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Miley Stewart, portrayed by Miley Cyrus, was just an ordinary girl. She had boy problems just like the rest of her high school friends. Here’s what we know about this Hannah Montana character and some of her old boyfriends. 

'Hannah Montana' episode titled 'I'll Always Remember You'
‘Hannah Montana’ episode titled ‘I’ll Always Remember You’ | Eric McCandless/Disney Channel via Getty Images

Miley Cyrus portrayed Miley Stewart for several episodes of the Disney Channel original series, ‘Hannah Montana’

She had the best of both worlds. This Disney Channel character went from just a regular teenager to an international pop sensation, thanks to her Hannah Montana persona. 

Disney’s television network created several episodes of their original series, most featuring Cyrus as the main character. Several other actors appeared as Miley’s friends and her ex-boyfriends (even if the relationships didn’t always end well.)

Miley Stewart dated boys like Derek, Jesse, and Jake Ryan

She was an international pop sensation, but Miley Stewart also had some boy problems. For a brief time, Corbin Bleu portrayed Johnny Collins, a character who proudly used ketchup as a moisturizer at the recommendation of Miley Stewart. 

It turned out that Johnny had a huge crush on Hannah Montana and won a date with her during the “We’re All on This Date Together” episode. Thanks to Rico’s intervention, it didn’t work out. 

For another episode, Austin Butler played Derek, a super cute guy who was set up on a movie date with Miley Stewart. Unfortunately, he was very scared of horror movies and ruined the entire night. 

When Miley wished to be Hannah Montana all the time, she was pleasantly surprised to find out she was dating the actual musician named Jesse McCartney. Of course, this was just a fantasy, and as soon as Hannah went back to being Miley, McCartney stopped being her “man.”

For The Hannah Montana Movie, Miley Stewart had a fling with a local cowboy named Travis Brody (Lucas Till.) They shared a close friendship and even fixed a barn together. However, this relationship did not extend beyond the movie, presumably because Miley lived in California. 


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Perhaps her most serious relationships were with rocker heartthrob Jesse and the zombie slayer Jake Ryan. Miley had the difficult decision of choosing between the two boys during the “He Could Be the One” episode of season 3. After that, Miley continued her relationship with Jake Ryan.

However, after learning that Jake cheated in “It’s the End of the Jake As We Know It,” Miley broke up with her high school sweetheart. In the season 4 episode, “Been Here All Along,” Jesse asked Miley out again, and she happily accepted. 

Disney Channel’s original movie, Hannah Montana: The Movie, as well as the complete seasons of Hannah Montana, are available on Disney’s streaming platform, Disney+. Additionally, the Nicholas Sparks movie featuring Miley Cyrus, The Last Song, is available for binge-watching on this subscription service.