It’s been a while since we’ve seen the Sprouse Twins as those little troublemakers from The Suite Life of Zack and Cody. Cole Sprouse is currently slaying it on Riverdale while dating co-star Lili Reinhart. But where has his brother, Dylan Sprouse, been?

Unlike Cole, Dylan hasn’t done too much acting over the years, choosing for his life to be a little more private. But recently, he’s been making more of an appearance on the scene! During his transition from goofball tween to handsome young adult, the 25-year-old child star definitely tested the waters of dating while famous. Like 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 Cyrus 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!

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.

Daveigh Chase

Daviegh Chase played the voice of Lilo on Lilo & Stitch: The Series (and in the movie), 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.

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 Glasscock! While they made a pretty cute first-date couple, the two were never seen out together again.

Kara Crane

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Kara Crane was a guest star on an episode of The 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.

Brenda Song

Brenda Song and Dylan were strictly BFFs during their time on The Suite Life, but in 2010, reports claimed that the duo began to see each another “in a new light.” They were spotted hanging out, strolling arm-in-arm in Vancouver, which obvi had everyone thinking they were a couple.

Dayna Frazer

Dylan and Dayna Frazer got together in 2013 and dated for quite a bit of time. In August of 2017, however, allegations broke that Dylan cheated on Dayna (she even posted about it on her Instagram Stories!). He totally denied the rumors, but still, the couple broke up and ended it there.

Barbara Palvin

After Dylan and Dayna broke up, we didn’t hear too much about his dating life for a while. In fact, he kind of fell of the grid for a bit. So you can imagine how shook we were when we saw that he might be dating model Barbara Palvin! The two traveled to Russia together for the World Cup and took a bunch of cute photos. We don’t have confirmation yet, but it looks like this may be the real deal!

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