Milo had a revelation while taking a breather in the hallway with Krista. When Truman put his hand on Milo's shoulder his first emotion he felt was uneasiness, but when doing so Truman squeezed his shoulder in an attempt to intimidate Milo, and when doing so he noticed something about Truman. He was weak. Milo never thought that he'd call someone who used to push him around so easily weak, but that was the only way to describe the grip Milo felt.
This action gave Milo the realization that he really had grown more than what he had expected in comparison to his former classmates. This led him to think of other things from his past involving Truman, and whole doing so, he remembered a moment from when the two were still friends.