I was standing at a sink washing my hands in a public restroom where I had been several times before. I looked at myself in the mirror as I scrubbed my hands — I may have been wearing a pirate costume — and then I heard a voice. When I found the face in the mirror next to mine, I realized it was one of my daughter’s friends. I WAS IN THE WRONG BATHROOM. . . in a pirate costume. . . that poor girl. I was embarrassed. All I knew is that I didn’t belong. I had invaded a space that was not meant for me.
Have you ever been somewhere you didn’t belong? Where you felt out of place, not sure how to act or what to do?
We’re gonna read a story today about someone else who went where they didn’t belong.
This story is related to our last series in Ruth. I consider the woman in today’s story to be much like a New Testament Ruth — she goes into a place where she isn’t welcomed, where she doesn’t belong. But her brave surrender eventually brings redemption.
Turn with me to Luke 7:36-50. Luke is the 3rd book in the New Testament — about ¾ of the way through your Bible. If you don’t have a Bible, stop by our welcome center on your way out and let us give you one. For now, follow along on the screen.
Imagine with me for a moment. It’s first century Israel. You’ve been waiting for generations for the Messiah, the redeemer who will rescue us all, and you’re especially hoping for it now that the Romans have taken over. People are talking about some guy named Jesus who seems to be gaining traction — stories of healings, evil spirits driven out, even someone raised from the dead. People say he teaches with an authority like no one before him.
Then you get an invitation. Your friend Simon is a religious leader who’s heard the rumors too. Could Jesus actually be the Messiah? Simon has arranged a dinner with Him and invited you. Of course you’re not turning that down — you’ll be with everyone who matters in your community and finally get to meet this guy everyone is talking about.
Luke 7:36
36When one of the Pharisees invited Jesus to have dinner with him, he went to the Pharisee’s house and reclined at the table.
When it says they “reclined” — that’s literal. Guests rested on their left arms around a low table and ate with their right. They would have eaten barefoot, feet stretched out away from the table, because the host took sandals at the door.
Simon wanted the flex of having someone famous at his house. Dinners like this were served in open courtyards so people walking by could see. It was quite common for people to stand outside listening. Yes – specific people were invited — but there was an open door policy too.
Luke 7:37-38
A woman in that town who lived a sinful life learned that Jesus was eating at the Pharisee’s house, so she came there with an alabaster jar of perfume. 38As she stood behind him at his feet weeping, she began to wet his feet with her tears. Then she wiped them with her hair, kissed them and poured perfume on them.
There’s a lot to unpack here. First — “a woman who lived a sinful life.” Most scholars believe she was likely a prostitute. This is NOT a woman who should have been there. Just because a door is open doesn’t mean you belong. Right? I could walk into the women’s bathroom — but I didn’t belong.
There was no physical door keeping her out, but she wasn’t accepted. She knew her place. She knew how people saw her. She didn’t belong in Simon’s world. But she also knew something they didn’t. She understood that she DID belong with Jesus. The room said she didn’t belong. Jesus said otherwise. She believed Jesus. That knowledge is what moved her feet.
She felt every eye staring the moment she entered — and to approach Jesus . . . the respected rabbi, honored guest, as a woman? Man, that would have been unheard of. Jaws are on the floor.
She was probably terrified. She went anyway. That’s the whole sermon right there.
But she went anyway. Nobody stumbles into surrender. You have to decide to go.
Think about Ruth from our last series on the threshing floor — she and Naomi plotted and planned that encounter with Boaz.
Like Ruth, this woman made a deliberate decision.
Let’s talk about the jar, too. Women commonly wore a small sealed alabaster jar of perfume around their necks. To use it you had to break it open. This was likely her most prized possession — some scholars suggest it may have been the only thing she owned. Perfumes like this were used to anoint someone’s head, but she used it on Jesus’ feet. In humility, she recognized that even the best she had was only good enough for his feet.
As the bottle broke, so did she. Her tears spilled out. She didn’t try to fix herself up before coming to Jesus. She broke herself open knowing he would do the fixing. Our broken pieces can be made whole by Jesus. Although she didn’t belong there and people were staring, she was consumed. She lost herself in this moment. (maybe losing yourself in Jesus’ presence is exactly what we should do?) It was just she and Jesus. So much so that when she dried his feet, she used her hair. A woman’s hair was always covered — letting it down was considered immodest, and even more so given her past. The crowd would have been aghast. But she didn’t notice. She didn’t care. She saw Jesus and only Jesus. Nothing else mattered. SHE WENT ANYWAY.
And notice something else: she never says a word.
It doesn’t appear that she planned a speech, rehearsed an apology, or wanted to defend herself. No!
