The fact that there were 'nerd Bards' and the fact that she seemingly refused to use the word musician told Raylan a little. So it was a D&D thing. Shit he coulda used Tim right now. His head tilted a little at the question of his age - No, he wasn't going to tell her but his age had little to do with it.

Harlan however..

"A gift.. So you're.. Talented. Great, glad we cleared that up," he said as he started walking again. "What's the DGA then?"

Maybe he'd get a more sensical answer with that.