The context of the following conversation is Ash wanted to know what Jesse had been doing so he elicited a response from Jesse.:
Ash says I think Jesse thought I was being too nosy the other day..
The friend responds Why, where you questioning him or something?.
Ash responds A little. I saw him take something out of a coat pocket on the coat rack at school and asked what he was doing..
The friend responds Well, was it his coat?.
Ash responds I didn't think it was. Turns out it WAS his coat.  It was different from the one I recognized because he had just bought it..
The friend responds Oh. I get it. Oops. Well at least he knows you look out for people. How would you know he'd just bought a new coat?.