Topperism Intervention Possibly Needed

Internet Hive Mind, gather 'round.

I worry, sometimes -- because it's a hobby of mine -- that I come off like "Topper" in the Dilbert comic strips.

Question: Where is the line that should not be crossed when you're riffing on someone's Facebook joke, sharing a story similar to the one in the main post (or even in a comment). Where do sympathy/empathy and Topperism intersect?

If I DO come off like Topper more often than not, would SOMEONE please tell me so I can get into a program or intervention. It's been weighing on my mind.

And why is it so funny when Topper meets Loud Howard?