'Nice,' he said with a grin. 'Real nice. Still, doesn't beat a '67 Chevy Impala. And Jake's an asshole...ok. I guess, I was taking that a little too far. I meant it in general.'
Questions...crap. It wasn't as if he knew much about Madison. He met her and known her for a few days while working that case, but she had died and he hadn't spent a lot of time with her before. Sam won that with a game or rock, paper, scissors. Dean had the worst habit of picking scissors no matter what, even if Sam always knew that he didn't use anything, but scissors. So in the end, Sam had stayed with the hot chick while Dean trailed the creepy ex.
He watched her go and get her food as he scratched his head and thought over what he could share about Madison. Little brother probably knew more about her than he did. Didn't help him here, especially since he couldn't exactly call Sam about this.
'She's in her mid-twenties, I guess. And she was bitten by her neighbor, who was a werewolf,' he replied awkwardly, clearly not sure how to answer that one.