"Very truly I tell you, you will weep and mourn while the world rejoices. You will grieve, but your grief will turn to joy." (NIV)
It still totally amazes me how "the world" could go from the praise and worship of Palm Sunday to "crucify Him", within a week! Where did all the people go who were healed? Who witnessed the miracles? And yes, I know that it was all fulfillment of prophecy and the work of Sovereign God as planned and allowed by Him. This is how I would so easily identify with Simon Peter: "Peter took him aside and began to rebuke him. "Never, Lord!" he said. "This shall never happen to you!"" and I feel great pain in the response, "Jesus turned and said to Peter, "Get behind me, Satan! You are a stumbling block to me; you do not have in mind the concerns of God, but merely human concerns."
This happened over 2,000 years ago and I think most of us still struggle with this. If we truly love Jesus, then I believe His suffering would cause us pain, but if we truly love Jesus, then we also rejoice that He has accepted our death sentence for our crimes against Him. I know that we are not part of the Roman culture with public crucifixions, but personally, I can't handle to see anyone suffer, never mind rejoicing in anyone else's pain. According to this, it's ok to weep and grieve for a time, but yes, our grief will turn to joy. This might also be how it is with our close loved ones, too. Whether they're saved or not, we will miss them when they're gone and nothing can change that. We have hope, whether we know of their salvation or not; even moreso when blessed with knowledge of blessed assurance. The very best gift you can leave your loved ones is assurance that you will be in Heaven for all eternity.