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Demi Lovato's Dating History

E! Logo E! | Slide 1 of 9: Before a certain Disney-fueled entanglement captured the headlines, another famous brother was sliding into Demi's DMs. In 2009, Miley Cyrus' big brother Trace, 20, publicly flirted with a 16-year-old Demi—and vice versa—for two months on Twitter, throwing out tentative plans to see everything from The Twilight Saga: New Moon to the Eiffel Tower together. And that July they did finally spend some real face time together in Los Angeles, even catching a movie (alas, the less romantic Transformers) before Trace left to go on tour. It was all over just days later, though, when Demi tweeted, "Now listen I think you and me have come to the end of our time.. What'd ya want some kind of reaction? Well, okay that's fine." Then it got a little complicated, with Trace posting a pic of his ex Hanna Beth, noting that the snap had been his phone background all along... The Twitterverse's reaction eventually prompted Trace to conclude, "I just got really confused... Is it possible to breakup when you were never together with someone and only friends? Hmm this is new to me." Demi then finished that chapter off for good with a reminder that her album Here We Go Again was dropping in two days. 'Nuff said.

Trace Cyrus

Before a certain Disney-fueled entanglement captured the headlines, another famous brother was sliding into Demi's DMs.

In 2009, Miley Cyrus' big brother Trace, 20, publicly flirted with a 16-year-old Demi—and vice versa—for two months on Twitter, throwing out tentative plans to see everything from The Twilight Saga: New Moon to the Eiffel Tower together. And that July they did finally spend some real face time together in Los Angeles, even catching a movie (alas, the less romantic Transformers) before Trace left to go on tour.

It was all over just days later, though, when Demi tweeted, "Now listen I think you and me have come to the end of our time.. What'd ya want some kind of reaction? Well, okay that's fine." Then it got a little complicated, with Trace posting a pic of his ex Hanna Beth, noting that the snap had been his phone background all along...

The Twitterverse's reaction eventually prompted Trace to conclude, "I just got really confused... Is it possible to breakup when you were never together with someone and only friends? Hmm this is new to me."

Demi then finished that chapter off for good with a reminder that her album Here We Go Again was dropping in two days. 'Nuff said.

© Joe Kohen/Getty Images

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