The 2nd worst thing that happened to an orphan was finding out the milk man passed.
The Milkman
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Explanation
Experiment
Explain Bear
Listen up, buttercup. This joke is funny because being an orphan is already super sad. Then, BAM! You find out the milkman died? That's just kicking someone when they're down. And you, my friend, probably need someone to hold your hand when you cross the street.