1. Tyler Posey

Miley and her first boyfriend met at a time when they were less than 10 years old. Posey stated in the show "Larry King Now" that his first romantic encounters with Miley came about as follows "She tried to make me make a kissy-face. Then she kissed my cheek. "She planted a big kiss on my lips, which I was happy about," he said. "... It was extremely awkward and young ... and adorable and sweet. It was wholesome." Oh, puppy love!