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I came across the following question and found it strange. When have you felt insecure because you were a first-timer?

Shouldn't it be "when did you feel....?"

Thank you

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No, the tense is appropriate.

It is written in the present perfect because it is asking about any moment in your past up to the present at which you might have felt this emotion.

Beginning the sentence with when is a little confusing. It would sound perfectly idiomatic if we just asked: Have you felt insecure because you were a first timer? meaning have you felt insecure for this reason.

The question could also be phrased in the past tense but would fit more comfortably into a different context, one in which the questioner already knew that you had felt insecure but wanted to know when - what had caused you to feel that way:

When did you feel insecure because you were a first timer?

So both constructions are idiomatic. Their likely use really depends on the context.

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  • Starting the question with "When" seems to ask for a time or time period in the answer. "When did you feel insecure?" / "Last year before I passed the course." "Have you felt..." seems to ask for a yes or no answer. Note that "feel" could refer to a physical feeling, depending on the context. "When did you feel dizzy?" / "Right after I stood up" Mar 24, 2019 at 16:56

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