When people use the term uncomfortable conversations do they really mean one way lectures or real conversations? I just hear people like Bernstein using this term a lot and I really wonder if they mean a true conversation.

They mean you're about to start watching the UK version of The Office.

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coversation = dictation in newspeak.

Thought it meant you’d be sitting in back of a Volkswagen bug.

Right leaning black guys are called Toms. Is that having an honest conversation?

No.

Is it when 2 people face each other on stools and one is forced to read from a script and feel shamed for something they never originally said or wrote in order to make the other person cry?

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My Maserati does 186.

"Just read it!!"

Race relations would probably not rate in the top 10 of my most uncomfortable conversation topics

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O judgment! Thou art fled to brutish beasts,
And men have lost their reason.

Nice Mallrats reference Very underrated movie imo.

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Mr. Trump is unfit for our nation’s highest office.- JD Vance
When a clown moves into a palace, he doesn't become a king. The palace turns into a circus. - Turkish Proverb

Yep... no way I’m creative enough to come up with that in my own

And yeah, it’s an entertaining flick.

It means he's about to drop a liberal bomb on you. Of course, he's not interested in any real conversation. He wants to lecture you, tell you you're a racist if you don't agree with him, etc.