My throw-away title for this post turns out to be a question Donald Casadonte has given a lot of thought:
There are really two questions that one could ask: at what did Jesus laugh, and did Jesus ever cause anyone else to laugh. To answer the second question, first (and the topic of your blog), for instance, in the exchange with the Sadducees on the subject of marriage...
Why did Jesus not gently mock his accusers? The probable reason was the context. Jesus had the perfection of virtues and, as such, would not have mocked his accusers because it would have been imprudent in the context. It would have made the crowds laugh, but it would have infuriated the people he was trying to correct. Thus, on the matter of Jesus making jokes, he could have made them, but his range would have been more restricted than ours because his vision was unlimited (at least in his divinity)...
There are different classes of possible worlds: physically possible worlds, logically possible worlds, morally possible worlds, semantically possible worlds, etc. Because of Jesus's divinity, he is able to access certain worlds which to us are only possible. For instance, we can imagine a possible world where we can walk on water, but Jesus can realize such a world.
Thus, the class of jokes where walking on water is the imaginary world would be non-accessible for Jesus, because to him, it would be an realizable world...
In fact, because Jesus can do anything which does not violate his divine attributes, he has access to a restricted number of possible worlds, and thus, his joke set is much smaller than mere mortals. He can, however, access some.
Which? Well, possible worlds depend on the imagination and imagination lends itself to the formation of metaphors and Jesus did use metaphors in the form of parables. This gives us a clues as to his set of possible worlds and how closely they match our range of possible worlds. Thus, a possible world where men's souls are like wheat (as in weeds among the wheat) could be an imaginary world which Jesus could use to form a joke. He could also make jokes from possible worlds which, to us, would be imaginary, but not to him. In that case, what we would perceive as a joke, he would see as a truth revealed by a subsidiary truth.
Jesus, as we are, would be restricted from accessing possible world where the moral virtues are not as they are in this universe. He could consider such universes, but he could not hold them as contingent and possible with this universe, because then he would have to imagine the case where he, as a Unitary God, would contradict himself in his divinity and *this* application of the Law of Non-contradiction, cannot be projected out In other words, Jesus could not make jokes about God being both just and unjust. He could not make jokes involving pornography (imprudence prevents this). Mere mortals can make sinful jokes which access immoral possible worlds (although we should not). Jesus cannot do this because he cannot sin. Thus, although we are restricted to certain morally "clean" possible worlds, but can violate this restriction, Jesus cannot and thus, he is more restricted than we are in terms of morally accessible worlds.
As for logic or semantics, Jesus has full access to all logically/ semantically possible worlds where they do not violate the restrictions from the physical or moral possible worlds. We see, in fact, a prime candidate for a joke in the saying: "Come with me and I will make you fishers of men". This would be classified as a mild semantic joke.
Does Jesus respect jokes? The non-sinful ones would, I suspect, be appreciated where the possible worlds could be accessed. Walking on water jokes would be truth statements, not incongruities for Jesus, but the statement of the Syrophoenician woman about, "Even the dogs eat the scraps that fall from the Master's table," impressed Jesus so much as a type of desperate play on words (if I may use the term, although the woman was not in a playful mood), that he said: "For making that response, go home, the demon has left your daughter." Why did it impress Jesus, beyond being a play on words? It is because the woman was willing to accept the impossible world where she could be reduced to a dog and still ask for a dog's rights. She treated Jesus as if she were the dog and he were her master. It was a profound statement of faith. Humor depends on the switching between a real world and an imaginary possible world which isn't right in the original context, but cannot be dismissed.