Context: In the previous chapter Matthew records Jesus's conversation with His disciples about the 'signs of the end of the age'. One of the fundamental teachings of the Christian faith is that Jesus is coming back a second time, and when He does it will usher in the beginning of a new age. In this new (and final?) phase of history, everything as we know it will change. God will make it better. The Bible teaches that we live in a world that is a far cry from the place He created it to be. The reason: human beings' disobedience brought a curse on it. Jesus disciples were intrigued about the timing of His second coming, and He told this parable to show them how they should wait for His second coming.
Comments and Application: We need to be ready for Jesus's second coming at any moment, because it will be a complete surprise. The parable suggests that it will feel as if a long time is passing before He comes again, and that it might be so long that we may drop our guard.
The parable also suggests that we can and have to live our lives in such a way that we are prepared for Jesus's second coming. Five of the virgins planned and invested ahead in such a way that they were ready for the bridegroom's arrival, even though it was a little unannounced. The other five were lazy and careless, and wanted to prepare themselves for the bridegroom's arrival at the last moment. There will be no place in God's Kingdom for people whose actions don't mirror the attitude of their hearts.
Jesus's final comment explains this parable, "Therefore keep watch, because you do not know the day or the hour". We need to be vigilant in our pursuit of living for God: we don't know when our time in earth is over, and we don't know when Jesus is coming again.
How will Jesus find you if He returns today? Prepared, or unprepared?