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We wrote some songs and just played a lot of music. The relationship didn’t last and, when it ended, the two of them bombarded Twitter with their sadness. They didn’t go public with their relationship until 2005, a year after they first began dating The relationship lasted for three years with Duff being the one to end things.

“Tears are words the heart can’t express,” Cyrus wrote. Apparently the age difference was causing problems.

4 Kobe and Vanessa Bryant met in 1999 when she was working as a backup dancer for a music video for Tha Eastsidaz.

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I want to be with somebody who is more worldly than me, somebody who can give me guidance and is completely secure and comfortable with who they are.” 6 John Mayer started dating Taylor Swift when she was only 19.

9 Prince met Mayte Garcia when she was 16 years old and he was 31.

It was backstage at one of his concerts in Barcelona and he was immediately taken by her and said, “There’s my future wife.” A romance didn’t begin immediately, however.

2 Doug Hutchison was 51-years-old when he married 16-year-old Courtney Stodden.

She allegedly needed parental permission to tie the knot with her older lover, but that didn’t stop him from embarking on their controversial relationship.

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