I ended a good conversation.

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I recently contacted an old friend who I had "chemistry" with for three years as advised by my therapist. I opened the conversation asking a computer question and then asking him about college. He then answered both questions and asked me about my plans.

Very hesitantly, I congratulated him on some of his recent accomplishments and responded with a very vague account of what I might or might not do with my life, and I did not exactly leave the conversation with anything to continue on. I doubt he will (being also socially awkward) respond to such a vague response.

The thing is that I still do care about him and have floated the thought of us being in a relationship in the future many times, but I don't know if my anxiety will be too much of an obstacle, as it certainly was in simply trying to contact him by email.

Any advice would be appreciated. Thanks.

If he won't respond because there was nothing to respond to, you can always send another mail with another question. If he is Aspie-like though, he might still respond and talk about something else, so give him some time.