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It's a thin line between witty and flippant

Kit is developing a great sense of humor. He likes to tell jokes, makes some up, and tries to sharpen his wit exchanging funny barbs with me. Unfortunately, not everyone is so fond of his banter. In fact, sometimes he doesn't know the difference between funny and backtalking, or just sarcasm, to an adult.

I have tried to explain that what sounds like a joke in his head might come across as insulting to the person he's talking to. I think he understands it but it's a subtle point. For a while he figured he could just start with the phrase "Nothing personal but..." like it's a disclaimer and then pound away with a jab. It's impossible to give real examples because they are too context dependant but it might go something like this: "Nothing personal but those glasses make you look like a fish." Ha, bloody, ha.

Neither Tish or Buddy get him in quite the same way I do, so while I let most of it roll off, it pushes their buttons in a hurry (A response, alas, that he doesn't mind cultivating -remember that Kit is a drama queen). The comment above notwithstanding, some of his wit is really quite funny and quick off the mark. But I can understand getting pissed off if you're looking for a kid to get ready for school and you get a smart aleck remark instead.

I've been trying to coach him to take a second to think about whether the comment is appropriate, both in timing and in content, before it pops out his mouth. I want to encourage his sense of humor, but it's a thin line between rapier wit and cutting insult.