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Wasn't it good that he kept talking though? Sorry for being crass, but I'd prefer him loosing this case.

Agreed.

But that's a weird thing to do. Why advise people to do stuff detrimental to the world?

Trying to help people be better versions of themselves is a good thing.

But this wasn't about trying to help someone to be better, it was to help them avoid facing consequences for being bad, like advising a wife beater about concealer options for his wife (overly dramatic example, I know).

"You should stop doing dumb/illegal stuff, it might impact you" is very different advice than "You should stop talking about the dumb/illegal stuff you do, they may stop you".

It was probably an error in judgement for me to have advised the man to stop talking.

Or judgment even

Both spellings are considered correct, although i personally prefer 'judgment'.

Tell me you are from the U.S. without telling me you are from the U.S..

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