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:

nGram of "pointed question", case insensitive

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?

  • Imagine that your interrogator is holding a sabre to your throat. – Hot Licks May 16 '17 at 11:04

The earliest appearance of 'pointed question' I found was this from a 1777 US pubication:

To balance a judgement made in moments of superiority and pride, let me begin by a pointed question: should America now, for the first time, be raised out of the deep....

The Remembrancer, or impartial repository of public events

The sense of 'pointed' corresponds to OED sense 5b of "pointed, adj.",

Penetrating, acute, incisive; piercing, trenchant, stinging, etc.

As remarked in OED, however, sense 5b is "[s]ometimes difficult to distinguish from sense 5d". Sense 5d is

Marked, emphasized. Of attention, thought, criticism, etc.: directed unambiguously towards a particular person, subject, etc.; clearly making a point.

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:

A course of small, quiet attentions, not so pointed as to alarm—nor so vague as to be misunderstood.

OED collection.

The variant, 'home question' is first attested from 1687, with this sense:

home question n. now rare a direct or pointed question, esp. one of a personal nature....

1687 R. L'Estrange Brief Hist. Times I. ii. x. 229 Now This was a very short Answer, to a Home Question.

op. cit.

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:

Search, Satyr, search, a deep Incision make;
The Poyson's strong, the Antidote's too weak.
'Tis pointed Truth must manage this Dispute,
And down-right English English-men confute.

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'.

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    Interesting research, as usual, but the real question here is about OP's teacher folks etymology. – user66974 May 16 '17 at 8:57
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    @Josh, the evidence presented suggests no literal daggers or swords were involved in the "coming together" of 'pointed' and 'question' in 1777 (or earlier), merely two figurative senses of 'pointed'. My answer is more "the story of how they first came together roughly 250 years ago", including the influences on and the timing of that union. – JEL May 16 '17 at 9:16
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    Yes, clear and well documented. – user66974 May 16 '17 at 9:21

OED has a definition of pointed that suggests it is more related to making a point.

Marked, emphasized. Of attention, thought, criticism, etc.: directed unambiguously towards a particular person, subject, etc.; clearly making a point.

An example:

It was a pointed reminder to reporters..that the laws of libel don't stop at the borders of cyberspace.

In this sense, the word "pointed" meaning "to make a point" existed before its use to describe a question. One can make pointed criticism or a pointed compliment as well. It functions the same way in the phrase pointed question.

The notion that a "pointed question" has anything to do with knives is almost certainly apocryphal, given that the phrase has a clear etymological relationship with "making a point," and appears recently enough to have an established origin. (OED's earliest citation in this form is from 1768.)

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