Unmasking Authenticity: Embracing Vulnerability with Jesus
Summary
Fear and shame are powerful forces that shape how we live, often working together to keep us from being our true selves. Like animals that camouflage to avoid danger, we too put on masks to blend in, to avoid rejection, and to protect ourselves from pain. These masks can take many forms: the athlete mask in the locker room, the relationship mask when we’re desperate not to be alone, or even the church mask when we want to appear perfect among other believers. Sometimes, we wear so many masks that we lose sight of who we really are, and the mask becomes our identity.
The story of Billy Tipton, a woman who lived as a man for decades just to play jazz music, shows how far we’ll go to avoid rejection and pursue acceptance. But the Bible gives us a different picture in Luke 7, where two people encounter Jesus: Simon the Pharisee, who wears the mask of religious perfection, and a woman known only by her reputation as a sinner. Simon hides behind his status, refusing to show Jesus the basic courtesies of hospitality, all to maintain his image before others. The woman, on the other hand, throws off her mask, running through her shame and fear to fall at Jesus’ feet, weeping and pouring out her most precious possession.
Jesus sees past the masks. He sees the pain, the longing, and the brokenness that others ignore. While Simon clings to his mask and leaves unchanged, the woman’s vulnerability leads to forgiveness, peace, and a new identity. The challenge is clear: the masks we wear may protect us from rejection, but they also keep us from the healing and transformation that only Jesus can give. True freedom comes when we risk being real, bringing our whole selves—shame, fear, and all—to the feet of Jesus.
The world tells us to hide, to pretend, to perform for acceptance. But Jesus invites us to take off the mask, to trust Him with our deepest wounds, and to discover that His love is greater than our fear of rejection. The question is not whether we have masks, but whether we’re willing to lay them down and let Jesus change us from the inside out.
Key Takeaways
- Fear and shame often work together to keep us from authenticity, driving us to put on different masks depending on our environment. These masks may help us avoid rejection in the short term, but they ultimately prevent us from experiencing genuine connection and transformation. The more we rely on them, the more we risk losing our true selves. [04:00]
- The story of Simon the Pharisee and the woman in Luke 7 reveals that religious performance and outward appearances can become just another mask. Simon’s need to maintain his image before others kept him from honoring Jesus and from showing compassion to the broken. When we prioritize reputation over relationship, we miss the opportunity for real encounter with God. [09:16]
- Jesus sees beyond our reputations and the labels others put on us. Where others saw only a sinner, Jesus saw a daughter—someone deeply wounded, longing to be loved, and courageous enough to come to Him. His response to our vulnerability is not condemnation, but forgiveness and peace. [16:43]
- The masks we wear can become so much a part of us that we forget who we are without them. Like Billy Tipton, we may live for years as someone we’re not, all for acceptance or success. But Jesus calls us to lay down the false identities and find our true selves in Him, even if it means facing our deepest fears. [21:28]
- True transformation happens when we run through our shame and fear to the feet of Jesus, refusing to let the opinions of others define us. The woman’s act of worship was costly and public, but it led to forgiveness and peace. The invitation is to take the risk of being real with God, trusting that His acceptance is worth more than any mask we could wear. [23:07]
Youtube Chapters
[00:00] - Welcome
[00:30] - Fear and Shame: The Tag Team
[02:10] - Camouflage and the Masks We Wear
[04:00] - The Athlete, Relationship, and Church Masks
[06:45] - The Story of Billy Tipton: A Life Behind a Mask
[09:16] - Simon the Pharisee: Religious Masks
[11:59] - The Scandalous Entrance: The Woman with a Reputation
[13:30] - The Woman’s Act of Vulnerability
[16:43] - Jesus Confronts Simon’s Thoughts
[17:21] - The Parable of the Two Debtors
[18:03] - Who Should Show Compassion?
[19:30] - The Cost of Keeping the Mask
[21:28] - Gilbert Chikli: Fraud and False Identity
[22:27] - The Difference Between Fraud and Surrender
[23:07] - The Invitation: Take Off the Mask
[23:57] - Prayer and Next Steps
Study Guide
Small Group Bible Study Guide: “Taking Off the Mask”
---
### Bible Reading
Luke 7:36-50
(Jesus is anointed by a sinful woman in the house of Simon the Pharisee)
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### Observation Questions
1. In the story from Luke 7, what are some ways Simon the Pharisee acted differently from the woman when Jesus came to his house?
