JESUS - FRIEND OF SINNERS. (Matthew 11: 16-19 & John 8: 1-11).

'Friend of Sinners' is one of the 134 names and titles of Christ, in the Bible; but it is not a great one. The truly great titles and doctrines are: GOD; SAVIOUR;  LORD;  PROPHET;  PRIEST;  KING;  ADVOCATE and so on.
That may be true by textbook reckoning; but what about our personal reckoning? To us, 'Friend of Sinners' makes a lot of sense; and is more easily understood than such titles as ADVOCATE and MEDIATOR.
We may know something of what 'advocacy' means in principle, but few will have experienced its application in practice.
But friendship ... that's different! We all experience it; and we can raise our concept of friendship to the highest level that we can imagine, and say: 'The friendship of Jesus is like that: only more so’.
Who gave Jesus the title 'Friend of Sinners’? Apparently, his enemies did, and Jesus repeated it, to indicate their view of him. (Matthew 11: 16-19.).
Just as the term 'Methodists' was used, in a sneering way, to describe those who followed Wesley's methodical system of bible-study; prayer and fellowship; and was happily accepted by the very people sneered at…
... So with 'Friend of Sinners'. Jesus himself took the term aboard; and it became adopted into the Church's understanding of this aspect of God's mercy, love and grace in Christ.
'Friend of Sinners' is not one of the great titles of Christ, because it is far too open to possible misunderstanding and misuse. PROPHET; PRIEST; KING;  ADVOCATE; MEDIATOR and the like, cannot easily be misapplied: but FRIEND can become used lightly; or misused; allowing concepts of divine friendship, to degenerate into a sort of chumminess towards God.
The Church, being old and wise, doesn’t set the greatest value on the title; but, at the same time, recognizes the importance of it to those who do place proper value on concepts of friendship with the Lord.
One direct-from-Christ teaching about friendship with him, is found at a famous text in John 15, part of which says: ‘You are my friends if you do what I command you’...
... and, in our obedience toward Christ, as God, Saviour and Lord; there is no place at all for the slightest degree of a ‘chummy’ approach. However, the Church leaves it to the personal wisdom of each of its members, to take that title: 'Friend of Sinners', and to apply it both carefully and prayerfully.
Now let's look a bit more closely at the text, at John 8.1-11.
V.2. The 'temple courts' were a series of large, open-to-the-sky courtyards, each having covered walk-ways, around the inside of the high walls, much like the cloisters of our cathedrals.
In these covered walk-ways: the rabbis taught the scriptures, and gave their opinions in matters of Hebrew law. The text tells us that a lot of people followed Jesus into the temple courts, where 'he sat down to teach them'.
Sitting down to teach, and preach, was always the practice in those New Testament days; and, for centuries, the Christian Church did the same.
In these islands, the pulpit is a fairly modern invention. Preaching always used to be undertaken from the seated position. That is why almost all parish churches, and many other, denominational churches, have two chairs at the front, facing the congregation.
These symbolize the preaching and teaching chairs that were once used by Bishops and Archdeacons, when they visited churches, to take services and meetings. However: back to old Jewish practice.
Almost always, a teacher sat: with those being taught sitting at the same level. By so doing, they made something of a statement; that all were equal in the sight of God; and in their need to understand the scriptures, and to grow in spiritual knowledge.
Jesus, who never went against the best of Jewish practice, sat down to teach, putting himself at the same level with those who sat around him.
V.3. says: 'The teachers of the law, and the Pharisees, brought in a woman caught in adultery'. 'Brought in' means that they actually took her into the temple courtyards, and that was a very wrong thing to do.
It was wrong, because Jewish law said that no part of the temple should be used for anything other than study, prayer and worship; and here we find lawyers themselves breaking that law, for their own reasons.
They used the actual case against the woman, in order to help manufacture a case against Jesus. For their own wicked purposes, the men appointed to preserve the law, manipulated it instead.
It was wrong because the woman that they intended to kill was terrified and humiliated enough as it was; without being forced to stand in front of Jesus; and the crowd around him, who were sitting.
