"Maybe he realized no matter how much he cries, no one will be coming to save him" These words have been stuck to my head when I've read them, that he must have gone through rough and tough circumstances in his tweenage or teen years where he ever wanted to be free or rescue or guided like a normal child, (I've strong feeling he has no normal childhood as well as teen years and so on.)
Added more...MJ's Childhood song suit him.
I have to say, I felt the same way when I read it. It's this little (maybe even not so little) hint that there is perhaps a backstory there. And the nice thing is, sensei may decide to tell us the story one day, but in all likelyhood, she won't - and that's perfectly fine. Because I feel that these are the little bread crumbs she throws us from time to time that we as fans can pick them up and get our imagination going. In a way, that is what you have already started doing: You imagine what his offhand remark actually might mean and what the story is behind it. That is good storytelling: Give the reader something that interests him, sparks his curiosity and gets his fantasy going. And of course, it addsa another layer to the character and the enigma that is Asami. And doing so without actually telling us the potential backstory? When you come to think about it, that's pretty cool. :)
We always agree with each other, Lady. :) It's fate! <3

http://www.mangago.me/read-manga/you_re_my_loveprize_in_viewfinder/mh/v08/c053.8/8/
Is this a hint to asamis past? ╥﹏╥