It sounds like, especially in those early years, Emily Osment and Miley Cyrus had a complicated relationship. In a 2008 Seventeen interview, Cyrus said the two became “really, really close” immediately and compared Osment to a more responsible “older sister.” More recently, while appearing on an October episode of the “Chicks in the Office” podcast, Osment alluded to early social outings before “Hannah Montana” blew up. She said, “Miley used to come with me to my school dances and nobody would know who she was and immediately everything changed and that was very strange.”
But in “Miles to Go,” the autobiography Cyrus published in 2009 (via Goodreads), she said that the two struggled to get along during the first two seasons of the show. She noted that she was intimidated by Osment’s prior acting experience, and the co-stars didn’t always agree. Cyrus also called Osment “reserved” but also said Osment was “beautiful and athletic” in the book (as reported by Insider). She wrote, “There was competition between us — girls struggle with that, and we were no exception. I didn’t do much to fix it. I mean, I wanted to, but I had no idea how to go about fixing it. I never got along with girls as well as I did with guys.”
She also said the two “tried to be friends, we really did, but it always ended in a fight.” In fact, these fights were witnessed by the cast and crew, and once their families had to step in. Still, something changed between them after the third season. “I think somewhere in the course of trying to keep the peace and act like friends, it sort of became true. It felt natural,” Cyrus said.