... every time I have tried to ask him ...

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Maybo

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I can't shake the feeling that he's hiding something from me. Why has he been so evasive every time I have tried to ask him about Kelli? He already told me he went out with her. Why won't he admit it?

Source: The Inmate by Freida McFadden

Why did the writer use “have tried” instead of “try”?
 
The trying was in the past and runs up to the present time. It matches the tense in the opening of that sentence.

Why has he been so evasive every time I have tried to ask him about Kelli?
Every time I have tried to ask him about Kelli, he has been evasive. Why?

To use "try" in that part, the opening would be "Why is he so evasive ...".
 
Another question is why the writer used “went” instead of “had gone”?
 
He is backshifting in reported speech. His actual words were "I go out with her".
 
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Q: Why did the writer use "went" instead of "had gone"?
A: The phrase "he went out with her" means he dated her. He went out with her on dates. They went places together. They enjoyed each other's company.

How do you suggest "had gone" should be used? (I'm having trouble thinking of a way to use it.)
 
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How do you suggest "had gone" should be used. (I'm having trouble thinking of a way to use it.)
"I go out with her." - He told me he went out with her.
"I went out with her in May." - He told me he had gone out with her in May.
 
I can't shake the feeling that he's hiding something from me. Why has he been so evasive every time I have tried to ask him about Kelli? He already told me he went out with her. Why won't he admit it?
Since the whole thing runs up to the present (i.e., they go out together), the author could also have used the present tenses for the bolded verbs:

I can't shake the feeling that he's hiding something from me. Why has he been so evasive every time I have tried to ask him about Kelli? He's already told me he goes out with her. Why won't he admit it?

Am I right?
 
He is backshifting in reported speech. His actual words were "I go out with her".

I don't think that's what it means. I think the speaker means he used to go out with her in the past but not now.
 
Yes, it could also mean that.
 
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