Theon + Smiling = Strength
Theon smiles a lot:
No doubt he was smiling. He smiled a lot, as if the world were a secret joke that only he was clever enough to understand.
He was smiling. Ever smiling.
She studied Theon Greyjoy’s sly smile, wondering what it meant. That young man had a way of looking as though he knew some secret jest that only he was privy to.
A callow youth, always smiling, skilled with a bow.
[…] he had declared, smiling that way he did
And Theon, if he lived, was just as hopeless, a boy of sulks and smiles.
Theon smiled a lot, its one of the things observant Tyrion notices about him, but then comes the question; why is he so damn happy all the time?
By all rights, Theon should be a really depressed teenager/young adult. He was stripped of his home and family at age nine and forced to live with a man who appears cold, who would chop off his head if his father stepped out of line (don’t forget the fact that his brothers died and his sister got to stay home with their family).
Personally, I think Theon smiled so much as a sort of ‘fuck you’ to the world. Like, you might have it bad but I did too and I’m still smiling. Almost like it makes him stronger than everyone else and like he is clever (“as if the world were a secret joke that only he was clever enough to understand” - AGOT, Bran I).
Of course most people just find it annoying (“That young man had a way of looking as though he knew some secret jest that only he was privy to” - ACOK, Catelyn I) which on a way is understandable, Theon was always quite “cocky” and “sly” too. But it’s almost like they find his strength annoying, because despite everything that has happened to him - including being beaten at Winterfell
and Ned Stark not being that ‘perfect father’ to him that most of the fandom sees him as - he was still smiling that wide, annoying smile.
And then Ramsay knocks out his teeth (along with much worse) and said that whole, “I may have broken some of his pretty white teeth.” like the
cunt bad guy he is. And so in a way, metaphorically I suppose, Ramsay also broke that strength and cleverness, because Theon’s smile represented them both.
TLDR; I think his smiling is a very important part to Theon which is mostly overlooked as cockiness and him being an ass.