I know we all wished that Orpheus didn't look back, but do you all realize how unrealistic that would have been. He's a character that doubts himself constantly, the only time he is sure about something is A) when he is writing his song and B) at the end of all I've ever known when he promises eurydice that they will be together forever. He starts to gain more confidence in If It's True, but a character can't change all of a sudden like that and leave his old ways behind. When Orpheus turns it shows that he still isn't confident, just because he was for a bit doesn't mean that now he is always confident. Just because we were something once doesn't mean that we need to stop working on ourselves, if we do it only once we eventually fall back into our old ways.