28. Tyler Posey
Tyler Posey kissed Miley Cyrus for the very first time. That time he was only 9 years old. Cyrus was Posey’s first ever girlfriend. They met in Toronto while he was shooting the medical drama, Doc with Miley’s father, Billy Ray. “We were so damn young. I would get excited when we would hold hands,” he said to the Daily Mail. They broke up when they were 11.