Article: Good Questions: Partridge in a fair plea

SINCE when has it been possible to bore the pants off someone? (Tim Paine, Bristol)

Since the late 1940s, according to Eric Partridge's A Dictionary of Slang and Unconventional English, although you could bore someone by wearying them as far back as 1768. The earliest citation of pant-boring in the OED comes from P G Wodehouse's Jeeves and the Feudal Spirit (1954): "They were creeps of the first water and would bore the pants off me." For a higher class of boring, we refer to Malcolm Muggeridge's description of Sir Anthony Eden: "He was not only a bore; he bored for England."

Why are nave people wet behind the ears? (Mollie Caird, Oxford)

According to Everyman's Modern Phrase and Fable, it ...

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