Mary was not sinless.It is surprising that many don't look at the words of the prayers like the "Hail Mary". Basically, we are asking her to pray for us. Just as many as others to pray for them - we ask Mary to pray for us. What better person than one without sin who is Jesus' mother?! I prefer asking Mary to pray for me than another who is not free from sin.
That is all it is about.
When I pray the rosary, I also pray directly to God and I remember the life of Jesus in the stations of the cross that are also said on that rosary. It focuses my mind on His life and death for not only me, but for all of us.
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