If someone asked me if I regretted something, how can I express if even his/her assumption that I regretted something surprises me? In my mother tongue I would answer with a question like "why would I have regretted it?", but in English it seems unnatural to me. What do you think?

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    Your example, "why would I have regretted it?" is perfectly good and understandable. I would say that as a native speaker myself. – Kristina Lopez Nov 17 '14 at 18:42
  • I agree with Kristina. As a native speaker of English, I would also say, "Why would I have regretted it?". – Babs Nov 17 '14 at 18:49
  • It is surely not the best measure, but I was surprised to see that there is only 2 Google results containing the exact phrase, while both the words and the situation seems pretty ordinary. – Gergő Nov 17 '14 at 18:50
  • There are 11 citations for why would I have [v?n * ] in COCA. – tunny Nov 17 '14 at 18:55
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    The "unnaturalness" has probably already been shown by whoever asked "Did you regret that?" in the past tense. Nine times out of ten even if you did regret it in the past, you still do now, and the natural question to ask is "Do you regret it?" – FumbleFingers Nov 17 '14 at 21:09

It doesn't sound unnatural to me at all, although the simple present tense might be more appropriate than the present perfect if the question was posed in the present tense (which suggests that you might still be feeling regret up to the present moment):

Q. Do you regret doing it? (or Do you regret having done it?)

A. Why would I regret it?

The present perfect is better if the question was posed in the past tense:

Q. Did you regret doing it? (or Did you regret having done it?)

A. Why would I have regretted it?

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