Posey recollected how Cyrus had planted a big kiss on his mouth back then, which he thought was “very awkward, and very young ... and cute, and sweet, and wholesome.”
Dylan Sprouse, who dated Cyrus before she left him for Nick Jonas, spoke about the ordeal on "Jimmy Kimmel Live!" saying, "We dated. And then Nick Jonas walked by and it was over."
Jonas eventually broke up with Cyrus and said that he was "kind of flattered" when the pop star wrote "7 Things" to take a dig at his relationship with Selena Gomez.
Justin Gaston dated 16-year-old Cyrus for nine months before she started getting friendly with ex-boyfriend Nick Jonas again, which led to some angsty breakup tweets at the time.
In one of his posts after the split, Gaston quoted John Mayer's famous heartbreak tune, "Dreaming with a Broken Heart," writing, "Do I have to fall asleep with roses in my hands?"
The Australian actor eventually announced the split on Instagram, writing, "Miley and I have recently separated and I wish her nothing but health and happiness going forward."
While Cyrus met Nickelodeon actor Avan Jogia when she was 18 and fresh on a break from Liam Hemsworth, the rumored romance between the two fizzled out about as quickly as it began.
However, Jogia had only good things to say about the pop star during his conversation with TigerBeat TV where he called her "super cool ... like a sweet down-to-earth [girl]."