7 Beautiful Women Dylan Sprouse Has (Probably) Dated Throughout the Years

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It’s been a while since we’ve seen the Sprouse twins as those little troublemakers from The Suite Life of Zack and Cody, especially considering that it’s been FOUR years since Dylan Sprouse‘s nude pics leaked on the Internet. While no one wants their personal photos to illegally surface online in a cruel invasion of privacy (the actor, at least, had a good sense of humor about it), there is something about a scandal that helps the world say, “Oh, they’re definitely not just a Disney kid anymore.”

During his transition from goofball tween to handsome young adult, the 24-year-old definitely tested the waters of dating while famous. Like his brother Cole, Dylan has been in relationships with both famous and non-famous beauties, proving we all have a chance to date a celebrity. But enough about us — here are all the ladies that made their way into DS’ heart over the years.


Miley Cyrus

Over 10 years ago (feeling old, yet?), Miley and Dylan dated for ONE day! The Suite Life star confirmed the rumors on Jimmy Kimmel saying, "We met on her set, I believe, and we dated. And then Nick Jonas walked by and it was over!" LOL. Yep, that seems to be the way relationships go at 11 years old!

Photo: Twitter

Becky Rosso

Even though Dyl's twin was rumored to be dating both of the Rosso twins, he was romantically linked to Becky after she appeared on The Suite Life on Deck in 2007.

Photo: Disney Channel

Daveigh Chase

Daviegh played the voice of Lilo on Lilo & Stitch: The Series, which is how she and Dylan met each other! According to rumors, their relaysh was really just a fling and things were over almost as quickly as they began!

Photo: Instagram

Danielle Glasscock

After some blurry photos surfaced of Dylan on a date with a "mystery girl" (they were sitting on the same side of the booth laughing, and at one point she even cutely fed him a french fry!), fans scrambled to find out who she might be.

Eventually, people discovered that the girl in the photo was Victoria Justice's BFF, Danielle! While they made a pretty cute first-date couple, the pair was never seen out together again.

Photo: Instagram

Kara Crane

Kara was a guest star on an episode of Suite Life and it looked like her on-screen chemistry with Dylan transferred off camera. They dated for a few months when the Disney guy was 17, but then things fizzled.

Photo: Getty Images

Brenda Song

Brenda and Dylan were strictly BFFs during their time on The Suite Life, but in 2010, sources said that the duo was beginning to see each another "in a new light." They were spotted hanging out, strolling arm-in-arm in Vancouver, which obv had everyone thinking they were a couple.

Photo: Getty Images

Dayna Frazer

Dylan and Dayna got together in 2013 and have been going strong ever since. While rumors circulated that the two had briefly broken up in 2016, they set the record straight by posting more shots on social media together. They became official in February of 2014, so it looks like they're just about to celebrate their 3-year anniversary! Congrats, cuties!

Photo: Instagram

All the Girls Cole Sprouse Dated Before He Got Hot

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