Gracefully Truthful

Digging Deeper Days

Finding the original intent of Scripture and making good application to our everyday lives as we become equipped to correctly handle the Word of Truth!

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The Questions

1) What does it mean to be a sinful woman? (verse 37)


2) What are the differences between the sinful woman and Simon the Pharisee? (verse 39-40)


3) What is the relationship between forgiveness and love?

Luke 7:36-50

36 Then one of the Pharisees invited him to eat with him. He entered the Pharisee’s house and reclined at the table. 37 And a woman in the town who was a sinner found out that Jesus was reclining at the table in the Pharisee’s house. She brought an alabaster jar of perfume 38 and stood behind him at his feet, weeping, and began to wash his feet with her tears. She wiped his feet with her hair, kissing them and anointing them with the perfume.

39 When the Pharisee who had invited him saw this, he said to himself, “This man, if he were a prophet, would know who and what kind of woman this is who is touching him—she’s a sinner!”

40 Jesus replied to him, “Simon, I have something to say to you.”
He said, “Say it, teacher.”
41 “A creditor had two debtors. One owed five hundred denarii, and the other fifty. 42 Since they could not pay it back, he graciously forgave them both. So, which of them will love him more?”

43 Simon answered, “I suppose the one he forgave more.”
“You have judged correctly,” he told him. 44 Turning to 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, with her tears, has washed my feet and wiped them with her hair. 45 You gave me no kiss, but she hasn’t stopped kissing my feet since I came in. 46 You didn’t anoint my head with olive oil, but she has anointed my feet with perfume. 47 Therefore I tell you, her many sins have been forgiven; that’s why she loved much. But the one who is forgiven little, loves little.” 48 Then he said to her, “Your sins are forgiven.”

49 Those who were at the table with him began to say among themselves, “Who is this man who even forgives sins?”
50 And he said to the woman, “Your faith has saved you. Go in peace.”

Original Intent

1) What does it mean to be a sinful woman? (verse 37)

In this passage, the woman is introduced to us as “a woman who was a sinner”. Her sin defined her. She was known for her sin. It was her identity. In the Greek, the word “sinful” means pervaded by sin. A sinful woman may have been one who prostituted herself, possibly because she was widowed, or had no other means of making an income. She knew her community identified her by her specific sin, and she would have been filled with shame as she was constantly distanced, unwelcomed, and the center of gossip. The inner thoughts of Simon the Pharisee reveal the attitude people took towards her because of her sin. Simon is revolted by the reality that Jesus would allow her to touch Him. He uses this fact to discredit Jesus’ status. A sinful woman was meant to be rejected, not embraced and drawn near. When we think of identity, it is the very essence of what we believe about ourselves. Our identity consists of what we think, or feel, make up the deepest truths about ourselves. Yet, Scripture teaches us we are all sinners. (Romans 3:23) We are even reminded we were “slaves to sin”. (Romans 6:6-22)


2) What are the differences between the sinful woman and Simon the Pharisee? (verse 39-40)

Jesus clearly lays out the truth here as He contrasts Simon’s cold reception to the effusive love of the sinful woman. (Luke 7:44-46) Simon didn’t wash Jesus’ feet, as was customary, neither did he greet Jesus with a kiss, which was the traditional manner of a host welcoming someone he respected. Additionally, Simon didn’t anoint Jesus’ head with oil, a common practice of hosts to show honor to a guest. In contrast, the sinful woman wept and washed Jesus’ feet with her own tears, wiped His feet with her hair, and bought special oil at great price to herself and poured it out on Him as an offering. These are outward differences, but Jesus goes on to show how these actions reflected both the heart of Simon and the woman. Inwardly, Simon didn’t perceive himself as needing Jesus’ forgiveness. He didn’t perceive his own sin and didn’t acknowledge Jesus as his Savior. In stark contrast, the “sinful woman” stepped into an extremely uncomfortable situation, bypassing her own shame to lavish Jesus with honor and gratitude. She did this because she knew her own depravity, while also acknowledging the immeasurable gift of Jesus’ forgiveness.


3) What is the relationship between forgiveness and love?

Special attention is required so we don’t turn Jesus’ message upside down. As we look at the actions of the sinful woman, and hear Jesus explain how her sins are forgiven, we might be tempted to think He forgave her because she poured herself out. We need to remember all sins are forgiven based on the love of God, not the love of man (or woman). We did not choose God, He has chosen to come to us! (1 John 4:19) Jesus laid down His life for all people while we were His enemies. (Romans 5:10) The forgiveness He extended cannot be earned, and no one can add to it through actions. In the parable Jesus told Simon, both people were forgiven. The cross is for all sin for all time. (Romans 10:12) It is available freely to all (Romans 10:13), but in order to actually be forgiven, we must intentionally choose to receive it. When a person like this sinful woman becomes aware of the debt they owe to God because of their sin, and then finds themselves completely freed of the debt by turning to Jesus, the love they feel in response is overwhelming. To the extent that a person acknowledges their sin debt to God, they will feel that much more overwhelmed by the canceling of their indebtedness. Surely Simon owed Jesus a deep debt. The trouble was he was unaware of his own need. In contrast, this woman knew. She had been freed from an identity shackled to sin and shame and given new life and unconditional love in exchange. This new life changed her identity forever and love overflowed without measure!

