I’d say by training on a lot of contextual situation: what is person thinking pairs. It’s stuff that will be grossly underrepresented in content simply because it is “obvious “ and normally not mentioned. That would probably be enough to bring audience awareness into the worldstate of the token-space.

In theory, could you teach an LLM to simulate "humor" through pattern memorization?

I suppose to come up with an original joke you need to yourself be able to find something to be funny.

I don't know. Humor is a very high dimensional space in itself and different to each individual. I would be surprised if any LLM could be trained to be a consistently well reviewed comedian. "Humor" is just such a nebulous metric.