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"He should be ashamed to be laughing at his friends with the bullies."

I am quite aware that usually and most of the time the adjective ashamed is followed by "of doing", yet can that be substituted with "to be doing" in order to imply a progressive action?

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  • It's unclear who should be doing the shaming. Perhaps just "He should be ashamed laughing at his friends alongside the bullies." Or you may want to use "He should be ashamed of himself laughing at his friends with the bullies."
    – Phil Sweet
    Commented Apr 29, 2018 at 12:33

2 Answers 2

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Yes, this is fine. You are saying "While he is laughing, he should be ashamed", and this is a valid sentiment and a valid way to write it.

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  • I think 'of' is the most tense-less, with 'to be' close by, but 'while' adds a durative constraint.
    – AmI
    Commented Mar 29, 2018 at 23:05
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    It really is not fine. To be ashamed of something in English, verb or noun.
    – Lambie
    Commented Mar 29, 2018 at 23:12
  • Really, really not fine. Terrible, in fact.
    – Phil Sweet
    Commented Apr 29, 2018 at 12:36
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Yes, of course you can use to instead of of as a preposition in the sentence with ashamed.

  • I'm ashamed to say that the apple is not fit to eat.
  • He should be ashamed to be laughing.
  • He should be ashamed to laugh at his friends.
  • To be laughing at his friends with the bullies, he should be ashamed.
  • He should be ashamed, to be laughing at his friends with the bullies.

A comma was needed, to make the sentence more comprehensible. Also the suggestion given in the first answer was actually very good, too.

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