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I also frequently show that I care about someone by trying to help them solve whatever problem they are dealing with, or offering any resources I have to spare, or I can share an experience that I had that I feel relates to what they are going through so show them that I can relate, but when it comes to feeling sympathetic toward's someone struggle or loss, it feels so foreign to me, and emotionless. I don't know if anyone else experiences this.
I'm the same way. I think in practical terms. But it also depends on the cognition of the person you're talking to - I had a relative who had a back injury and couldn't walk for a while, and while other members of her family were all "poor you," which just made her feel worse about her situation, I was doing her shopping and banking and renting her DVDs because she couldn't move around much, coming over to cook for her, taking care of all the practical tasks in an effort to demonstrate that I cared if she was bored or starved to death, so I would help. That, she said, was more helpful/supportive than sympathy, so maybe your style is fine too
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Alexithymia - 147 points.
Low-Verbal.