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TIL when 42-year-old Hugh Hefner asked 18-year-old Barbi Benton on a date she said “I don’t know, I’ve never dated anyone over 24 before.” To which Hefner replied, “That’s all right, neither have I.”

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6EQ5Z TIL of Russia's "Dead Hand" (aka "Perimeter") automated nuclear defense system. If a large spike in radiation levels was picked up within Russian borders (indicating nuclear detonation), the system would target many different cities and launch nukes. It is believed to still be active.
5BLp TIL in 2009 Amazon sold diapers at a 100m loss to scare Diapers.com into selling them their business or face being ran into the ground
9YQaQ TIL: There is a hotel in Minehead, UK called the Foxes Hotel that has an all disability staff and teaches them skills of trade for them to use when they get jobs in the real world.
RvA8 TIL that Timothy Dexter the 18th century American businessman, writer, and noted eccentric, faked his own death to see how people would react. About 3,000 people attended Dexter’s mock wake. Dexter did not see his wife cry, and after he revealed the hoax, he caned her for not grieving enough.
k0d TIL that Adolf Hitler wrote a letter from jail begging a Mercedez-Benz dealership for a car loan. The letter was found at a flea market.