Miley Cyrus has never been one to shy away from sharing stories from her Disney Channel days, but on March 24, 2026, she surprised fans with a revelation that sent a wave of nostalgia through the internet. During the Hannah Montana 20th Anniversary Special—streaming now on Disney+ and Hulu—the pop superstar confirmed a long-rumored, secret romance from her early teen years: she dated The Suite Life of Zack & Cody star Dylan Sprouse.
“Dylan Sprouse was my boyfriend,” Miley told host Alex Cooper, her words both casual and loaded with the kind of pop culture history that defined a generation. “I think he was the cutest.” For years, rumors swirled about the pair’s off-screen relationship, but Miley put all speculation to rest: “It’s true, confirmed.”
What made this revelation even more endearing was her candid account of their time together. According to Miley, their dates often included Dylan’s identical twin brother, Cole Sprouse, making for a uniquely Disney family dynamic. “Dylan was my crush,” she reminisced. “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!”
This wasn’t just a fleeting crush hidden behind the scenes. The two, along with Cole and Raven-Symoné, shared the screen in one of Disney Channel’s most memorable crossover events: the 2006 special That’s So Suite Life of Hannah Montana. The three-episode arc brought together the casts of Hannah Montana, The Suite Life of Zack & Cody, and That’s So Raven, creating a cultural touchstone for fans who grew up in the mid-2000s.
Dylan Sprouse himself has never shied away from poking fun at his childhood romance with Miley. Back in 2008, he appeared on Jimmy Kimmel Live! and joked about their brief relationship: “We met at her set, I believe, and we dated. And then Nick Jonas walked by and it was over.” The quip became an instant classic among Disney Channel fans, and Miley’s recent confirmation only adds to the legendary status of this teenage love triangle.
But what about Nick Jonas, the third point in this star-studded triangle? Miley addressed that too, with her trademark blend of humor and honesty. On the Every Single Album podcast in June 2025, she reflected on her relationship with Jonas, which lasted from 2006 to 2007. “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 declared, with a laugh, that she’s “Niley for life.”
For those wondering how the Jonas Brothers ended up opening for Miley’s concerts during her Hannah Montana era, she offered a candid explanation: “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,” Miley explained during the anniversary special. “So I’d be like, ‘OK, well, I’ll go on tour if my boyfriend can come.’ And they’re like, ‘Cute, have your boyfriend open for the show.’ Boom.”
These revelations weren’t the only ones Miley shared during the anniversary event. She looked back fondly on her Disney Channel years, recalling not just romances but also friendships and funny moments. She confessed to a crush on her Hannah Montana co-star Mitchel Musso (“I thought Mitchel Musso was really cute,” she admitted), and even joked about her hometown crush Jeff in Nashville, whom she quickly forgot about after landing the Disney role.
Another highlight from the special was Miley’s story about Taylor Swift’s cameo in Hannah Montana: The Movie. “So the way that Taylor Swift ended up in the Hannah Montana movie was because this was kind of the beginning of her career, and they were looking for someone that would authentically—no shade, I guess—be performing in a barn. We both performed in the barn,” Miley recounted, adding high praise for Swift’s finale song, “You’ll Always Find Your Way Back Home.”
Of course, the special wasn’t just about crushes and music. Miley also reminisced about the unique perks of being a Disney star. “The coolest perk—I’m a Disney Legend now, and I have Disney Legend parking, and it says Disney Legend when I park,” she shared with a grin. “That is clutch.” She joked that she sends photos of her parking spot to friends as a cheeky reminder of her Disney legacy.
Her friendships from those days still hold a special place in her heart. Miley spoke warmly about her bond with Emily Osment, who played her on-screen BFF Lilly. “With Emily, I had what felt like a teammate, because I didn’t know exactly what I was doing,” Miley said. “I knew that we were going to have each other’s backs when it came to our timing, to our scenes, to rehearsing.”
Not all memories were glamorous, though. Selena Gomez, another Disney alum who guest-starred on Hannah Montana, recalled feeling awkward in costume. “I remember being in that blue, weird makeup,” Selena said during the special. “I remember feeling ugly in that. Because we’re, like, 15 and I want to feel pretty, and I’m like, ‘Ugh.’” Miley, ever empathetic, agreed and noted that while they played rivals on screen, “We can make amends now.”
Miley’s reflections also touched on her relationship with her father, Billy Ray Cyrus, who played her on-screen dad. The two shared a heartfelt reunion during the special, with Miley quipping about his “fresh hairdo thanks to moi.” She acknowledged the importance of their bond to fans: “I think when me and my dad are good, people, they feel better. It just feels good when the Cyruses are getting along.”
As for her personal life today, Miley is happily engaged to musician Maxx Morando. She spoke about this new chapter with gratitude: “I’ve been extremely blessed to have so much love within my family and now finding love in a different way, finding love to where I feel like I’m taking next step into my womanhood of creating a life with someone,” she shared during the special.
It’s clear that for Miley—and for fans everywhere—the Disney Channel era was more than just a launching pad for stardom. It was a time of first crushes, lifelong friendships, and unforgettable moments, both on and off screen. The Hannah Montana 20th Anniversary Special, with its behind-the-scenes stories and heartfelt confessions, offers a rare glimpse into a world where the lines between fiction and reality blurred in the most charming way. As Disney’s golden era alumni move forward in their lives, the memories—and the stories—remain as vibrant as ever.