Your point about what kind of response is wanted is well taken. I can understand that he may have no idea what I am looking for so I need to be clearer in my communications. I was, I guess, just hoping he would share his feelings in reaction to the things I said but I have never clarified this for him and need to do so. Not sure if this is actually an NT/AS issue or a female/male issue. I think maybe the latter in that females seem more inclined to give to feeling responses to expressions of emotion.
This could be a combination of the two things, as well.
I'm trying to understand what you mean by "feeling responses" ..... I don't really understand what you mean, especially when you're talking about text communications. (In person all sorts of things communicate feelings, and could be what you mean.)
Do you mean something like this(?):
You: I feel [emotions] about [thing that happened]
Friend: I would feel [similar or identical emotions] about that too.
If it is this one, then I would suggest that you ask your friend, "How would you feel if this happened to you/if you were in my place/about [name/description of thing that you have feelings about]?"
Or like this(?):
You: I feel [emotions] about [thing that happened].
Friend: That is/sounds so [emotions to describe a situation -- e.g. frustrating, joyous]
If it is like this one, is it accurate to say that at least part of it is you are hoping for your friend to share in your feelings, or hoping for validation?
I am not sure how to ask for something like this more specifically....validation (or the validation part, if it is more complex and validation is part of it but not all of it) is easier because you can just say, "I need/want/am looking/hoping for some validation".
Any shared feelings aspect is more complicated....I don't know how to ask for it, because unlike asking for how he would feel it's more like asking him if he can feel what you feel (what I'm referring to -- you might not ever even want this or anything like it, I make no assumptions here).....
You could ask something like like, "Can you imagine/understand how I feel?" but then you might just get "Yes" or "No" as an answer if you don't explicitly tell him you'd like him to then narrate his imaginings back at you to show his understanding....which I think might sound really weird (even though this is something people want and receive from each other all the time) because I have never heard anybody explicitly ask for it. (Which may not matter at all to you or your friend....I have lots of memories of people saying to me, self-consciously that they sound weird but even if I suppose after thinking about it that it is weird, it wasn't like it struck me as weird at the time and I don't actually care -- weird is all good with me. I do and say weird things all the time, so it's not a problem for me if other people do or say weird things.)
Or something like this:
You: [Either of the above "You" statements, or you tell a story that doesn't actually contain "I feel" statements or feeling words but that contains other expressions of emotion -- like specific words or phrases that generally connote specific feelings]
Friend: I [am/feel] [emotions] for you. [Or something without any actual description of feelings but that connotes emotional experience, like "That must have been awesome/terrible for you"]
I have no idea how to go about asking for this explicitly and I have given myself a headache (an actual headache that I'm going to go take something for in a moment) writing this so I need to stop now....