[He might be full of himself, but there's no way he's not going to pick up on a girl giving him the once over.]
Well, when you like fixing cars in your free time, it comes in handy. [See! Dean's an awesome catch, so catch him.]
I do. Sam, about four years younger then although he's a bit of a freeloader at the moment, not that I can blame him. He just went through a nasty break-up with his girlfriend. [What the hell Sam had seen in Ruby, Dean still didn't know.]
What about you? You have any siblings? [And he's just going to nonchalantly take a sip of that coffee. After her warnings, he wanted to be prepared for the worst.]