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The question assumes that upon death the righteous immediately will ascend to heaven to be with God. I’m well aware that for many Christians this is a much-beloved doctrine, however, the Bible is saying nothing about such an event. On the contrary, the Bible says that the dead do not praise the LORD (Ps 115:17; Isa 38:18, 19); they know nothing and that upon death our "thoughts perish" (Eccl 9:5; Ps 146:4). The departed know nothing and are unaware of the passage of time. Moreover, Paul taught that the dead in Christ are "asleep" in their graves awaiting the resurrection. When the elect who "sleep in Jesus" are resurrected at Jesus' return (1 Cor 15:51-54; 1 Thess 4:13-17) their consciousness returns. Then, along with those "which are alive and remain," they rise to meet Christ. Nowhere does it say they meet Christ before then. And they meet Him "in the air," not in heaven. In John 14:3 Christ promised to return to take us to be with Him. If when we die, we immediately go to be with the Lord, Jesus' promise makes no sense; we are already with Him, no need to come back for us. In his 2nd letter to Corinthians, Paul is not saying that immediately upon his death, he will be transported in the presence of the Lord (2 Cor 5:8). He is simply saying that rather than being here in this world full of suffering, he would rather be with the Lord. In his 1st letter, Paul talked about what will happen at Christ's return (1 Cor 15:51-54). For those resurrected it will seem like no time had passed since their last conscious moment at death. Paul understood that after death, the next thing he would know would be that he had been resurrected and was meeting Christ. It would make no sense for Paul to tell Corinthians that he will meet Jesus immediately upon his death while telling the Thessalonians they'd have to wait for a resurrection to meet Christ. Paul hoped to attain the same resurrection he told the Thessalonians about (Phil 3:10,11). In conclusion and based on what the Bible says, I believe that the dead are just dead in their graves, oblivious of what is going on here on earth or in heaven.
When Christians die our souls are instantly transported to heaven to be united with Christ. We know that our souls are in heaven from the descriptions in Revelation. The twenty-four elders are worshipping Jesus (Revelation 5;8); a great multitude that no one could count from every nation, tribe, people and language was standing before the throne and the Lamb, praising God's salvation (Revelation 7:9); and the souls of the martyrs under the altar are crying out to God for justice (Revelation 6:9-11). Heaven is a perfect place and our existence there is perfection. Jesus has already prepared a mansion for each of us in heaven. Jesus describes what heaven is like in the book of Revelation, with the detailed description of the New Jerusalem that comes down from heaven to dwell on the new earth, see Revelation 21:1-27. The present earth is a dying world filled with evil, wickedness, corruption and decay. God would be cruel to allow us to view all this sin and suffering, instead of enjoying the bliss of living in the presence of God and worshipping with the holy angels.
To my knowledge, the Bible is silent on this subject (saying neither whether they can or cannot). Some people cite the reference to the "cloud of witnesses" referenced in Hebrews 12:1 as an indication of the "heroes of faith" being able to see us, but I would say that "witnesses" in that sense refers to the example that they provided, rather than to their eternal state. However, in my opinion, the redeemed would likely be so engaged in worshipping and praising God, as well as experiencing the joy and blessedness of their eternal state, that for them to continue to be concerned with affairs on earth, or to have visibility or knowledge of them, could only compromise or dilute that experience. It would seem to me to be an extension of Jesus' earthly caution (to the man who wanted to bid farewell to those at home before following Him) against looking back after you have put your hand to the plow (Luke 9:61-62).
My answer to your question is this: Since we know there are no tears or suffering or disease of any kind in heaven, they could not possibly look in on us. Even the Father had to turn from Jesus as he was on the cross. So as much as I would like to think my mom and dad can look down at me, I don't think it's possible.
Hebrews states that we as Christians are surrounded by a great cloud of witnesses who cheer us on. Therefore they are watching us and know whether we perform badly or well in our walk as Christians. The rich man could see Lazarus from hell and so could Abraham from heaven. There are also several places in the gospels where it states that the Father God spoke and therefore could see everything that was going on: At his baptism At the Mount of Transfiguration And on the cross Jesus knew that His Father had forsaken Him
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