Notorious Former Sinners! Part 1: The Prostitute

by Paul Cypert

Luke, a follower of Jesus and later one who becomes an Apostle and author, records, in his Gospel account of the days in which Jesus was on this earth, stories of a prodigal son, the Pharisee named Simon and a prostitute who crashes Simon’s dinner party, and the story of a Publican (tax collector) and an unnamed Pharisee.

I find it fascinating that all three stories incorporate an antagonist whom, by all accounts, sees themselves in religious right standing with God and the world based on merit and status.
Luke’s stories unravel for us a perspective of how three separate individuals somehow saw themselves and their condition and responded.

All three found a moment of divine clarity; all three responded and found deep meaning springing forth from their actions.

 So, this story begins with Jesus being invited to an after hour dinner party hosted by one Simon, a Pharisee.

Pharisees were holy men who kept the law; pursued purity with a passion and wanted nothing more than to live lives that pleased God. They were sincere, albeit sincerely misguided.  And were enemies to those who saw life differently than they.

Simon’s invitation, most likely isn’t driven from a desire to hang out with Jesus but, in some way, to expose or entrap Him. To find something to use against Him.

Remember, these are the guys who eventually put a cross on Jesus’ back. Who then carried the wood that would kill to a hill outside a holy city.

Let’s pick up the dialogue, Luke chapter 7, verse 37:

“And there was a woman in the city who was a sinner”.

She practiced sin. That’s how she made her living. She was a prostitute and well known by Simon and the others at the dinner party; they knew exactly who she was, no need of an introduction.

She crashes the party. Small vials of perfume, necessaries for her trade, hung around her neck.
If you put the gospel accounts together, Jesus’ last message prior to the dinner party was Matthew 11,

“If you are weary and heavy laden, come to Me and I will give you rest for your souls for my yoke is easy and my burden is light.”

Perhaps, but most likely she heard this message.

Tired, wearied, broken, guilt-ridden, living outside of normal life. There she stood, in the house of someone who was directly the opposite of everything she was, a notorious prostitute who was about to demonstrate for all, with pristine clarity, that she was now a believer in the young Messiah.

Ready for some burden free living.

She now acts in a manner that many call salacious, but I call worship.

Weeping, she falls at Jesus feet and her tears of joy became the water necessary to cleanse those feet, she kisses those feet, and not having a towel she let her hair down and dried those beautiful feet, then perfumes those feet.

I’m telling you the tension level in that room was intense.

Simon in his thoughts says,

“if he were a prophet he would know who this woman truly is”.

Jesus knew Simon’s thoughts and tells him a parable.

It’s pretty simple; one guy owes someone a couple of days pay and the other guy a couple of years pay. Both debts are forgiven.

Question? Which guy was most appreciative?

And this a major hedge by Simon,

‘I suppose the one with larger indebtedness’.

Well you supposed right, Simon the Pharisee!

For Jesus says,

“He who is forgiven much loves much”.

If you think Jesus is a mild-mannered, peace-loving, long haired, marginalized Hebrew, well, you’re wrong!

He, who intended to expose, now experiences a reversal of intentions and gets himself exposed!

Let’s read on…

Luke 7:44-47
44 Turning toward the woman, He said to Simon, “Do you see this woman? I entered your house; you gave Me no water for My feet, but she has wet My feet with her tears and wiped them with her hair.
45 You gave Me no kiss; but she, since the time I came in, has not ceased to kiss My feet.
46 You did not anoint My head with oil, but she anointed My feet with perfume.
47 For this reason I say to you, her sins, which are many, have been forgiven, for she loved much; but he who is forgiven little, loves little.”


In that culture, kissing was a big deal, and kissing indicated levels of status and interaction.
-A kiss of greeting on the cheek meant we are equals.
-Your teacher, clergy or rabbi was greeted with a kiss on the hand.
– An honored guest at a dinner party would have been embraced and kissed on both cheeks.
–Only slaves were required to kiss the feet of another human being, their masters.


So, kissing was a big deal for them but not so big with me, especially in a world laden with fear over the Covid-19 virus and a general discomfort with that kind of thing in general. It was also customary to put a little drop of essential oils on the forehead of your guest in order to enhance the dining experience. Food just tastes better when things smell better. Water was provided and sometime servants to wash the feet of guests.

Don’t you love verse 44?

Simon do you see this woman?

Of course, Simon saw her! Everybody there was seeing this woman and majorly uncomfortable about her presence.

And Simon, as your invited guest, everything you should have done as my host she did. Washed my feet, kissed me, anointed me with oil.

The woman’s act by no means was salacious; it was in some ways the right thing to do.
In another way, it was sheer abandonment; she joyously expressed with tears, possessions (perfume), took the posture of a slave (a bond servant) at His feet and worshiped, because she who is forgiven much loveth much.

Well, does it take all that?

Yea for some folks!

Well does it have to be that public?

Yea for some folks!

We pretty much should focus on not being an antagonist, you know, like Simon, a Pharisee.


Jason Huckabee

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