no, he didn't look cool. He looked like a child throwing a tantrum when he doesn't get what he wants
Nah, she just wanted him to be honest for once. She's not into the whole "cool silent type" because to her, it's bullshit. People obviously still have feelings, so to her, acting like they don't is lame.
Think about it. She likes the guy who can't hide how he actually feels and thinks. And she herself is the kind of person that just says what she thinks. That's why Okada became friends with her in the first place, her thoughts usually matched her words.
To her, cool is putting everything out there. Both times he's seen her smile like that at him, was when let his feelings show.