I know it's his AS, but it still gets on my nerves

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Perhaps it's the WAY he said it though. If he said it in a leering/crude way, I could see how somebody would be offended. Just like some guy at a parking lot looked at me and said "Hey sweetheart." It wasn't the words, since if he was like a friend of something and said in a not sexual/creepy way it wouldn't be bad. But he was like 40, I was 15-16 at the time, and he was really creepy. So yeah, I was offended and scared.

I can't believe you didn't have a comeback for that. Especially since you find him so annoying. Like "I'm sure they'll appreciate that." Don't get so offended just have fun with it but be gentle.

I believe I might understand your frustration with his attempt at a joke. There's quite a difference between successfully telling a joke that's appropriate for a situation, or telling one out of mimicry simply because you've observed other people tell it successfully. In the latter scenario, there seems to be no sincere weight or cleverness behind the joke; rather a shallow repetition.

As none of us were there to hear his delivery, I'm only making an assumption. I commented as such because I work with another man who has been diagnosed with Asperger's Syndrome, and while I refrain from participating in any and all humorous banter, he does not. He goes to great lengths to repeat jokes that he feels might be appropriate, but they only yield stares or awkward laughter. It casts a light of annoyance on him and he's regularly avoided.

Is this in the same realm as what you've observed with your acquaintance?

I do not know the context but that sounds like something I would say depending on the circumstances. I have said similar things here in this forum in jest. That guy made of been uncomfortable & made a poor attempt at humor to relive tension