe relationship didn’t last long, and according to Dylan himself, another major Disney name played a role in its ending. Back in 2008, Dylan joked during an appearance on Jimmy Kimmel Live! about their brief romance. “We met at her set, I believe, and we dated,” he said, before adding with humor, “And then Nick Jonas walked by and it was over.”
© FilmMagicThat moment foreshadowed Miley’s highly publicized relationship with Nick, which became one of the defining teen romances of the late 2000s.
Where Miley Stands Today on Her Disney-Era Relationships
Looking back, Miley appears grounded and reflective about her past. Speaking on the Every Single Album podcast, she shared a mature perspective on her history with Nick Jonas. “I like Nick, I’m into him,” she said. “He’s married with children. We’re all moving on. Everything is good in the world.”
She even added a nostalgic nod to their former relationship, calling herself “Niley for life.” Today, Miley is engaged to musician Maxx Morando.
© REX Features/Shutterstock /The Grosby GroupMore Throwback Confessions From the Anniversary Special
The anniversary special didn’t stop at Dylan. Miley also reflected on her early crushes and career moments, offering fans a fuller picture of her teenage years. She admitted to having a crush on Mitchel Musso, her co-star who played Oliver on Hannah Montana. “I thought Mitchel Musso was really cute,” she said. “So I was like, ‘OK, bye, Jeff.’ It’s all about Mitchell now.”
© REX Features/Shutterstock /The Grosby GroupMiley also shared insight into how Taylor Swift became part of Hannah Montana: The Movie, praising her contribution to the film’s soundtrack. “She ate with that one,” Miley said of the song “You’ll Always Find Your Way Back Home,” calling it a timeless standout.
The Hannah Montana 20th Anniversary Special, now streaming on Disney+ and Hulu, continues to deliver these layered insights, blending nostalgia with new revelations.
