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The single biggest question surrounding the Second Coming is: what's the freaking hold-up? The earliest Christians believed that Jesus' second coming was imminent, a view seemingly held by Jesus himself: in the Bible he tells some listeners they will still be living when the event occurs. Paul too seems to think that this will occur when some of his current followers (and himself) are still alive.
Some Christians try and argue that Jesus had limited knowledge in his human form and made a mistake. This runs contrary to the widespread Christian belief that Jesus was both fully God and fully human. This also leads to another problem: how many other teachings of Jesus are mistaken? Complex efforts at apologetics are made which try and explain away this failed prophecy, but, using Occam's Razor, the simplest and most plausible explanation is that Jesus or whoever wrote that account predicted something that failed to happen. Certainly the early disciples expected Jesus to return during their lifetime and Jesus either was not omniscient and overlooked the misunderstanding or knowingly deceived his own disciples. Others argue that when Jesus was saying Kingdom he was not talking about the Second Coming, but the Transfiguration. Granted that that's a way out, but it's scripturally dangerous to suggest he didn't really mean what he said.
Second Peter (written many years after Paul's epistles) addresses this issue by saying a thousand years is equal to a day to God. So to God we're just starting the third day since the crucifixion. No rush. Although this very reasoning leads some literalists to assume that the Universe was created over the course of 6,000 years.
Some preachers have made startling predictions regarding the second coming. Some notable ones include William Miller's great disappointment of 1844, the Jehovah's Witnesses prediction of 1914, and the most recent prediction of Harold Camping of May 21 2011.