Kid-on-the-square Definition
verb
To be joking, but at the same time really mean it.
Wiktionary
Origin of Kid-on-the-square
Although dating back to the early 20th century, the phrase was popularized by Al Franken in his book Lies and the Lying Liars Who Tell Them when he describes the negative reaction of Paul Wolfowitz to one of his jokes.
From Wiktionary
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