Very interesting. I was in a very slightly similar situation regarding the dating experience you had (albeit with many more differences.) One source of consolation is that Hashem is pulling the strings. Which leads me to have pure faith that He is leading me to the right one-and you as well.
Im not sure about the dream. Personally many dreams I had were just random subconscious throughts, however I heard that a dream is what you interpret it as. This seems to be you interpretation and I guess that if its a possibility that his sister was hurt, is there any way to contact her? That may be an interesting thought. Especially since it seems that quite some time has passed by.