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Jesus became known as the friend of sinners, and we are all sinners. He befriended all who were open to his teaching and who wanted to get close to him. Specifically mentioned are tax-collectors and prostitutes. And his friendship was not dependent upon their repentance. He would get to their sinfulness when, and if, they wanted to open their hearts to him.
Given that Jesus is the friend of sinners, what should I be like? Jesus said: As the Father has sent me I am sending you. This means I too need to be known as a friend of sinners. It should be obvious to all that I will associate and befriend anyone, no matter what those around me – even fellow believers – might think.
There is perfect harmony in the Godhead. So, are the Father and the Holy Spirit also the friend of sinners. Yes! They all share exactly the same heart towards us all. When Moses asked to see God's glory, the Lord caused his goodness to pass in front of him and proclaimed himself as merciful and compassionate. Moses had asked to see the Lord's glory and God showed him his heart. His compassionate heart is his glory!
"The Lord, the Lord, the compassionate [merciful] and gracious God, slow to anger [literally "long nosed" as opposed to "short nosed" like an angry bull pawing the ground ready to charge], abounding in love and faithfulness, maintaining love to thousands [or "keeping steadfast covenant love to a thousand generations" (Dt. 7:9)], and forgiving wickedness, rebellion and sin" (Ex. 33:18-19; 34:6-7).
What is the Father's heart like? He is "the Father of mercies [plural: compassions of every kind] and God of all [every kind of] comfort" (2 Cor. 1:3). The Lord God is "full of compassion and mercy" (Jm. 5:11). God has a tailor-made mercy for every sin, sickness and misery and a perfect form of comfort precisely appropriate for every one of our needs. It is his hearts to shower mercies and comforts of every kind upon his children.
Although we will all stand before the Judgement Seat of God, in this life he is not judgmental! And neither is the Holy Spirit. Jesus called him another Counsellor who would replace him as his disciples' teacher and never leave them. He would remind them of what Jesus had taught and glorify Jesus to them.
Jesus told the Jewish religious leaders: "Tax collectors and prostitutes are entering the kingdom of heaven ahead of you … and even after you saw this you did not repent" (Mat. 21:31-32). Why were the most despicable kinds of sinners known in that culture entering the kingdom of heaven? Because Jesus had befriended them. They couldn't stay away from him. They were at ease around him. Others held them at arm's length. Jesus drew them into his heart.