[[09:16]]
2. What did the woman do with her perfume, and why was this act so shocking to everyone in the room?
[[11:59]]
3. How did Jesus respond to Simon’s thoughts about the woman, and what story did He tell to make His point?
[[16:43]]
4. According to the sermon, what are some of the “masks” people put on in different situations?
[[04:00]]
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### Interpretation Questions
1. Why do you think Simon, as a religious leader, chose to hide behind a mask of perfection instead of showing compassion to the woman?
[[09:16]]
2. What does Jesus’ reaction to the woman teach us about how He sees people who are hurting or have a bad reputation?
[[16:43]]
3. The woman risked a lot by coming to Jesus in front of everyone. What does her vulnerability show us about the kind of faith Jesus honors?
[[11:59]]
4. The sermon mentioned that sometimes our masks become our identity. Why is it so hard to take them off, even when we know they’re not who we really are?
[[21:28]]
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### Application Questions
1. The sermon talked about the “athlete mask,” “relationship mask,” and “church mask.” Which mask do you find yourself putting on most often, and in what situations? What are you afraid might happen if you took it off?
[[04:00]]
2. Think about a time when you hid your true self out of fear or shame. What did you miss out on by not being real in that moment?
[[04:00]]
3. Simon missed the chance to honor Jesus because he was worried about his image. Are there ways you’ve let your reputation or what others think keep you from doing what’s right or showing love?
[[09:16]]
4. The woman brought her shame and fear to Jesus and found forgiveness and peace. What would it look like for you to bring your “whole self”—even the parts you want to hide—to Jesus this week?
[[11:59]]
5. The world tells us to hide and pretend, but Jesus invites us to be real. What is one practical step you can take this week to be more authentic with God or with others?
[[23:07]]
6. The sermon ended by asking, “What are you going to do this week to take one of the masks off that you might be tempted to put on?” What is your next step?
[[23:57]]
7. If you saw someone else struggling under the weight of shame or fear, how could you help them feel safe enough to take off their mask?
[[18:03]]
---
Closing Prayer Suggestion:
Ask God to help you see yourself the way He sees you, to give you courage to take off your masks, and to trust Him with your fears and shame. Pray for each other to experience the freedom and peace that comes from being real with Jesus.
Devotional
Day 1: Masks of Fear and Shame Hide Our True Selves
Fear and shame often work together to push us into hiding who we really are, leading us to put on different masks in different situations to avoid rejection, loneliness, or pain. Like animals that camouflage themselves to escape danger, we too try to blend in—whether it’s the athlete mask in the locker room, the relationship mask to avoid being alone, or even the church mask to appear perfect. These masks may help us fit in temporarily, but they keep us from experiencing authentic relationships and the freedom that comes from being known and loved as we truly are. God invites us to step out from behind these masks and trust Him with our fears and shame, knowing that He sees and loves the real us. [04:00]
Psalm 34:4
I sought the Lord, and he answered me and delivered me from all my fears.
Reflection: What is one mask you tend to put on around certain people, and what would it look like to take it off and trust God with your fear of rejection today?
Day 2: Jesus Sees Beyond Reputation to the Heart
While people may judge us by our past or our reputation, Jesus looks deeper and sees our pain, our longing to be loved, and our true identity as God’s children. The woman in Luke 7, known only for her sin and brokenness, bravely entered a room full of judgmental eyes to pour out her heart at Jesus’ feet. Where others saw a “sinner,” Jesus saw a daughter—someone worthy of compassion, forgiveness, and restoration. No matter what others think or say, Jesus invites us to come to Him just as we are, without pretense, and receive His love and healing. [13:30]
Luke 7:36-38
One of the Pharisees asked him to eat with him, and he went into the Pharisee’s house and took his place at the table. And behold, a woman of the city, who was a sinner, when she learned that he was reclining at table in the Pharisee’s house, brought an alabaster flask of ointment, and standing behind him at his feet, weeping, she began to wet his feet with her tears and wiped them with the hair of her head and kissed his feet and anointed them with the ointment.
