Well, come on. He wouldn't be Dean Winchester if he didn't at least give it a shot. She was a fantastic looking woman, sitting alone, he was willing to risk the rejection for even the chance of it.

"Yeah, and we see those videos all the time on Youtube," he snorts, "Or like the time Sammy had a case of bad luck and set his arm on fire. That was pretty awesome."

Except for Sam getting shot later by Bela, but she was a stinging sensation he didn't like thinking about too much. It's much better to think about how hilariously horrible it had gone for Sam after he lost the rabbit foot.