She is blessed, both in the traditional sense (literally, "happy") and in the more modern sense (more like "good things happen to me"). Seriously, what doesn't she have to be happy about? Conceived without sin, betrothed to a chaste and loving man, visited by an angel, building with her own body the very flesh of God Himself, raising Him and caring for Him...the Prophecy of Simeon, the flight to Egypt, losing her Son for three days, watching Him carry a cross and be crucified, taking His lifeless body from the Cross and laying Him in the tomb... wait a minute, those are the Seven Sorrows!
Through all of these sorrows - some of which are surely the deepest and most profound sorrows that one might experience - she is the most blessed, the happiest among all women. Because she never doubted, never feared. She knew God's plan: as terrible and horrifying it was to see Him crucified, she knew that He would rise, and that His Resurrection would bring us all to new life. So, yeah. Why shouldn't she be the most the blessed woman to have ever lived?
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