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One word answer for the question "Why did Jesus Weep?" is his "compassion" for people. Jesus feels the sorrow of his people and feels sorry for it. Shows compassion and if they come to him begging for deliverance he redeems them. But as human beings we can not fool him, or cheat him for he knows our every heart and every thought that comes to our minds! He demonstrated it by trapping the Jews by their own answers or actions who cunningly questioned him to trap him in his own words. There are many instances in his life and public ministry where he was moved with compassion and either said or did something to delver the people from misery and sickness. In the wedding ceremony when his mother said " They have no wine", he first ignored it but then he turned the water into wine for the sake of his mother's trust in him. He healed the blind man who kept on crying for healing him. He healed the lepers and the man near the pond going near to him. He raised the widow's son from death seeing their wailing. He healed the bleeding woman who silently touched his garment, He healed the boy possessed by demon. He fed the multitudes who were hungry since many days, He showed pity on Mary Magdalene and forgave her. He showed pity on the good thief and promised him the paradise. He showed pity on the army of demons and permitted them to enter into the pigs and because of which the people off that place pleaded Jesus to leave their town. He even prayed for his persecutors and pleaded his father not to hold them responsible for their sins or punish them. Similarly Jesus was moved by the wailing of Mary, Martha and the Jews gathered there and also showed them he too was human like them and felt sorry and sorrowful when his loved ones cried and experienced the sorrow in their hearts. So these incidents of Jesus showing compassion, weeping with the people and praying for his disciples or people shows us how compassionate and loving he is towards the human race and wants to save them all. We are lucky and fortunate to have such a master, friend, companion and Lord who doesn't abandon us in our sorrows and miseries. We only need to trust him and pray to him. He is sure to help us. He preached it in his teachings the prodigal son, The unjust judge giving justice to the widow, the lost sheep, the lost coin, not to worry what to eat and what to clothe, knocking at the door at midnight for help, talking to Samaritan woman, addressing Judas as friend even in betrayal shows us our Lord Jesus is so compassionate and loving that he is even available to us today in the same manner whatever we may be or how ungrateful and careless we may be towards him and his father so far.
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