Miley Cyrus Confirms She Dated Dylan Sprouse During Disney Days

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Miley Cyrus got to live the suite life for a little bit.

Miley Cyrus revealed she secretly dated Dylan Sprouse when they both first started working at Disney Channel.

Miley Cyrus revealed on the Hannah Montana 20th Anniversary Special that she dated Dylan Sprouse, calling him ‘the cutest’ during the interview with Alex Cooper. The special premiered on Disney+ and Hulu on March 24th.

Addressing previous speculation about a relationship with Dylan, the singer of “Flowers” simply stated, “Yes, it’s true.”

Miley also remembered enjoying time with both Dylan and his brother, Cole Sprouse, while they were together—but she was only interested in one of them.

I had a crush on Dylan,” she explained. “His dad used to take both of us out for sushi, which was great because I was really interested in Japanese culture. It was a bonus to hang out with his brother too – a total package!”

Miley Cyrus achieved a unique crossover when she, along with Dylan and Cole Sprouse, appeared with Raven-Symoné in a special three-episode event in 2006. This special, titled That’s So Suite Life of Hannah Montana, blended the worlds of The Suite Life of Zack & Cody, Hannah Montana, and That’s So Raven.

Dylan, who married model Barbara Palvin in 2023, jokingly mentioned around 20 years ago that he’d briefly dated Miley Cyrus when he was a young teenager, around 11 or 12 years old.

He said they first met on set and started dating, jokingly recounting the story on Jimmy Kimmel Live! in 2008. He then teased that the relationship ended when Nick Jonas happened to walk by.

What are Miley’s current feelings about the Jonas Brothers member, considering their difficult breakup when they were teenagers back in 2007?

She revealed on the Every Single Album podcast in June that she has feelings for Nick, but acknowledged he is married with children. She stated they are both moving forward and that everything is okay.

In fact, Miley—who is now engaged to fellow musician Maxx Morando—added she is “Niley for life.” 

Disney’s Hannah Montana 20th Anniversary Special is available now on Disney+ and Hulu.

For all the revelations from the reunion special, keep reading… 

Miley Cyrus playfully revealed that when she got the role of Hannah Montana and moved to pursue her career, she ended things with a high school crush named Jeff and began dating her co-star, Mitchel Musso, who played Oliver on the show.

Miley recently revealed on Disney+’s 20th anniversary special that she had a crush on Mitchel Musso. She jokingly explained that this led her to end things with her then-boyfriend, Jeff, saying she was now happy and ‘set up’ with her new crush.

Miley joked, “Get the tea kettle for that scene!” She then explained how Taylor Swift ended up in the Hannah Montana movie. It was early in Taylor’s career, and the filmmakers needed someone who could realistically perform in a barn setting—and both of them had experience doing just that.

Miley also pointed out that Taylor wrote the song “You’ll Always Find Your Way Back Home” for the 2009 movie, and she really loved it, calling it a timeless hit. She said Taylor “nailed it” with that song.

I secretly dated Dylan Sprouse, and I thought he was really cute,” the singer told Alex Cooper. “He was my crush at the time.

Miley confirmed that the Suite Life star was, in fact, her boyfriend. She fondly recalled their dates, saying, “Their dad would often treat us to sushi. I loved the culture, and it was a great deal – like, get a brother included! It was perfect!”

Though she didn’t mention her fiancé by name, Miley alluded to her love for Maxx Morando.

I feel incredibly lucky to have so much love from my family, and now I’ve found a new kind of love that feels like a really important step forward in my life. It’s about building a future with someone, and it’s something everyone dreams of – feeling truly loved, which I’ve always experienced in different ways.

Miley asked Selena Gomez, who played Mikayla in three episodes of Hannah Montana, about her memories of filming. Miley admitted that a lot of it felt like a blur.

Selena recalled wearing the strange, blue makeup for an alien costume. She admitted feeling self-conscious about it, explaining, ‘We were just teenagers, and I wanted to feel pretty, but I didn’t at all.’

You know, Miley actually said it herself – even though we always saw their characters as rivals, she thinks they can totally make up now! It’s really heartwarming to hear, and as a fan, I’m so hoping they do!

She explained that she had the Jonas Brothers open for her concerts because she was dating Nick Jonas from 2006 to 2007.

Miley explained that she toured with the Jonas Brothers simply because Nick Jonas was her boyfriend and she didn’t want to be apart from him. She basically said she agreed to the tour only if he could come along, and they ended up letting him open for her shows.

She added, “I was always just like, ‘Well, it’ll be more fun if Nick is there.'”

Miley and her father shared a heartwarming reunion on the set of Hannah Montana. Miley joked that he’d gotten a new haircut, thanks to her!

She told Alex she was thrilled he was joining them, explaining that their connection resonated with the show’s audience. She believes that when she and her father are on good terms, it creates a positive feeling for everyone, and it’s heartwarming to see the Cyrus family getting along.

Emily Osment—who played Miley Stewart’s BFF Lilly—had a special dynamic with Miley onset.

I felt like Emily was a true partner, especially since I was still learning the ropes,” she explained. “We trusted each other to support each other with our scenes, rehearsals, and getting the timing right.

Oh my gosh, one of my favorite memories ever is when I got to go to Panda Express with Miley! She always jokes that she probably didn’t make a very good impression on me that day, but honestly, just being with her was amazing. It’s a perfect little moment I’ll cherish forever!

That was always my go-to. I used to do something kind of weird,” she said. “I loved getting plain white rice at Panda Express and pouring Diet Coke over it instead of soy sauce. It’s a funny story, actually. It explains why Emily was so surprised to meet me – she probably thought, ‘Who is this unusual person?’

As Miley quipped, “I am from the south in a way that it’s really hard to describe.”

One of the best parts of being named a Disney Legend is the parking pass! It proudly displays ‘Disney Legend’ when I park, which is incredibly convenient and helpful.

Miley playfully explained that she photographs her parking space and sends the picture to her friends as a reminder of her status. She joked that if anyone tries to give her advice, she can simply respond with ‘Disney Legend Parking,’ highlighting her successful career.

When directly asked if her character should end up with Jake (Cody Linley) or Jesse (Drew Roy), Miley responded that she couldn’t choose, saying both options were ‘out there’ and available. However, she quietly admitted she preferred Jake.

She playfully pointed out that someone was consistently praising her in the media, and she noticed. Then, with a touch of teasing, she added that Jesse hadn’t said a single positive thing about her.

The Grammy-winning artist playfully confessed she enjoys the idea of a romantic storyline with the character Jake Ryan for her role.

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2026-03-24 11:17