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So first off, this happen about 4 or 5 years ago so not really today.
Whenever I would see my friends dad in public I'd always talk to him, because he was just an interesting guy. He ended up telling me one day that he was diagnosed with stage 4 cancer and didn't have much time left.
Well, about a year after that I was talking to that friend and, like I normally would do said "so how's your dad doing? I haven't seen him in a while." I immediately realized what I had done, and after about 10 seconds of silence I made it even worse by saying "I'm guessing it's not well?" Turns out he had died about 6 months before, and needless to say that friend hasn't talked to me since then.
TL;DR: asked a friend how his dad was doing, forgetting that he had died about 6 months ago.
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