Miley Cyrus Reflects on Her “Mistakes” in Life

10. After the series ended in 2011—there was also the 2009 big-screen release Hannah Montana: The Movie in 2009—Miley admitted she struggled to find herself.

“Some of my audience was so attached to a character, which wasn’t me,” she told Howard Stern in 2020. “So, then that does a lot of psychological stuff, where it’s like, ‘Am I valuable as myself?’ OK, the whole show’s premise was that when I had my normal hair and looked like myself, no one gave a s–t about me. And then when I got all dolled up and put a wig on, all of a sudden, you know, I’m being chased by people chasing my tour bus. So, that’s a lot to put on a kid—to go, ‘When you’re yourself, no one gives a f–k.’ But then when they go and kind of groom you to look like something else, something that you’re not, and you’re really young, and it’s a lot of makeup and, you know, wigs and all this stuff, it does something psychologically.”

11. It was love at first sight for Miley when she met her first boyfriend Nick Jonas at a charity event in 2006, when they were both 13 years old. “We became boyfriend and girlfriend the day we met,” Miley revealed to Seventeen in 2008. “He was on a quest to meet me, and he was like, ‘I think you’re beautiful and I really like you.’ And I was like, ‘Oh, my gosh, I like you so much.'” 

After secretly dating, the couple broke up and Miley admitted she “bawled for a month straight” after their split. “Nick and I loved each other,” she told the mag. “We still do, but we were in love with each other. For two years he was basically my 24/7. But it was really hard to keep it from people. We were arguing a lot, and it really wasn’t fun.”

12. Her relationship with Nick inspired her breakup anthem “7 Things,” with Miley even wearing the necklace he gave her in the music video for the 2008 hit. The couple briefly reconnected in 2009, with their short-lived reunion inspiring The Jonas Brothers ballad “Before the Storm,” which featured Miley.