When he said "you're prettier when you smile", I thought it might stir some people up. For me reading this, he is watching her grow and he cares for Ebony so saying that meant that it's fine for her to smile and laugh as she wants.
But in context of modern times, if some guy that don't know me well enough said the same thing, I wouldn't feel the same way. I would feel offended, in fact.
Other than that, I think it's right for him to want her to grow and get more experience before falling in love. I am willing to wait for that development.