The parable about the beggar Lazarus and the rich man told in Luke 16, indicates an awareness of each other from both heaven and hell. So much so, that in Luke 16:26 it describes a gulf between the two dimensions to prevent crossing over. Are you aware of the souls in hell if in heaven and vise versa? Will we see ones we could have witnessed to in agony?
The Church does not speak definitively on this. Below is an answer from a good and holy priest:
"As to the issue of knowledge of the souls in hell when your soul is hopefully in heaven, scripture seems to indicate that when we are perfectly united to God, we will have full knowledge in all things. St. Paul make several references to that in his letters. We will become like God, which automatically means we will have knowledge like God. And if at St. Paul said, that God will be all in all, then we will have that fullness of divine knowledge. However, I think we will be so taken upinto the love and the mystery of God's presence, That we will not focus much if at all on the soles and help. If we are totally focus on God in heaven, and God is all in all in heaven, then knowledge of the souls in hell could possibly create unhappiness for us. But we know from St. John in the Book of Revelation, that the new heavens and the new earth will have no more sadness, weeping, or pain. Therefore if that scripture is true, we cannot be sad about the souls that we might know are in hell. I hope that answer helps you!"