1. Tyler Posey

Miley and her boyfriend met when they were both younger than 10 years. Posey stated in the show "Larry King Now" that his first romantic moments with Miley were as follows "She was trying to get me to make a kissy-face. Then she kissed my cheek. "She planted a big kiss on my lips and I enjoyed it," he said. "... "... Oh, the puppy loved!