By forcing her to stand there, those men emphasized the difference between the good people sitting down, and the bad woman standing up.
V.3b - 5. states that: ‘They said to Jesus: "Teacher, this woman was caught in the very act of adultery. In the Law, Moses commanded us to stone such women. Now, what do you say”.
Whatever Jesus might say; they intended to kill her. However, for all their wicked scheming; they would not dare to profane the temple, by killing her within it. She would be taken just outside the great wall of the city; to where the rubbish-dumps were; and there they would stone her to death.
That's what they intended to do; but first, they wanted to catch Jesus out, if possible, so they asked him: ‘Now, what do you say?’ Jesus did not answer straight away.
V.7. tells us that ‘they kept on asking him questions’. Those men had contrived an opportunity to do mischief; and they weren't going to let it slip by, without taking full advantage of it.
When Jesus finally answered them; he did it in that wonderful way that he had, of taking hold of a situation, and directing its outcome, without actually breaking the law, or even appearing to do so.
He said: ‘If any of you is without sin, let him be the first to throw a stone at her’. I especially like the next part of the text: ‘At this, those who heard, began to go away, one at a time; the older ones going first’. Those 'older ones' had been around longer than the others, and had sinned more.
Our reading goes on to say that they went away: ‘ ... until only Jesus was left, with the woman still standing there'. Then comes a particularly lovely part of the story of Christ's mercy, love and grace.
V.10. of our N.I.V. bibles says: 'Jesus straightened up'; but the original Greek text renders it as: ‘Jesus stood erect’. And the point is this.
Up to that moment; the 'good' Christ was still seated; which position could have emphasized the difference between him and the 'bad’ woman, who was still standing.
However, just as he had sat on the same level as the, supposedly, ‘good' people, that he had been teaching; now Christ deliberately stood up, putting himself on the same level as the 'bad' woman, whom he was now helping.
Jesus - God's Messiah to a needy world - had tremendous compassion for all caught up in the ills of life; and he illustrates this in our text, by his wonderful gesture of acceptance; that gave the woman in question an unlooked-for hope, and a whole new beginning.
Jesus stood up, on a level with her, and asked: ‘Woman, where are they? Has no-one condemned you?’ to which she replied: ‘No-one, sir’. Then comes the best part of the entire event, as Jesus gave that woman her freedom, and a warning not to risk losing it again.
It wasn't the accusers walking off, and leaving the scene, that gave the woman her freedom; it was Christ himself - and this in two ways.
Without bending the law in the slightest, he challenged her accusers to fulfil it, in a particular manner: which they could not do. In shame and dishonour, they crept away; and they would never dare press that same charge against the woman again. But Jesus himself could have done so.
As a recognized rabbi, he could have invoked the Law; got a group of men together, and had her stoned to death. Instead, he waived all such rights, and began to demonstrate something of God's great, redemptive love, that would be fully shown at the cross; and remain in being for ever.
Christ confirmed the triumph of love over rights, by saying: ‘Then neither do I condemn you’. He went on to give her this warning: ‘Go, and leave your life of sin’. He spoke out of loving concern for her.
She had come within a whisker of being killed; but Jesus had rescued her from that dire situation; and he did not want her to risk getting into another one, losing, forever, what he had gained for her.
In the Tribunal of Heaven, when Christ speaks for us; none may speak against us. Therefore, to us, the title: 'Friend of Sinners' makes a lot of sense, being rooted in the need of a special 'some-one' to speak for us, when all else may appear to be negative at the very least; or actually against us.
But ... if Jesus Christ is to be that 'special Some-One', and speak for us; we must, first, recognize our need; and turn to him.   
The Bible teaches us that Christ, in his earthly ministries, did not condemn people; but offered them freedom from the legal consequences of their sins; through God’s new law of mercy, love and grace.
In the Tribunal of Heaven, Christ does not condemn; but awaits the moment when he can not only be our Advocate, but also our Friend.
However, if Christ is to be that 'Special Some-One', speaking to our need, we must, first, speak it out, through repentance, and by saying: ‘Lord, I need you! Christ, I need you!  Lord, I need you!’  Amen.