From the definition of pointed, we know that "pointed question" is something like: "A "sharp", piercing, or directed question".
And "pointed question" has been in English since, roughly, the American Revolution:
However, there is no dictionary entry for the phrase "pointed question" that I could find, neither online nor in my print dictionaries.
But I remember an old teacher saying that the phrase originated with adversarial questioning where literal knives were used to "persuade" the questionee. Is there any chance that's true?
Both "pointed" and "question" have been in English for over 700 years. What's the story of how they first came together roughly 250 years ago?
Best Answer
The earliest appearance of 'pointed question' I found was this from a 1777 US pubication:
The sense of 'pointed' corresponds to OED sense 5b of "pointed, adj.",
As remarked in OED, however, sense 5b is "[s]ometimes difficult to distinguish from sense 5d". Sense 5d is
It was perhaps later, through a conflation of the meaning with the very similar 'home question', that the meaning of 'pointed' in 'pointed question' veered toward 5d. That latter sense is attested first from 1768, in Sterne's Sentimental Journey:
The variant, 'home question' is first attested from 1687, with this sense:
Returning to sense 5b: it is first attested from the late 17th century. It was then that the sense was bloody, as might be expected from the meaning of "penetrating, acute, incisive; piercing, trenchant, stinging". The second quote in OED that attests this sense is from Daniel Defoe's The true-born Englishman; a satyr, published in 1700:
The two figurative senses, 5b and 5d, remain entangled in the contemporary meaning of 'pointed question', but the earlier sense 5b informs more directly the violence of the sense inherited by 'pointed question' from literary use of 'pointed Truth'.