To me it usually means someone's humour isn't mainstream, and that mostly others have a hard time understanding or relating to it. Or perhaps they're really into specific subjects like sci-fi or sports, so unless people know it they won't understand the jokes.
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No. Probably means they don’t know how to accept, visualize, think the humor. Maybe it’s not widely accepted or popularly funny.
It's just their style of joking. They might have a dark or dry sense of humor and that isn't for everyone, so some might not see the humor in it. It doesn't mean that they think that you're stupid.
Probably... that's the way I would hear a comment like that. Because "weird" has a negative connotation to it.
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