Her tears speak.
Her perfume speaks.
Her kisses speak.
Her hair speaks.
Sometimes surrender doesn’t need an explanation. It just needs to happen.
She hadn’t said anything. Simon, however, had plenty to say—even if he only said it to himself.
Luke 7:39-40a
When the Pharisee who had invited him saw this, he said to himself, “If this man were a prophet, he would know who is touching him and what kind of woman she is—that she is a sinner.”
40Jesus answered him, “Simon, I have something to tell you.”
The verse says, “he said it to himself” — not a word out loud, but it says, “Jesus answered him.” Jesus over here reading minds. Simon’s thought was “if he only knew what kind of woman. . .” and then Jesus answers his thoughts . . . Not only did Jesus know what kind of woman she was, he also knew what Simon was thinking. Jesus knew. He knew more than Simon could have imagined.
But why is Simon so concerned? In the Jewish world, this woman was considered unclean — and contact with her would make Jesus unclean too. No prophet would allow this. Simon thinks he’s figured it out. Jesus cannot be the Messiah, but he doesn’t understand that Our past doesn’t make Jesus unclean. His purity makes us clean.
Simon never wanted to risk his reputation or his standing in the Jewish community. He wanted to be close enough to check Jesus out but not close enough to be fully associated with him. Watching Jesus receive this unclean woman confirmed what he already wanted to believe. Simon wanted the prestige that came from knowing Jesus, but he wasn’t willing to give himself to him. He invited Him in, but held him at arm’s length. He thought His reputation was too much to lose if Jesus didn’t turn out to be the Messiah.
So Jesus tells him a story.
Luke 7:40-43
40Jesus answered him, “Simon, I have something to tell you.”
“Tell me, teacher,” he said.
41“Two people owed money to a certain moneylender. One owed him five hundred denarii, and the other fifty. 42Neither of them had the money to pay him back, so he forgave the debts of both. Now which of them will love him more?”
43Simon replied, “I suppose the one who had the bigger debt forgiven.”
“You have judged correctly,” Jesus said.
Instead of defending the woman, Jesus gets Simon to speak the redemptive words himself. A reluctant confession — but Simon knows the truth. He immediately understood the implications of Jesus’ story. He got the message.
The $50 man is Simon. The $500 woman is her. But here’s what Jesus is really saying — it doesn’t matter whether you owe $50 or $500 when you have nothing in your pocket. Both are equally broke. Neither can fix this. Only Jesus can pay the price and offer the redemption we need.
He is the “true and better” Boaz. Jesus alone is the ultimate redeemer. With Ruth, there were two possible redeemers, but Boaz is the only one who chose to do it. He was willing and able to redeem Ruth. Jesus however, is better. he is willing and able to redeem all of us – the world. And there is no other. No one can compare. Jesus alone was able to pay the price for our sin – death. Death was the price and not only is he able . . . He has also already done it. That’s what the cross is all about. Jesus is the “true and better” Boaz.
Notice the order here too: the debt was cancelled first, then love followed. Her love didn’t earn forgiveness. It was the fruit of it. She loved because Jesus forgave.
Luke 7:44-47
44Then he turned toward the woman and said to Simon, “Do you see this woman?
Of course he had seen her. She had interrupted his dinner. Embarrassed him. Ruined the evening in front of his guests. But Jesus wasn’t asking if Simon had seen her. He was asking if he had really seen her. Simon had only seen her past. Jesus something else—a daughter worth redeeming.
Jesus continued:
I came into your house. You did not give me any water for my feet, but she wet my feet with her tears and wiped them with her hair. 45You did not give me a kiss, but this woman, from the time I entered, has not stopped kissing my feet. 46You did not put oil on my head, but she has poured perfume on my feet. 47Therefore, I tell you, her many sins have been forgiven—as her great love has shown. But whoever has been forgiven little loves little.”
Simon and everyone else expected Jesus to reprimand her. They’re trying to decide what to do about her, but Jesus . . . Oh . . . those are great words, “But Jesus.” He just welcomes her. And to everyone’s surprise, Simon, the supposed host of the party, gets the hard words. Washing feet, a kiss of greeting, anointing the head — these were basic expectations for any host, but Simon was too busy protecting his reputation. . . watching to see if Jesus would slip up. She wasn’t even the host and she surpassed all of it. By anointing his feet, she not only recognized him as a guest, but as a “distinguished” guest.
If we’re honest, we’re all at least a little like Simon. We want Jesus close enough to be useful — close enough for comfort, forgiveness, and peace — but not so close that he starts rearranging our lives. We want His rescue without His rule, His comfort without His correction. We invite Him to our table, but we’re afraid of truly receiving Him. If we’re not careful, We can become consumers who want a Savior but aren’t interested in a Lord.
