>>104551520It's his pattern gag.
Setup: Straight-man A says something innocent.
Surprise: Wiseguy B takes offense, or otherwise makes things needlessly awkward.
Punch: Laugh at how awkward A feels now, as A tries desperately to make things better.
Kicker: A only made things worse. Look how awkward they are now. Let's laugh at them.
It's like PC slapstick. I have no idea why he finds this funny, but he does.