I had the same stumbling block. Even though intellectually it made perfect sense to me why Catholics prayed to and were devoted to Mary, after years of being an Evangelical and praying to God alone, it felt wrong praying to her. The mix inside just left me confused and unsure, unable to act. I thought of Scott Hahn’s first rosary, and I trusted that it was good. Yet I still was immobilized with confusion.
Then one night I could not stand fence-sitting any longer. I had a Memorare prayer from a little Mother Therese giftbook a Protestant friend gave me. This prayer just stuck in my mind.
So alone in my room, I got down on my knees and asked Jesus if it was okay for me to pray to His mother. And I asked Him to please stop immediately if he did not want me to pray it, because I did not want to displease him. And I listened, and I did not feel him tell me to stop.
So I began to pray the prayer, and it did feel so right, and I had confidence to continue. I prayed, “Are you my Mother?”, and I burst into tears. I hadn’t known how much I wanted to know that. And I asked her my intention: to please clear up my confusion over who she was.
At that very moment I realized I wasn’t confused anymore. And I never have been since. From then on, I KNEW she was my mother. It was a miraculous and swift answer to my prayer - my first prayer to Our Lady.
So if you want to have confidence and not have confusion about praying to Mary, ask her to help you. She will!
I also want to digress from this topic just to tell you what else happened after that.
At this time I had just begun my investigation into the Catholic Church. Hahn’s book had surpised me so. The Catholics really could be right. But I was not about to make such an important choice hastily. I would have to research both sides, and every issue. With my busy life, I figured that would take me ten years, at the very least…
That was February 1999 when I prayed that Memorare. Immediately I wanted to know how to pray the rosary. So I went to a really Catholic couple I knew, and asked her to teach me to pray it. Later she told me that she and her husband knew when I prayed that rosary that it wouldn’t be any time until I would be Catholic. They didn’t tell me that then. I wouldn’t have believed them.
But three months later, in May 1999, I knew. One Sunday, a series of events brought me to realize I needed to ask myself what I REALLY wanted. Just one thing. What was it. And so I asked myself, and I drew a complete blank. But the unanswered question nagged at me, and several hours later, late at night, it hit me. I wanted to learn about Catholicism, and to answer that quesiton about whether it was true or not. Finally satisfied - I knew my direction - I was able to sleep.
But I woke up in a panic. I realized that deep inside I really knew that if I began to investigate this, I was going to find out it was true. And if it was true, I was going to have to be - Catholic!
Not only did I not WANT to be Catholic (I really liked being Protestant) but there were many obstacles. They seemed insurmountable. It was the thought of them that me into a panic. I knew I could not face it alone, and as my mind raced for a way out, I thought of a group I heard that helped converts, and did an internet search to find Coming Home Network. Maybe they could help me. I was so afraid!
They did help me. They connected me with two very able mentors, who through email correspondance helped me navigate the very choppy waters I was thrown into. The conflicts and obstacles seemed huge, but by God’s grace my desire and determination grew and kept one step ahead of the obstacles. God gave me many graces. What a year it was. I knew almost immediately I wanted to be Catholic, so it was a trial to be patient and wait, but I did become Catholic Eastervigil 2000. What I thought would take ten years to decide took only about three months, and the decision seemed to happen of its own accord - not the ten years of laborious study I had predicted.
And it all started with that Memorare. So you see it really is true what everyone says - the fastest way to Jesus is Mary. I prayed to her, and in no time she had me before her son Jesus in the Eucharist! It wasn’t what I planned on, but - Mother knows best!

*Remember, O most gracious Virgin Mary, that never was it known that any one who fled to thy protection, implored thy help, or sought thy intercession, was left unaided. Inspired with this confidence, I fly unto thee, O Virgin of virgins, my Mother! To thee I come; before thee I stand, sinful and sorrowful. O Mother of the Word Incarnate, despise not my petitions, but in thy mercy hear and answer me. Amen. *