Everyday Application

1) What does it mean to be a sinful woman? (verse 37)

When we consider the status of the sinful woman in this passage, it is easy to separate ourselves from her. We might look upon her as lower than us (as Simon did). We may think there are sinners who do “small” sins and those who do “great” sins. We then mistakenly feel those with “greater sin” are beneath us. On the other hand, those who have walked with Jesus since childhood and haven’t led a debauched life may feel they never could muster this kind of gratitude and responsive love for Jesus. We need to understand that the love extolled in this true story is a love born of recognizing our own slavery to sin. Not one of us is better than another because sin, all sin, has equalized us before the throne of God. As we understand our own sinfulness, we begin realizing how great the sacrifice was, the humble, willing sacrifice, Jesus made to forgive us and draw us near. When we acknowledge our deep need, our real shame, and our enslavement to sin, we can thank God for His grand rescue with a depth we would not have otherwise reached. A love bubbles up within us when we see the completely voluntary and pursuant love of God for us completely not based on what we could do for God, rather rooted in the reality that He loves us fully, even in our sin.


2) What are the differences between the sinful woman and Simon the Pharisee? (verse 39-40)

The key difference between these two is an issue of pride. The pharisee saw himself as one who could judge Jesus and deny Him honor. He invited Jesus as a peer, but then failed to show any common signs of respect. In his heart, he didn’t see himself as needing forgiveness or having a life of sin. He defined sin as something blatant and external, with no regard for the internal heart condition. The woman knew herself to be a sinner, both outwardly and inwardly. Her sin defined her. She knew she was stuck and lived the life of an outcast. Interestingly, Simon’s sin, the sin of pride, is one Jesus spoke against frequently in His teachings. (reference examples) Whenever we see Jesus addressing someone who is stealing, cheating, or fornicating, we find Him inviting them to repentance and speaking forgiveness over them. When we see Jesus addressing pride, He often uses the words “woe to you.” (Matthew 23:13-29) Pride is a subtle, but powerful sin, effectively separating us from our sense of dependence and need. When we step into pride, we feel we don’t need God, His love, or His forgiveness. We are far better off acknowledging our sin and throwing ourselves at Jesus’ feet than standing back judging others and foolishly rejecting the love of God.


3) What is the relationship between forgiveness and love?

Jesus said, “her many sins have been forgiven; that’s why she loved much.” (Luke 7:47) It truly is that simple. The love we show is first and foremost responsive love to Jesus. Recently, I had an experience of procrastinating. I knew I should be getting something done, but I kept putting it off. It was more than an oversight. I was intentionally neglecting a responsibility. I noticed I wanted to stay away from my quiet time with Jesus because I was embarrassed for my irresponsibility. I went into prayer anyway. In that private time, Jesus approached me. I sensed Him saying, “I love you anyway.” There isn’t a way to convey the feeling or reaction I had, except to use the word freedom. I felt empowered, not shamed, just as Jesus had said to the woman caught in adultery, “Go and sin no more.” (John 8:11) I wanted to make things right, to respond to His sweet, unconditional love by doing what needed to get done. I was motivated by love to honor my Lord, not by fear to finish a checklist for my performance. When we love Jesus responsively, He changes our heart to deeply desire to do what is right. We don’t do it to earn His love, but as a thank you for His goodness towards us. We also love others well, without deep effort, because we have been filled with His love.

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Digging Deeper is for Everyone!

1) Take this passage (or any other passage).
2) Read it, and the verses around it,
several times
3) Write down your questions
as you think of them.
4) Ask specific culture related questions and be ready to dig around for your answers. Google them, use, or look them up in a study Bible and read the footnotes (click on the little letters next to a word and it will show you
other related verses!). (
5) Check your applications with other trusted Christians that you are in community with and embrace the fullness of God
in your everyday!

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Why Dig Deeper?

Finding the original meaning is a huge deal when we study Scripture and can make all the difference in our understanding as we apply God’s truths to our everyday lives.

In our modern-day relationships, we want people to understand our original intention as we communicate; how much more so between God and humanity?!

Here’s a little bit more on why we take Digging Deeper so seriously.

Study Tools

We love getting help while we study and is one of many excellent resources, providing the original Hebrew (Old Testament) or Greek (New Testament) with an English translation.

Want to know more about a specific word in a verse? Click on “Strong’s Interlinear Bible” then click the word you’d like to study. Discover “origin”, “definition” and hear the original pronunciation – That Is Awesome!

Want more background? Click “Study Tools”, then pick a few commentaries to read their scholarly approach, keeping in mind that just because a commentary says it, doesn’t mean it’s true. (just like the internet :-))

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