What was it that Jesus found attractive in fallen women like Mary Magdalene and the woman by the well? He recognized the hopelessness of their situation and being a man with feeling, he sympathized with them. Christ, as we will never understand, was a man with feeling.
I once mentioned that God is a being who loves paradox (an apparent contradiction). Christ fulfilled the requirement for that in being at the same time God and a man. As a man he had an uncanny insight into what makes humans tick. I hope He sympathizes with me on the last day.