Response
I agree with you Gwendolyn that we do have the ability to connect with other people and their experiences in perhaps an unexplainable way, but then later on you said that you choose to never say "I know how you feel". But I'm curious about that because when we connect with people in that mysterious way (perhaps over having been through similar experiences in the past), don't we have to at least be implicitly saying "I know how you feel" or "I know I'd be feeling really bad if I just went through something like that"? Don't you have to be implicitly saying this when you try to empathize with someone else's situation, even if you never explicitly say so?

I don't think you can actually "know" how someone feels if you have not went through a simialar situation or circumstance. If you don't have any siblings how can you feel the pain of someone loosing their siblings? If you have never experienced homelessness how can you say how it feels to actually have to live on the streets? How could you feel the pain? A person who has won $25 Million(A) and a person who has never won anything(B); B can only imagine the emotion of winning a jackpot whereas B has felt some sort of emotion.
I believe that our unconcious mind automatically implicates a feeling/emotion/reaction for us; but if we were not directly affected/involved we will never actually know the true feeling.
So, if I have not been through your situation I can only say what I think or could imagine whereas if I have been affected in the same manner I can say what I "know".
If what you mean by know is "to have gone through a very similar experience as someone else", then you're right, you won't know what it's like to be homeless or to win $25 million dollars unless you've actually experienced it yourself. But as Fay points out in our text, experiencing does not usually mean the same thing as knowing. A historian does not necessairly have to experience something similar to being a homeless child during the Middle Ages to be able to write about them, learn about them, and teach others about them. Doesn't the historian "know" what their lives were like, at least in one sense?