The Rosary, no longer a difficult prayer
Growing up in a Catholic school run by nuns, the months of May and October were always dedicated to Mary. Our teachers distributed rosary coloring sheets and we could color one for every rosary we recited. The students who prayed the most rosaries at the end of the month would receive a prize. So, most nights I would walk to a small outdoor grotto dedicated to Our Lady of Lourdes built in my neighborhood after WWII. (http://www.borgotrentoverona.org/index.php?module=content&func=view&pid=144). There I would pray the nightly rosary with a few older ladies. Sometimes, I would get to the grotto 15 minutes early, so I could rush through another 5 decades before everybody showed up, allowing me to color two coloring sheets. I don't remember if I ever won a prize, but I know I got bored and distracted.
I think it is safe to say that most Catholics under the age of 70 find the Rosary boring, too long or even a needlessly repetitive prayer that is hard to understand. This was surely true for me until I recently attended a talk about the Blessed Virgin Mary by Dr. Edward Sri. Apparently, even for him, a well formed Catholic apologist, the Rosary was not easy until he read a reflection by Saint John Paul II (JPII).
JPII explained that the Rosary is actually a Christ-centered prayer. This was great news to me, because I have had a hard time understanding why we would pray 50 Hail Marys but only 5 Our Fathers and 5 Glory Bes.
You can read the complete reflection by Saint John Paul II at https://w2.vatican.va/content/john-paul-ii/en/apost_letters/2002/documents/hf_jp-ii_apl_20021016_rosarium-virginis-mariae.html, but here is a quick summary of it.
The first words of the Hail Mary are biblical words spoken by the angel Gabriel, "Hail Mary, full of grace, the Lord is with you" and then by St. Elizabeth, "Blessed are you among women and blessed is the fruit of thy womb." Our faith teaches us that the angel is a creature that God created on the first day when he separated darkness from light. Since then, the angel Gabriel has been glorifying and praising the omnipotent God until one day God asks him to leave Heaven and go to a tiny planet called earth, to a tiny town called Nazareth, and to a human creature, a very young woman, to speak the words that announce the Incarnation of God.
So, the words of the angel Gabriel become words of awe in the incredible mystery of God becoming man. The angel speaks words of excitement and joy in announcing to Mary what is to happen to her and he praises God for it.
Similarly, when Mary visit her cousin, we read that Elizabeth was "filled with the Holy Spirit". She also speaks words of wonder and of praise for the mystery of the Incarnation and of God's bounty! How could Elizabeth have known that Mary was pregnant anyway? It is not because Mary had changed her status on Facebook, as Dr. Sri joked during his talk.
So, when we pray this part of the Hail Mary, says JPII, we are united with both Heaven (the angel Gabriel) and earth (St. Elizabeth) in the joy of proclaiming the mystery of salvation through the incarnation.
Then in the Hail Mary comes the most important word, "...and blessed is the fruit of thy womb, JESUS." Saint John Paul II calls it the hinge or center of gravity of the Hail Mary. And to truly make it the center of the prayer, let's consider adding a few words to it, based on the mystery that we are reciting. So for example, ""...and blessed is the fruit of thy womb, Jesus who is being born", or ""...and blessed is the fruit of thy womb, Jesus, who is ascending into Heaven".
And finally, the last part of the prayer is an invocation to Mary to be our mediatrix and to pray for us, now that we may do the will of her Son and in the hour of our death.
Like a wife is never tired of hearing her husband tell her, "I love you", we can be confident that God is also never tired of hearing us praise him through his earthly mother.
After hearing this reflection, I now actually feel excited about praying the Rosary, because I can understand it better and I can see how Jesus is truly its focus.
And don't feel discouraged about getting distracted at times. As St. Thomas Aquinas said, because you are praying biblical words, you are still giving God a gift, even if you are doing it imperfectly.
Here is a link to Dr. Sri more detailed explanation: http://www.cuf.org/2008/09/praying-the-hail-mary-like-never-before/