I recently received a question via email from a non-Catholic who is truly pursuing a search for Jesus in her own life and is in the process of discernment:
The concepts that are more difficult for me are things like praying through Mary and the saints."
These concepts are difficult for many Catholics as well.
I try to think of it like this:
We have mothers on Earth. These mother's give us a certain type of love—a love that no one else can give. They hold us in their wombs from conception until birth in the world, then they nurture us physically, spiritually, and mentally for many years. Without our mothers, we miss a lot of the love that is necessary to truly become one with Christ in his sufferings and his glory.
In much the same way, we are advantaged to be able to go to our Heavenly Mother, Mary, in times of trouble, or to find love. She is like our 'perfect Earthly Mother'. Who better to show us Jesus than His Mother? She nurtured Jesus from the time of His conception onward. She was there with Him on the road to Calvary; she was there for him when he was on his cross, dying in reparation for our sins—even though many others were not.
Mary went through grief and trials of faith and love, just as any loving mother does. She was, perhaps, the person closest to Jesus on Earth, and she is now close to Him in Heaven. What better way to speak to Jesus and to know him better than through Mary? Sure, we can pray 'straight to Jesus'... but what if we could also have Mary and other saints intercede for us?
Is that not what we do on Earth when we pray for our brothers and sisters here? We pray for each other here, but imperfectly (as we are not made perfect until we enter God's Kingdom). Is it a waste of time to pray for each other, or to request that someone pray for you? If it is a good thing on this earth, how much betterwould it be to have former Earthly companions who are now in Heaven (Mary included) to be praying for us as well?
That is why Catholics are not ashamed to pray through Mary and rest of the communion of saints, both heavenly and earthly.
For more reading on this issue, I highly suggest:
Hail, Holy Queen: The Mother of God in The Word of God (by Scott Hahn)
And Catholic Answers' Library: Mary & the Saints
UPDATE: This topic is continued in a post on January 5.