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I hand a picture to a friend. That friend takes a look at the picture.

Me: When you look at that/this, what does it make you feel?

If I refer to the picture (I don't have it in my hand; my friend does) or maybe more the thing that is on the picture, what is natural "that" or "this"?

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Either would be understood in this case as long as there’s only one picture, but “that” is better if your friend is holding the picture at the time you ask. If you asked while holding it or handing it to them, “this” would be better.

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