Emotional/non-factual question templates

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I've been working on Aspergers-related issues with a therapist, mostly focusing on handling dating situations better, and one of the problems I've been having (one of the skills I need to practice) is to ask more non-factual/emotional questions on dates.

Is anybody aware of resources for practicing these kinds of skills? In particular, I think it would be helpful if I could make a short list of question templates that I can learn draw on in conversation to open up lines of emotional communication. Does anyone know of a resource like this?

Welcome to WP!

I say ask questions like about your dates past. Of course ask how their day went and ask what they think of certain things e.g. your interests. Just work on it from there

So I ask questions about my date's past, and about what they're interested in. The problem is that at some point I delve into factual minutia along those lines of conversation, and it bores my date, and they don't want to see me again.

Then just remember, don't tell them facts until you know if they'll be interested or not, then you can garble about what they'll be interested in all you like.