Miley Cyrus Confirms Dating Dylan Sprouse During 'Hannah Montana' Filming

The pop star opened up about her childhood crush and relationship with the Disney Channel star.

Mar. 24, 2026 at 7:38pm

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In a recent interview, Miley Cyrus confirmed that she dated Dylan Sprouse while they were both starring on Disney Channel shows in the 2000s. Cyrus revealed that she had a crush on Dylan and his twin brother Cole, and that their father would take the group to sushi dinners. Dylan Sprouse also previously acknowledged the relationship in a 2008 interview.

Why it matters

This revelation provides a rare glimpse into the personal lives of two of Disney Channel's biggest stars during the network's heyday in the 2000s. Cyrus and the Sprouse twins were hugely popular with young audiences at the time, and their relationship adds an interesting layer of behind-the-scenes drama to the iconic Hannah Montana series.

The details

Cyrus made the confession during an interview for the 20th anniversary of her Disney Channel series Hannah Montana. She said that Dylan Sprouse was her "boyfriend" and "crush" during their time filming their respective shows. The pair even appeared together in crossover episodes between Hannah Montana and The Suite Life of Zack and Cody. Dylan Sprouse had previously confirmed the relationship in a 2008 interview.

  • Miley Cyrus and Dylan Sprouse dated in the 2000s while filming their Disney Channel shows.
  • In 2008, Dylan Sprouse acknowledged the relationship in an interview on Jimmy Kimmel Live.
  • The 20th anniversary of Hannah Montana was celebrated in 2023, prompting Cyrus to reflect on her past relationship with Sprouse.

The players

Miley Cyrus

An American singer, songwriter, and actress who starred in the Disney Channel series Hannah Montana from 2006 to 2011.

Dylan Sprouse

An American actor who starred in the Disney Channel series The Suite Life of Zack and Cody alongside his twin brother Cole Sprouse.

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What they’re saying

“Dylan was my boyfriend. I think he was the cutest.”

— Miley Cyrus

“I was about 11 or 12 probably...We met at her set, I believe, and we dated.”

— Dylan Sprouse

The takeaway

Miley Cyrus and Dylan Sprouse's relationship during their Disney Channel days provides a fascinating glimpse into the personal lives of two of the network's biggest stars at the time. Their candid reflections on their past romance add an extra layer of nostalgia and intrigue to the 20th anniversary celebration of the iconic Hannah Montana series.