If I say to you, “I’m sad” Do you actually know what I’m feeling?
We have words to describe different emotions, but there’s really no way to fully know how each individual person experiences them. We can only sympathize so far. When a friend is upset, we can imagine how we would feel in that situation, but we may not be picturing it correctly. We have different capacities for handling stress and emotional disruption. So we literally “feel” things differently. This can be unfortunate because when you are trying to sympathize with a friend, you could act either too calloused or overly sensitive.
The best way to compensate for that is to avoid projecting your own emotions into the situation, seek to understand, and let them create the picture for you as they talk and you listen.
And even if you never fully “get it” Your loved ones will appreciate your genuine effort toward understanding and that in itself will help to encourage them.