Simon kept Jesus at arm’s length and walked away from the most important dinner of his life with nothing. He got close enough to observe Jesus but never close enough to be changed by him. He didn’t think he needed grace . . . well, not much of it anyway. He thought she was the only one who needed grace. Simon opened his gate, but she opened her heart. Only one of them truly welcomed Jesus.
Simon knew facts ABOUT Jesus. This woman KNEW Jesus—trusted Jesus. That’s what we lose when we keep Him at arm’s length. Knowing Jesus. We forfeit knowing Jesus. How can you be intimate with someone you’re holding back?
What matters most isn’t the size of your sin. It’s the direction of your surrender. Simon stayed put. She went toward Jesus. She probably DID care what people thought. That’s what makes it brave. She felt the stares. She sensed the accusations, and knew the whispers, but she decided that Jesus was worth it.
Luke 7:48-50
48Then Jesus said to her, “Your sins are forgiven.”
49The other guests began to say among themselves, “Who is this who even forgives sins?”
50Jesus said to the woman, “Your faith has saved you; go in peace.”
A woman who had lived her whole life in sin. An outsider. Marginalized. Someone who just shocked an entire room. Even a woman like this can be forgiven.
You can be too. You’re not too far gone. Jesus didn’t show up at that dinner and leave empty-handed because of Simon. He came for everyone in that room — including the woman nobody else wanted there. Jesus is there for you too.
Some of you are like this woman — nothing to offer, nothing to lose. You might feel out of place just being here this morning. This kind of surrender seems risky, but I’m telling you, once you’ve done it, it feels like the only sane thing you’ve ever done. When you come to Him anyway, Jesus will receive you with open arms. Decide today. Go anyway.
Some of you are Simons. Life is pretty good. You’ve only got a $50 debt — or so you think. You come to church. You hang out with the right people. You feel like you have everything to offer and everything to lose if you really follow him. You know the answer is Jesus, but you also know you’ve been holding back. Managing your reputation is costing you the most valuable relationship you could ever know. It’s never going to feel like the right time. Bravery isn’t doing it without fear. It’s doing despite the fear. Go anyway.
Hear what Jesus said to her.
“Your sins are forgiven.”
“Your faith has saved you.”
“Go in peace.”
The Greek here is actually go “into” peace — not just something you carry, it’s also something you walk into. You don’t arrive at peace. It’s not a destination, but a journey. You walk into it — one surrender at a time, each time you step over that threshold in faith. Peace is a direction that shapes us more and more into the image of Jesus.
And that’s the hardest part: Yes, it’s hard to walk through the door and into that courtyard, but the hardest part isn’t the moment we bow down. It’s the staying down. The hardest part is our day-by-day, moment-by-moment continuous surrender – it’s the accumulation of a lifetime of faithful brave steps. Many have moments of surrender. Disciples learn to live there. The first step takes courage. The next thousand take surrender.
Wherever you are in your walk with Jesus, (Whether you’re like this woman or like Simon.) There is always more peace to step into. Always somewhere left to go.
Ruth crossed the threshold into Bethlehem.
She crossed onto the threshing floor.
This woman crossed the threshold into Simon’s courtyard, but that wasn’t the biggest threshold. She crossed from shame into forgiveness,
from outsider to daughter,
from condemnation to peace.
And both of these women found a redeemer on the other side.
What is the threshold waiting for you today?
Seriously, stop, pause and think about it a minute. Where do you need to be brave? To trust Jesus? What threshold do you need to cross?
Focus on Jesus. Forget the excuses. Ignore the stares. Go anyway.
Let’s pray:
Jesus, We come to you the same way she did — some of us terrified, some of us holding back, all of us needing the same thing she needed. A Redeemer. Thank you that you are exactly that. The true and better Redeemer — one whose purity doesn’t get stained by our dirt, but whose purity makes us clean. Lord, for those who came in today feeling like they don’t belong — like their past disqualifies them — remind them that you are not looking at them the way Simon looked at her. You see a person. You see someone worth redeeming. Give them the courage to stay down long enough to hear you say, “Your sins are forgiven. Go into peace.” And for those of us who are more like Simon — who have invited you to the table and kept you at arm’s length, who have wanted your rescue without your rule — convict us. Give us the grace to finally let you in. For all of us — remind us that peace is not just a destination. It’s also a direction. And there is always more of it to walk into. Lord, we understand that nobody stumbles into surrender. We have to decide to go. So today, Lord — help us decide to come to you—to go anyway. In the name of Jesus, who forgives, who saves, and who sends us into peace . . . AMEN.
