For an entire generation of viewers, the mid-2000s Disney Channel era represented a golden age of television, defined by colorful wigs, catchy pop-rock anthems, and the inescapable charm of the "Suite Life" and "Hannah Montana" crossovers. Decades later, the star at the center of that whirlwind, Miley Cyrus, is pulling back the curtain on the behind-the-scenes reality of her teenage years. In a deeply nostalgic and revealing look at her past, the Grammy-winning singer has finally confirmed one of the internet’s longest-standing rumors: she once shared a "secret" romance with Dylan Sprouse during their shared reign at the Disney Channel.
The revelation came during the highly anticipated Hannah Montana 20th Anniversary Special, which recently premiered on Disney+ and Hulu. Speaking with host Alex Cooper, Cyrus was candid about the crushes and connections that defined her formative years under the bright lights of Hollywood. For fans who grew up watching the exploits of Miley Stewart and the residents of the Tipton Hotel, the confirmation that Cyrus and the Suite Life of Zack & Cody star were once an item served as a delightful trip down memory lane.
"Dylan Sprouse was my boyfriend," Cyrus told Cooper with a smile, officially putting an end to years of fan speculation. Recalling their early days at the network, she admitted that she found the young actor to be the "cutest" among their peer group. The relationship, while kept out of the intense glare of the paparazzi at the time, was a quintessential teenage experience. Cyrus fondly remembered spending time with both Dylan and his twin brother, Cole Sprouse, noting that their father would often take the trio out for sushi.
Cyrus joked that being interested in Dylan was something of a "two-for-one" deal, as it allowed her to immerse herself in the twins’ world. "I was into the whole culture," she explained, adding that having the brother along for the ride only added to the fun. The two stars famously shared the screen in 2006 during the iconic "That’s So Suite Life of Hannah Montana" crossover event, which brought together the casts of Hannah Montana, The Suite Life of Zack & Cody, and That’s So Raven. At the time, the young actors were at the height of their Disney fame, navigating the complexities of young love while building global brands.
Interestingly, Dylan Sprouse himself had alluded to this brief romance nearly twenty years ago. During a 2008 appearance on Jimmy Kimmel Live!, a young Sprouse mentioned that he and Cyrus had "kind of relatively" dated when they were around 11 or 12 years old. In that interview, he jokingly pinpointed the exact moment their relationship hit a wall, famously remarking that as soon as Nick Jonas walked by, his time as Cyrus’s boyfriend was effectively over.
This transition from Sprouse to Jonas marked the beginning of one of the most publicized teenage romances of the 2000s. Cyrus and Nick Jonas, often referred to by fans as "Niley," dated from 2006 to 2007, a period Cyrus looks back on with significant clarity. During the anniversary special, she revealed that the Jonas Brothers’ career trajectory was inextricably linked to their relationship. She explained that the only reason the band joined her on tour was because she couldn’t bear the thought of being away from her boyfriend. "I’ll go on tour if my boyfriend can come," she recalled telling the network and tour organizers. The result was a win-win for everyone involved: Cyrus got to stay close to Jonas, and the Jonas Brothers gained massive exposure as her opening act.
Despite the "tumultuous" nature of their teenage breakup, which Cyrus famously chronicled in her hit song "7 Things," she maintains a healthy and mature perspective on their history today. On a recent podcast appearance, she noted that she still has a fondness for Nick, acknowledging that they have both moved on to very different chapters of their lives. With Jonas now married to Priyanka Chopra and raising a family, Cyrus expressed that "everything is good in the world," even jokingly declaring herself "Niley for life" as a nod to the enduring fan base that still cherishes that era.
The anniversary special wasn’t just about the boys, however. Cyrus also took the time to reflect on the internal shifts she experienced when she first moved from her hometown of Nashville to Los Angeles to begin filming Hannah Montana. She confessed that she quickly moved on from her Tennessee crush, a boy named Jeff, once she met her costar Mitchel Musso, who played Oliver Oken. "I thought Mitchel Musso was really cute," she divulged, recalling how she mentally bid farewell to her old life to make room for her new Hollywood crush.
Cyrus also touched upon the complex dynamics of being a young woman in the industry, specifically during a conversation with Selena Gomez. Gomez, who appeared on Hannah Montana as Miley’s onscreen rival Mikayla, recalled feeling "ugly" while filming a specific episode that required her to wear blue alien makeup and a bulky costume. At 15 years old, a time when most girls are hyper-aware of their appearance, Gomez struggled with the lack of "prettiness" in the role. Cyrus resonated deeply with this sentiment, agreeing that the pressure to look a certain way was a constant companion during their Disney days. The two stars, who were often pitted against each other by the media in their youth, used the special as an opportunity to "make amends" and celebrate their shared history.
The bond between Cyrus and her primary costar, Emily Osment, was also a focal point of the retrospective. Cyrus described Osment, who played her best friend Lilly Truscott, as a vital "teammate." She admitted that in the early days of the show, she felt out of her depth, and Osment’s professionalism and support were crucial to her success. Cyrus shared a humorous anecdote about their time together, recalling a "gnarly" habit she had at Panda Express where she would pour Diet Coke over her white rice instead of soy sauce. She joked that Osment must have wondered about the "bumpkin" the network had hired, attributing her eccentric tastes to her deep Southern roots.
The special also touched on the musical legacy of the Hannah Montana franchise, including the casting of Taylor Swift in the 2009 film. Cyrus noted that Swift was cast because the production needed someone who could "authentically" perform in a barn setting—a nod to Swift’s country-pop beginnings. Cyrus had nothing but praise for Swift’s contribution to the movie, specifically the finale song "You’ll Always Find Your Way Back Home," which Swift co-wrote. Cyrus called the track a "banger" that "stands the test of time," adding that Swift truly "ate with that one."
Family dynamics, which have often been a subject of public scrutiny for the Cyrus family, were also addressed with a sense of hope and reconciliation. The special featured a reunion between Miley and her father, Billy Ray Cyrus. Miley expressed how much it meant to her—and to the fans—to see the two of them getting along. "I think when me and my dad are good, people feel better," she remarked, acknowledging the public’s investment in their relationship.
Now a "Disney Legend," a title she wears with immense pride (even boasting about her reserved parking spot at the Disney lot), Cyrus is looking toward the future. She is currently engaged to musician Maxx Morando and spoke warmly about the love she has found in this new chapter of her life. She described her relationship with Morando as a step into "womanhood," where she is focused on creating a life with a partner who truly understands her.
As she looked back on the "Team Jake or Team Jesse" debate that divided fans for years, Cyrus finally gave a definitive answer. While she appreciated the "Jake Ryan fantasy" provided by Cody Linley’s character, she admitted she leans toward Jake because Linley continues to say kind things about her in the press. It was a lighthearted conclusion to a journey that has seen Cyrus transform from a teenage idol into a self-assured woman and artist. For Miley Cyrus, the "Suite Life" and the "Best of Both Worlds" may be in the past, but the lessons learned and the love found during those years continue to shape the legend she is today.
