I'm gonna be (maybe too) charitable to Chappelle here.
Chappelle has "uninterested celebrity who feels obligated when someone asks to take a pic" face, so I'm gonna say its possible Boebert just happened to run into him at some event and asked for a picture. This is on Boebert's twitter, not Chappelle's, and Boebert is gonna be an inflammatory basically-a-nazi and throw in some pointless trans hate because that's the only thing she's got.
EDIT: The other woman is apparently another right-wing nutcase, so maybe I'm wrong. But Dave doesn't really look like he's comfortable to be there.