To be joking, but at the same time really mean it.
Origin
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 (2003) where he described the negative reaction of Paul Wolfowitz to one of his jokes. Additionally, in 1983 jazz singer Mose Allison wrote and performed a song called "Kidding on the Square" on his album Middle Class White Boy; in the liner notes, he described it as "joking with serious intent."
Modern English dictionary
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