One question I run across quite often can be worded as follows: "How will I enjoy Heaven if I know some of my unsaved loved one's are suffering in Hell?" For now, I can only think of 6 possible answers to this question. Which position(s) do you hold?
1. We won't remember 'lost' people
2. Joy will outweigh sorrow
3. We'll understand justice and be content
4. We'll find out that the wicked are annihilated
5. We'll find out that the wicked are converted
6. Joy in heaven doesn't imply an absence of grief