Reflection: Is there a part of your story or reputation that you feel disqualifies you from coming to Jesus? How can you bring that honestly to Him today?
Day 3: The Danger of Religious Masks and Hypocrisy
It’s possible to be close to Jesus in proximity but far from Him in heart if we’re more concerned with appearances than authenticity. Simon the Pharisee hosted Jesus in his home but withheld the basic courtesies of hospitality, all while maintaining a mask of religious superiority. His fear of what others would think kept him from showing compassion to the broken and from truly encountering Jesus. When we hide behind religious masks, we miss out on the transforming grace that comes from humility and honesty before God. [16:43]
Luke 7:39-47
Now when the Pharisee who had invited him saw this, he said to himself, “If this man were a prophet, he would have known who and what sort of woman this is who is touching him, for she is a sinner.” And Jesus answering said to him, “Simon, I have something to say to you.” And he answered, “Say it, Teacher.” “A certain moneylender had two debtors. One owed five hundred denarii, and the other fifty. When they could not pay, he cancelled the debt of both. Now which of them will love him more?” Simon answered, “The one, I suppose, for whom he cancelled the larger debt.” And he said to him, “You have judged rightly.” Then 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. You gave me no kiss, but from the time I came in she has not ceased to kiss my feet. You did not anoint my head with oil, but she has anointed my feet with ointment. Therefore I tell you, her sins, which are many, are forgiven—for she loved much. But he who is forgiven little, loves little.”
Reflection: In what ways are you tempted to hide behind a “church mask” or religious image? What would it look like to be more real with God and others this week?
Day 4: Running Through Shame and Fear to Jesus Brings Freedom
The woman’s act of worship was costly and courageous—she ran through her shame and fear, risking further rejection, to fall at Jesus’ feet and pour out her love. In doing so, she found forgiveness, peace, and a new identity, while Simon, who clung to his mask, left unchanged. True freedom comes when we stop letting shame and fear dictate our actions and instead run to Jesus with all that we are, trusting Him to receive us, forgive us, and make us whole. [18:03]
Hebrews 4:16
Let us then with confidence draw near to the throne of grace, that we may receive mercy and find grace to help in time of need.
Reflection: What is one area of shame or fear that you need to bring honestly to Jesus today, trusting Him to meet you with grace instead of rejection?
Day 5: Taking Off the Mask Leads to Life Change
Pretending to be someone we’re not—whether for acceptance, approval, or personal gain—ultimately leaves us empty and unchanged. But when we take off the mask and come to Jesus as we are, He meets us with love, forgiveness, and the power to live differently. The invitation is to stop living a fraudulent life for the sake of others’ opinions and instead follow Jesus wholeheartedly, letting Him define our worth and identity. This is the path to true transformation and peace. [23:07]
2 Corinthians 3:16-18
But when one turns to the Lord, the veil is removed. Now the Lord is the Spirit, and where the Spirit of the Lord is, there is freedom. And we all, with unveiled face, beholding the glory of the Lord, are being transformed into the same image from one degree of glory to another. For this comes from the Lord who is the Spirit.
Reflection: What is one practical step you can take this week to remove a mask you’ve been wearing and walk in the freedom Jesus offers?
Quotes
Simon walks out wearing the same mask he walked in. She walks out with Jesus saying, you've been saved. You have peace. I love you. Life changing. But she ran through the shame and the fear simply to be at Jesus' feet. Today's one last story. We're going to break into small groups and talk about fear. Some other things that you might talk about here from this message I think that might hit home. [00:21:01] (27 seconds)
Now Jesus had some harsh words to say to Pharisees all the time because Jesus saw them wearing masks. He said you're hypocrites. You say one thing. You act like you're perfect. You act like you've got all of the Old Testament law together. You have everyone convinced that you're so holy but I know who you really are. And you're as broken and messed up as everyone else. You're just pretending. And Jesus multiple times calls them out as hypocrites. But Jesus still talked to him. He still spoke with him. And he's invited to a meal at Simon the Pharisee's house. [00:10:02] (33 seconds)
But neither of them could repay him, so he kindly forgave them both, canceling their debts. Who do you suppose loved him more after that? And Simon answered, I suppose the one whom he canceled the larger debt. That's right, Jesus said. [00:17:28] (15 seconds)
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