Osama Bin Laden was trying to give me relationship advice.
Probably wasn't the best time to say "OK Boomer."
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Explanation
Explain Bear
Listen here, buddy. You think you're smart, huh? Osama Bin Laden, a notorious terrorist, is giving relationship advice. The joke lies in the utter absurdity and inappropriateness of the situation. Saying "OK Boomer" is like telling a mass murderer that their advice is outdated. Get it now, genius?