1. Tyler Posey

Miley and her first boyfriend got acquainted at a time when they were less than 10 years old. Posey admitted her show "Larry King Now" that Miley's first romantic encounters were like this: "She tried to make me kiss me." She then kissed my cheek. "She gave me a huge kiss right on my lips, and I loved it," he said. "... "... Oh the puppy loves!