One problem the Christian Faith has in the world, especially the Dying West, is death by familiarity. That is, so much of the Faith is so engrained in our cultural mindset - even in today's wildly anti-Christian environment - it's no more special than a pair of shoes or an end table. In some cases, it's even worse. Terms, words, phrases have been captured, used, misused, mocked, derided, so that for many people, accepting various Christian doctrines is between believing in the Tooth Fairy and believing in Unicorns.
Words like demon, devil, Satan, angels, even heaven and hell in today's society are as simple-simon and pedestrian as butter churns and believing the earth is flat. For most today, Science(TM) has long proven there is no God, spirit, miracles or anything. It doesn't help that other doctrines, like Purgatory, have been dragged into the cultural wasteland and critiqued by other Christians in a negative light.
Truth be told, Purgatory is simply a word and concept that demonstrates what most Christian traditions affirm: that we're never perfect in this life, we then stand in perfection before God for eternity. With the exception of a couple holiness branches of the pietist movements, and the Orthodox Church - which believes we are never fully complete, even in eternity, but are ever improving and growing - the bulk of the Christian witness suggests something must occur between our last breath of this life and our first moment in the perfect presence of God.
Purgatory is the doctrine - and word - the Catholic Church uses to explain that gap between the here and now and the eternal perfection. As such, unless you're part of those couple pietest traditions or Orthodox, you shouldn't really have a problem with it. It's certainly better than what many in my old Evangelical traditions resorted to, and that was some variation on 'we don't know.' Are we immediately before the presence of God (see thief on the cross), do we 'fall asleep' only to be awakened on Judgement Day and then stand before the Almighty? Either way, there is still that moment when we are imperfect, and then the moment when we are made perfect.
As a convert, of all the Catholic doctrines I had to struggle with, this was the least difficult of them. Truth be told, I always found the Orthodox insistence that we never become perfect, and heaven is simply the next phase in discipleship (not how they frame it of course) a bit wanting. Certainly on a biblical level it seems to demand a few select readings of the texts. Based on what I learned of the Scriptures and the Christian model of Creation, Purgatory seemed to make all kinds of sense.
Therefore, praying for those in purgatory made as much sense as praying for those not in purgatory, but who are here on this sod. I can pray for healing for someone I'll never see again and never know if he is healed. Not knowing in that case doesn't mean I shouldn't bother to pray. Same with those souls undergoing that purging of the remnant of sinfulness we accumulate in this vale of tears. So we pray for them every bit as we ask them to pray for us. All Souls Day is the day set aside to focus on that part of the very ancient Christian witness to the communion of saints.
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