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I came across this question in a test:

The father regretted _____ his children how he regretted _____ hard when he was young.
A. to tell; not to study
B. telling; not studying
C. to tell; not studying
D. telling; not to study

I know it’s either B or C and I’m inclined towards B. But can “regretted to tell” mean telling something embarrassing here?

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    He remembered to tell ... ; he remembered telling ... ; he regretted telling ... are all fine, but he regretted to tell is not. I am not sure how to explain this in terms of grammar, but it doesn’t sound correct ! – k1eran Oct 13 '18 at 13:40
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    @k1eran has it absolutely right. Whereas remember can take either an infinitive or a gerund complement clause as object, regret can only take gerunds; with an infinitive, it produces ungrammatical sentences. Every verb that can take a complement clause has its own set of affordances -- clause types that are required, optional, or forbidden -- and they all have to be learned individually. – John Lawler Oct 13 '18 at 14:49
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    I regret to inform you that Mr. Lawler is not quite correct in his opinion. Moreover, we regret to inform you is fairly ingrained in the popular mind, and can be used outside of official communications in a way that connotes the falseness of the sentiment being expressed. – Global Charm Oct 13 '18 at 20:51
  • There's something quite strange with "regret". In its present tense the infinitives it's mostly followed by are to inform/tell/say/advise, but you can also find "to hear", "to disagree", and "to interrupt", common to a greater or lesser extent. So it seems to acceptably take some infinitive verbs but not others. In other words I have no idea which infinitive verbs can and can't be used with it. – Zebrafish Feb 18 '19 at 3:21
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It’s C.

He regretted to tell his children.

Because we commonly say ‘I regret to tell you that your application has not been successful’ or whatever.

And it’s ‘not studying’ because it was continuous - the not studying went on for a while.

And yes - he could feel embarrassed about it - ‘regret to tell’ means ‘sorry to tell them’ - about his own wrong-doing, so he might feel ashamed or embarrassed that he was not innately a good example to them.

https://www.macmillandictionary.com/dictionary/british/i-we-regret-to-inform-tell-you-that

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    Sorry but the correct answer is B because the question sentence is in the past tense. The example you give, "We regret to inform you...", is in the present tense. If a person who had said "we regret to inform you that.." later referred back to the previous occasion they would say either "we regretted having informed you" or, more commonly, "we regret having to inform you that..." – BoldBen Jan 19 '19 at 2:45
  • ‘He regretted to tell them’ is in the past tense. So I’m not sure what you’re saying here. – Jelila Jan 20 '19 at 5:12
  • I'm saying that the past tense of a verb is usually followed by the present participle of any second verb whereas the present tense is usually followed by the infinitive of a second verb. For example "I regretted saying" and "I regret to say". This means that invoking "I regret to say" as an argument that "I regretted to say" is correct does not hold. – BoldBen Jan 21 '19 at 13:19
  • @BoldBen No, not usually. This is a peculiarity of regret: present-tense forms can take either infinitive or gerund complement clauses (with slightly different meanings), but past-tense forms can only take gerunds. This does not hold for other verbs, though: prefer can take both infinitives and gerunds in any tense; enjoy can take only gerunds in any tense; and want can take only infinitives in any tense. The sort of ‘split’ licensing we see with regret is not the norm. – Janus Bahs Jacquet Feb 18 '19 at 0:16
  • However, Ben is right that the only correct option here is B, not C. With an infinitive, regret means something like ‘be about to [verb], but feel bad about it’; with a gerund, it means ‘wish you hadn’t [verb]ed, but it’s done so you can’t change it’. The former is pretty much exclusively used in the simple present tense, whereas the latter is freely usable in all tenses. The example in this question is past tense and carries the latter meaning, not the former, so it must be the gerund, not the infinitive. – Janus Bahs Jacquet Feb 18 '19 at 0:23

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