Her really should, but you can't really blame him for /not/ smiling. He's basically an outcast in the group throughout the entire game while everybody else has somebody, so you know, that's not really anything to smile about. ;; I think he smiles twice in-game, but it's kinda hard to catch.
I can agree with that and definitely don't blame you. He screwed up, /big time/, but hey, he really was trying. And I love him for that, even though his attempts at helping all went horribly wrong. ;3;