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Miley Cyrus reveals ‘secret’ relationship with former Disney co-star
Home>Entertainment>Celebrity
Updated 13:34 25 Mar 2026 GMTPublished 13:26 24 Mar 2026 GMT

Miley Cyrus reveals ‘secret’ relationship with former Disney co-star

The Hannah Montana actress revealed all on a number of hot topics during the anniversary special

Joshua Nair

Joshua Nair

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Miley Cyrus opened up on one of her past relationships during her Hannah Montana 20th Anniversary Special.

2000s kids have geared up for the long-awaited return of 'The Best of Both Worlds' artist, with her special marking a sensational return for the beloved Disney character.

Hannah Montana ran for four seasons from 2006-2011, becoming one of the most memorable shows on the Disney network during the 2000s.

Whether you were a fan or not, chances are that you probably caught a glimpse of the show one time or another while growing up, and you'll know that it's responsible for shooting Cyrus to fame.

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But fans have always had a number of burning questions about the singer's time on the show, and one of these was about her relationships with fellow stars on the network.

It turns out that Cyrus 'secretly' dated one half of the most popular Disney twins of all time, years and years ago.

Miley Cyrus reunited with a number of her former Hannah Montanna co-stars last night (Amy Sussman/Getty Images)
Miley Cyrus reunited with a number of her former Hannah Montanna co-stars last night (Amy Sussman/Getty Images)

Miley Cyrus' relationship with Dylan Sprouse

Speaking to Alex Cooper during the Special, Cyrus admitted: “Dylan Sprouse was my boyfriend, I think he was the cutest.”

There had been rumours of many child stars at the time being romantically involved with each other, with the pair being in the mix, as the singer and actress added: “It's true, confirmed.”

Unsurprisingly, Cyrus said she got to spend time with both Dylan and Cole while dating the former - you'll best know the latter for his work on Disney and then Riverdale as an adult.

“Dylan was my crush,” Cyrus revealed, adding: “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!”

Cyrus admitted she dated Dylan Sprouse, pictured here with his twin Cole (Chris Polk/WireImage)
Cyrus admitted she dated Dylan Sprouse, pictured here with his twin Cole (Chris Polk/WireImage)

Their worlds would clash on Disney Channel over the years too, once in 2006 during crossover episode That's So Suite Life of Hannah Montana, and then again in 2009 on Wizards on Deck with Hannah Montana.

Both were three-episode crossover specials which will be remembered fondly by Millennials and Gen Z who were lucky enough to catch the episodes when they aired.

Sprouse had previously admitted to dating Cyrus in the past, saying they 'kind of relatively' dated, as he joked on Jimmy Kimmel Live! in 2008: “We met at her set, I believe, and we dated, And then Nick Jonas walked by and it was over.”

Cyrus admitted that she did have a thing for the Jonas Brother, before going through a dramatic break-up in 2007.

Cyrus and Sprouse shared the screen on a number of occasions on Disney Channel after dating (Disney)
Cyrus and Sprouse shared the screen on a number of occasions on Disney Channel after dating (Disney)

Speaking on the Every Single Album podcast in June, she said: “I like Nick, I’m into him. He’s married with children. We’re all moving on. Everything is good in the world.”

She revealed that the Jonas Brothers would open for her on tour because they were together at the time too, explaining: "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,

"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."

The actress herself is now engaged to Maxx Morando, a musician, and admitted she is 'extremely blessed' and looking forward to 'creating a life with someone'.

The Hannah Montana 20th Anniversary Special is available to stream now on Disney+ and Hulu.

Featured Image Credit: Dia Dipasupil/Getty Images

Topics: Miley Cyrus, Disney, Celebrity, TV and Film

Joshua Nair
Joshua Nair

Joshua Nair is a journalist at LADbible. Born in Malaysia and raised in Dubai, he has always been interested in writing about a range of subjects, from sports to trending pop culture news. After graduating from Oxford Brookes University with a BA in Media, Journalism and Publishing, he got a job freelance writing for SPORTbible while working in marketing before landing a full-time role at LADbible. Unfortunately, he's unhealthily obsessed with Manchester United, which takes its toll on his mental and physical health. Daily.

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@joshnair10

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