Wyll's banter has some serious timing issues. I got the rat comment shortly after we had our run in with Gandrel and he suggested Gale could pick up a new monicker "Master of the Weave" basically two steps after Gale confessed his whole story. I am sure it wasn't intended this way, but the timing made it feel cruel. The exchange he has with Lae'zel about whether she has ever done a good deed also feels like he is making fun of her, because she doesn't understand the concept.
Wyll tries to make friends, and maybe he would get better at it if the writing allowed him any kind of character development.
For me the banter always triggers the moment I teleport somewhere. So every time it goes like this: I grab Wyll from camp, leave camp, I'm still in a loading screen, and I hear SO ASTARION, HOW'S THE. At this point it just makes me laugh.
The banter is a mess. Sometimes it recognizes what you did in the game, like different versions of SH asking Astarion about sweethearts. Sometimes, like yesterday, you'll have Astarion ask Wyll if he's heard of Cazador hours after you've already dealt with Cazador.