Miley Cyrus dropped a dating bombshell during the Hannah Montana 20th Anniversary Special, confirming she dated fellow Disney Channel star Dylan Sprouse during their teenage years.
The Revelation
During the special, which premiered yesterday on Disney+, Cyrus casually revealed new details about her relationship with Dylan Sprouse from The Suite Life of Zack and Cody.
MILEY CYRUS DATED DYLAN SPROUSE WHEN THEY WERE KIDS???????? omg
— rodri 🌙 (@perchin9999) March 24, 2026
The two young stars dated while both were rising to fame on Disney Channel in their respective series—Hannah Montana and The Suite Life of Zack and Cody.
What Miley Cyrus Said
Cyrus described Dylan Sprouse as both a former boyfriend and an early crush, confirming decades of fan speculation from the height of the Disney Channel era.
“Dylan Sprouse was my boyfriend … I think he was the cutest … Dylan was my crush,” she said during the special.
She added: “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!”
lol imagine if miley cyrus and dylan sprouse went on a double date back then with his brother cole and selena gomez? they would have made the teen magazine front covers. https://t.co/v26H9agkam
— 🌸 (@musicmovies7) March 25, 2026
The comment reveals that their relationship involved spending time with both Sprouse twins and their father, creating a group dynamic in which Miley would see Dylan while also hanging out with his twin brother, Cole.
The Miley Cyrus Timeline
All three Disney Channel stars were approximately 16 years old when Hannah Montana: The Movie premiered in April 2009.
This places the relationship during the height of both shows’ popularity when all three were navigating:
- Fame and busy production schedules
- Teenage relationships in the public eye
- Rising celebrity status on Disney Channel
The Special Features
The Hannah Montana 20th Anniversary Special is hosted by Alex Cooper from the Call Her Daddy podcast, bridging early 2000s Disney Channel fans with those who follow Cyrus’s adult career.
Includes:
- Exclusive interview with Miley Cyrus
- Musical performances
- Never-before-seen archival footage
- Retrospectives on the series
- Recreated sets (Stewart family living room, Hannah’s closet)
The Premiere Event
The El Capitan Theatre in Los Angeles hosted the world premiere with Cyrus reuniting with co-stars:
- Jason Earles (Jackson Stewart)
- Moisés Arias (Rico)
- Shanica Knowles (Amber)
- Anna Maria Perez de Tagle (Ashley)
- Cody Linley (Jake Ryan)
- David Archuleta (himself)
Notable Absence: Emily Osment, who played best friend Lilly Truscott, missed the event due to filming Georgie & Mandy’s First Marriage.
Disney Archives Display
Walt Disney Archives showcased iconic memorabilia at the premiere:
- Two Hannah Montana costumes
- Miley’s guitar from the series
- Hannah’s iconic blonde wig
The blonde wig remains the most recognizable prop of the physical transformation that turned Miley Stewart into Hannah Montana.
Where Are They Now?
Miley Cyrus: Built a major music career since Hannah Montana, becoming one of the most recognizable former Disney stars in entertainment.
Dylan Sprouse: Continues acting and is involved in business ventures, including co-founding All-Wise Meadery in Brooklyn.
Cole Sprouse: Became well known to a newer audience for playing Jughead Jones on Riverdale (2017-2023), creating a new generation of fans.
Hannah Montana Legacy
The series’ success remains impressive two decades later:
- 14 platinum albums
- 18 gold albums
- 2 hit movies
- Over 500 million hours streamed on Disney+ since launch
New generations continue discovering the show alongside adults revisiting childhood favorites, creating a rare multi-generational audience.
Acknowledgment From Miley Cyrus
Cyrus addressed the anniversary in a statement, acknowledging that Hannah Montana will always be part of who she is, and described the “Hannahversary” as a way of celebrating and thanking fans who have stood by her for 20 years.
This represents notable evolution from earlier periods when Cyrus actively distanced herself from the Hannah Montana character and Disney Channel image.
Fan Reactions
Social media erupted with excitement over the Dylan Sprouse revelation, with fans expressing shock and jealousy over the teenage Disney Channel romance.
The dating confession confirms what many suspected during the shows’ original runs when fans noticed chemistry between the stars at Disney Channel events.
Now Streaming
Hannah Montana 20th Anniversary Special is now available on Disney+.
A variety of merchandise is also available online to celebrate the Hannah Montana anniversary.
The special offers a nostalgic look back at the character and music that shaped many childhoods while providing new insights, like the Dylan Sprouse dating revelation that fans never knew until now.
