Sora asks these questions because he's curious about other people! If he has to have two adolescences worth of relationships and conversations in him, he has to learn something from it all. This is what he chose to come away with: Listening always helps. And it goes both ways!

"A leader, huh... Sounds like I need a guy like you." He drops the peel, puts a hand to his cheek and rests against the table. Not really implying anything! Just a simple statement of fact. "And that's why you talk so officially. You've been a leader, so you have to make decisions for yourself and other people without help. That makes sense. Sounds lonely, though."