In the first article of this series we looked at the episode in Luke's Gospel in which Jesus dined with tax collectors. We saw that Jesus seemed to have no compunction at all about having social dealings with this outcast group, even though they were clearly involved in sinful activity. In fact, Jesus' very defense of His dealing with them was that He "[…] had come to call 'not the righteous, but sinners to repentance." He likens these 'sinners' to 'the sick'. They were spiritually sick and they were sinning, and yet Jesus engaged in a very intimate form of social association, eating at table with them. He benefited from the revenues which they got from sin, and yet He remained untainted by them.
Here is an incident in the Gospels which describes such an encounter:
…And there was a woman in the city who was a sinner; and when she learned that He was reclining at the table in the Pharisee's house, she brought an alabaster vial of perfume, and standing behind Him at His feet, weeping, she began to wet His feet with her tears, and kept wiping them with the hair of her head, and kissing His feet, and anointing them with the perfume. Now when the Pharisee who had invited Him saw this, he said to himself, "If this man were a prophet He would know who and what sort of person this woman is who is touching Him, that she is a sinner."
Luke 7:37-39 NAS
We see the familiar pattern: Jesus interacts freely with people who are genuinely sinful, not just outcasts. The description says she was a sinner, which suggests prostitution, but does not absolutely require it. But whatever her sin, it is her chief identity. Again, we see that Jesus is denounced for His willingness to associate with such people, and again, we see that the material benefit to him is not trivial:
The use of an alabaster jar of perfume by definition makes this a luxurious anointing. So the woman either is quite wealthy (seldom the case with first-century prostitutes) or is making an enormous sacrifice.
Blomberg, Craig L.. Contagious Holiness (New Studies in Biblical Theology) (p. 133). InterVarsity Press. Kindle Edition.
Therefore, this seems to suggest the same theory that the critics of Jesus used to criticize His willingness to accept material (food) support from tax-collectors: the idea that the sinfulness of the person who gains the wealth spread to the person who benefits from it. But Jesus acts as though that theory is wrong. His actions seem to imply quite a different relationship between purity and impurity in His kingdom:
Far from being corrupted by this woman or her scandalous actions, Jesus has imparted some of his holiness to her (whether first at an earlier encounter or simply on this occasion). Purity, rather than impurity, is what is being passed from the one person to the other, and this holiness involves the entire person, not in degrees or gradations as elsewhere in Judaism (Moritz 1996: 57).
Blomberg, Craig L.. Contagious Holiness (New Studies in Biblical Theology) (p. 137). InterVarsity Press. Kindle Edition.
I think it is important to see that these are not mere social encounters, like just standing near someone in a social setting. The ancient economy revolved around dining experiences and this is where much of wealth and business relationships centered. Jesus Himself acknowledges the interconnectedness of dining and commerce. Dining is a system of lending and advancement. Patrons fed their proteges. Dinners were 'repaid' (Jesus' word) which means exactly what the word implies: that dinners were payments. For those not traditionally employed, such as Jesus, such invitations were part of one's daily bread.
Here's Jesus on dining as a payment/repayment system:
And He also went on to say to the one who had invited Him, "When you give a luncheon or a dinner, do not invite your friends or your brothers or your relatives or rich neighbors, lest they also invite you in return, and repayment come to you. "But when you give a reception, invite the poor, the crippled, the lame, the blind, and you will be blessed, since they do not have the means to repay you; for you will be repaid at the resurrection of the righteous."
Luke 14:12-14 NAS
Clearly, Jesus taught that meals with associates were much more than mere social cues as they are in our day--they were in fact a form of economic activity. He takes that as a given, but shifts the focus towards being generous towards God. The idea is that He assumes that there will be repayment, but that God, rather than the noblemen, etc. plays the role of the patron. Feeding the poor and crippled is still a loan and still bears a yield, but now it is God who repays.
It is important to note that Jesus does not deny the sinful nature of the dinner partner. The tax gatherers are the 'sick' and the 'sinners'. The woman with the expensive vile of perfume is a 'sinful woman.' But He does, through His actions, deny the notion that their sinfulness travels to Him along with their material support. Jesus is there for a reason, not just for a free meal or for free perfume, but to save that which was lost, which means that He does engage with them, confronting in one form or another their sin:
"Jesus thus defies the conventions of his world by his intimate association with a group of people deemed traitorous and corrupt in his society. Still, he does not condone their sinful lifestyles but calls them to repentance, transformation and discipleship."
Blomberg, Craig L.. Contagious Holiness (New Studies in Biblical Theology) (p. 102). InterVarsity Press. Kindle Edition.
The woman clearly has been effectively reached, perhaps merely by Jesus' willingness to receive her. In spite of her reputation, there seemed to be no need for her to feel the burden of sin. It was the release of grace which led to what is clearly an act of devotion and a changed heart. Her income may have been ill-gotten, but it was not ill-given.