There are similar verbs to "ask" in meaning or structure, such as "question" and "advise". Both verbs can take "on" as in the examples below, but why do native speakers feel "on" very unnatural only when it's used with "ask" unlike "question" and "advise"? I think that "on" can be used instead of "about" with "ask".

  1. The students were questioned on the books they had been studying.(O)
  2. She advises the government on environmental issues.(O)
  3. The interviewer asked me on my future plans.(X)

Is it because "on" sounds too formal to be collocated with "ask"?, or there could be ambiguity in the sentence?

  • It's not too formal. You can have "...quizzed me on..." in (3), and quiz is definitely less formal than "ask."
    – Kevin
    Dec 18 '18 at 3:05
  • @Kevin Then, it isn't definitely the problem of formality.
    – GKK
    Dec 18 '18 at 3:09

I am afraid that trying to figure out idiomatic English as a perfectly consistent set of rules is a hopeless task. In all five of the Indo-European languages with which I have some familiarity, the relationship between specific verbs and idiomatically associated prepositions follows no invariable rule.

All I can say is that "to ask on" is not idiomatic in modern American English; the idiomatic preposition is "about."

With your example of "advise," either "on" or "about" convey the same meaning although "on" does have a more formal tone.

With your example of "question," either "on" or "about" are acceptable, but I at least would prefer "on" if the questions pertained specifically to what were the contents of the books and "about" if the questions were not related to the contents. This preference may be just a personal quirk, but I probably would write

"They were questioned about where they bought the books that they were studying,"

but write "they were questioned on what they had learned from the books that they were studying."

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