Problem using ironic humor

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Ken Kesey used to say "He outsmarted himself."

Absolutely! I have made absurd comments for effect and they take it literally. Then you realise how they perceive you to be, and it doesn't match how you perceive yourself!!

Happens a lot. I used to try and explain my stance and how the joke does not reflect my actual opinions but sometimes it's more fun just to go along with it. Those that see the humor enjoy it, others probably aren't worth the time anyway.

This happens to me a lot, and it is very frustrating at times. Some people seem to be able to use irony and get away with it, and nobody finds it necessary to explain patiently to them that they have misunderstood, etc., etc. And yet when I use irony, there is almost always some tiresome person who seemingly thinks that I am a complete idiot who doesn't realise that entrepreneur is a French word, or whatever. The worst is when I use irony in "real time" in a social setting, and some wretched person interrupts during the middle of what I am saying in order to educate me on what I have "misunderstood."

I've concluded that probably this relates to the fact that I tend to speak in a very deadpan way, and they somehow decide that I must be always believing everything that I am saying. It can be a real bummer when trying to tell a joke, though!

Exactly.

This is what happens to me. Luckily, I have been working with the same project team for 4 years and by now they seem to get me, although sometimes I will seek reassurance by apologizing for something I said that could have been out of line, at which they always tell me that they "love me". Which is one reason I am hesitant about fully retiring when I turn 70 this year. BTW this is now a 100% virtual environment I work in now, which can sometimes cause anxiety.