In Matthew, Jesus speaks a lot about the kingdom of heaven, and we must remember as a Jew that Matthew meant kingdom of God, i.e. where God rules. We need to divest ourselves of any sense of our permanent home being in the skies; heaven is where God is and comes to Earth with Jesus.
The parable of the virgins or bridesmaids is all about watchfulness for the bridegroom, i.e. Jesus, to arrive. Initially, this was about Jesus being revealed in his death and resurrection, for the parables were told to Jews after a discussion about the temple, yet of course it applies to our own situation as we wait for Jesus to return.
The paradigm of foolish versus wise harks back to the wisdom literature. The fear of God is the beginning of wisdom. This parable doesn't speak of pragmatics in the first sense, having enough oil, but about being wise toward God rather than foolish. This is all about moral categories. Do you believe that Jesus is the Messiah and expect him to come into his reign? For the disciples, they should watch and wait for the time when Jesus would be crucified, the temple destroyed, and us for Christ's return.
Of course, being in a state of preparedness means a good deal of things, but it doesn't amount to anxiety over whether or not we've done enough, but just having faith. The rest should follow (as faith without works is dead), but it doesn't mean going to bed at night anxious or showering in your underwear in case you are suddenly raptured. Just be a faithful bridesmaid as we weight for the groom.