March 24, 2026
File this under: Disney Channel lore we did not see coming.
During the Hannah Montana 20th Anniversary Special, Miley Cyrus casually dropped a nostalgic bomb – she “secretly” dated Dylan Sprouse back in their early Disney days.
“Dylan Sprouse was my boyfriend,” Miley said. “I think he was the cutest.”
Yes, really.
Addressing years of rumours, she added: “It's true, confirmed.”
And it gets better. The relationship came with a bonus – frequent hangouts with Cole Sprouse too.
“Dylan was my crush,” she shared. “Their dad would take us to sushi… it was a two-for-one. Like, bring the brother. Hello!”
Peak 2000s energy.
Fans might remember the iconic 2006 crossover, That’s So Suite Life of Hannah Montana where Miley, the Sprouse twins, and Raven-Symoné all shared the screen – and apparently, some off-screen drama too.
Because according to Dylan, their young romance had a very Disney ending.
“We met at her set… and we dated,” he said back in 2008, before joking: “And then Nick Jonas walked by and it was over.”
Ouch.
These days, it’s all water under the bridge. Miley recently said, “I like Nick, I’m into him… We’re all moving on. Everything is good in the world.”
From secret crushes to pop culture history, one thing’s clear: Disney really was a dating universe of its own.