Overcoming Overstimulation(mostly thinking of relationships)

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I'm putting this in "Love and Dating" because although I want to talk about some of these in other relationships, I want to target dating, mainly.

Anyways, I'm uncomfortable with showing how I feel. It's uncomfortable and overestimating. I'm better with it, now but not where I feel I should be. One thing that is a problem is when someone is having a hard time or is sad. I can't say anything. Maybe I worry about being judged, but that can't be all.

This might be not so good in the dating side off things. Maybe I'll feel different if it's a live interest. Maybe not. And then that's physical affection (hugging). I'm not one of the ones that hates the idea of it. In fact, I think about it a lot. I want to. But with friends if it's done to me. I shut off any feeling. I find that a little sad and if it was with a special someone that's seen even more sad.

So do people with this kind of overstimulation get better in this area?

I understand this, when I know people are upset, I know what the expected thing to do is, but I don't feel comfortable doing it...I've tried and it's just awkward.
An example of this is when one of the mums from my sons school walked out to find her car had been broken into and quite badly damaged, she stood shaking and crying, all I could do was tell her to call police, insurance and organise a tow truck etc, I helped her with the practical things. Someone else walked over and put their arms around her, hugged her and consoled her.

However I'm learning, on the last day of school another parent who runs the religious programs (so I have had to meet with her a few times) sat next to me and started pooring her heart out about her husband leaving and not seeing the children etc, she was sitting beside me rather than infront of me which helps a lot. I did put my arm around her and told her that nothing I said would make it any better and that its ok to be upset and that its ok to let your children see you upset as you are showing them that it's ok to grieve..... In the end she thanked me for not trying to placate her apparently I was the only one who didn't.

We Aspies don't connect well when it comes to feelings. I unfortunately have this problem in full scale. Emotions are quickly shut off when you're trying to connect with someone emotionally.
You just gotta work on it. Don't worry, it's not that difficult