Miley Cyrus confirms she dated Dylan Sprouse — and a 2008 clip resurfaces

Miley Cyrus has finally put an old Disney-era rumor to rest: during the Hannah Montana 20th Anniversary Special, she confirmed that she dated fellow Disney alum Dylan Sprouse. The reveal, paired with a resurfaced 2008 interview clip, sent fans back to the network’s early-2000s era of crossovers, crushes and red-carpet reunions.

What was said, and when

On the March 24 special, Cyrus told host Alex Cooper, “Dylan Sprouse was my boyfriend. I think he was the cutest.” She also joked that Dylan’s twin brother, Cole, often third-wheeled their outings: “Their dad would take us to sushi… it was a two-for-one. Like, bring the brother. Hello!”

The revelation echoed a Jimmy Kimmel Live! clip from September 2008, when a teenage Dylan — then about 16 — recalled that he and Cyrus had dated when they were very young. “When I was 11 or 12, probably… We met at her set, I believe, and we dated,” he said, later quipping, “And then Nick Jonas walked by and then it was over.”

Why this matters now

The reunion special, streaming on Disney+ and Hulu, is prompting renewed interest in the Disney Channel’s tightly knit cast and the personal histories that formed off-camera. The confirmation is more than gossip: it highlights how early professional overlap — guest spots, crossover episodes and shared sets — frequently led to real friendships and relationships among young stars.

Chasing the nostalgia

  • The Suite Life of Zack & Cody and Hannah Montana crossed over during their runs, helping create the kinds of backstage moments Cyrus described.
  • The resurfaced 2008 interview gives a contemporaneous account of the young stars’ interactions, making Cyrus’s comments feel less like a throwaway memory and more like part of a documented era.

Co-stars, fans and the red carpet

The anniversary special also brought former cast members together. Cody Linley — known to fans as Hannah Montana’s on-screen boyfriend Jake Ryan — joined other alum at a Los Angeles red-carpet event ahead of the special. Emily Osment was absent due to other filming commitments.

Fans responded with waves of nostalgia on social platforms, revisiting classic episodes, GIFs and old interviews. Industry observers say the episode underscores how Disney-era stories still shape pop-culture conversation and streaming viewership.

What to watch next

The Hannah Montana 20th Anniversary Special is available to stream now on Disney+ and Hulu. Expect more resurfaced clips and throwback revelations as fans dig into archives and cast members reflect on the network era that launched careers — from Cyrus and the Jonas Brothers to Dylan and Cole Sprouse.

For viewers, the takeaway is both simple and relatable: a lot of today’s headlines start with friendships forged on set, and sometimes the juiciest details come decades later.