He stops when she stops, eyes fixed on her, trying to read this reaction; but while that reaction is... gooood...? and arguably progress — it still gives him rather little to go off. He's never had to restart an interaction before, oh god, why did he phrase it like that, now he's trapped by his own joke. He fumbles, glancing aside like he'll find some stray bit of wisdom lying around, which of course he does not. So after an awkward beat, he just offers her a sheepish smile, trying to lighten the mood in spite of himself, making jokes at his own expense now instead. Well— that's the implication, in his eyes; without the 'grew up isolated from society' context, the joke seems less self-effacing than he means it to... just seems cheeky (which, in fairness, it also is).

"Alright, sooo... Hello. How're you today?"

He lays on an extra layer of charm in his inflection, pulling his best 'people person' voice out, as if he's impersonating a... normal, calm, polite person. So the shift back to his own more typical, genuine airs is a bit stark, even as he's trying to use his best real people skills to get her to smile or chuckle or something.

"Well? How was that? Better, yeah?"

He grins at her expectantly, holding up two thumbs up and nodding at her eagerly, as if begging for her critique. Riiiight back into the jokes... This is how to make friends, right? By trying to entertain them until they concede to liking you? Yeah, sounds right. That's what's done the trick in the past. Sort of. Besides sneaking up on them pretending to be a murderer, since that trick's apparently out...