How to Be a Great Lover

Luke 7:36-50

February 10, 1991 | Ray Pritchard

My text today is one of the great short stories of the Bible. Somebody like Steven Bochco could turn this into a terrific one-hour drama on TV. You might call it “The Churchman and the Prostitute,” or you could call it “Guess Who’s Coming to Dinner?” It helps to have a sense of humor when you read this story.

It also helps to have two bits of background information: The first is that this story takes place at a formal dinner party in ancient Palestine. That’s important to know because in those days formal dinner parties often took place in an open courtyard. They were public events in that the neighbors felt free to come into the courtyard to observe the dinner party as it took place. They weren’t considered guests, but they weren’t intruders either. They were self-invited observers.

The second bit of information is that it was customary for the host to greet his invited guests with three things: 1. A kiss of welcome 2. Water for his feet 3. Oil to anoint his head.

This story is really a drama in five acts. I invite you to go with me to the El Shaddai Dinner Theater in ancient Hebron for the premier performance of “Guess Who’s Coming to Dinner?” Just as we find our seats the curtain rises on …


As we gaze at the stage we see a low table set in the middle of the courtyard. It is U-shaped with couches arranged so that the guests will recline with their legs facing outward.

Immediately we are introduced to the man who will be the central character … Simon the Pharisee. What a surprise! This man has invited Jesus to come to his house for supper. It’s a surprise because most of the time Jesus didn’t get along too well with the Pharisees.

But Simon was different. He was a Pharisee but not a very good one. He wasn’t deeply involved in anything. He was broadminded enough to invite this upstart young rabbi from Nazareth to dinner. No doubt he reasoned that it wouldn’t do him any harm. After all, it takes all kinds to make a world. Simon liked to be around influential people, it made him feel good to rub shoulders with the movers and shakers.

Not that he was committed to Jesus or his mission. Oh no, not at all. This was a social invitation, that’s all. He didn’t necessarily agree with all that harsh talk about the robbing of widow’s houses and whitened tombs. That was a little extreme for his tastes.

This was just a casual meal, the kind where you keep the good china locked up. Low-key, no big deal. That way he wouldn’t risk offending his more orthodox friends.

What words would you use to describe Simon? Urbane … polished … smooth … adaptable. He is a curious bystander in the game of life. He is diplomatic to a fault and likes to play it close to the vest. Above all, Simon is no fanatic. He is a man of the world. He thinks of himself as a man who never gets backed into a corner.

He fits well into the office … or the halls of congress … or the church. He would do well in Rome or New York or Chicago. He’s a classic middle-of-the-road man.

So it happens that Jesus has come this day to the house of a Pharisee for dinner. All is going well as the curtain falls on Act 1.


As the curtain rises, from stage left an unidentified woman enters. She walks around the table and stops at the sofa where Jesus is reclining.

The Bible is very discreet in calling her “a woman who was a sinner.” This woman was a prostitute. She made her living by selling her body to men. She was a professional and I have no reason to doubt that she was good at what she did.

The shock is that she would come to the house of a Pharisee. In ordinary times Simon and this woman would never meet. He would not go near a woman like her; she would not go near a man like him. They are from opposite ends of the spectrum. Yet strangely, they are thrown together for the same purpose. They both want to meet Jesus.

The center of attention now becomes this woman of the street. I do not know much about prostitutes, but of this much I am sure. A woman like that is a good judge of men. She sees them as they are. She has heard every promise, every come-on, every cover-up. She’s seen it all.

She knew Jesus was not like all those other men. He was not going to use her and throw her away. She heard in his words the promise of a way out of her ugly, empty life.

Simon watches, unbelieving, as this woman does something strange.

1. She intends to anoint Jesus’ feet with expensive perfume.

2. But she begins to cry and can’t stop.

3. As she cries, her tears fall on Jesus’ feet.

4. She dries his feet with her hair.

5. Then she smothers his feet with kisses.

6. Finally, she anoints his feet with the perfume.

If this seems odd, may I ask you to remember her background. She is used to touching men. She is not ashamed to show her emotions. She reacts to Jesus exactly as a woman with her background would react. It’s the only way she knows.

How would you describe her? Generous … affectionate … impulsive … demonstrative … emotional … passionate … uninhibited.

Why is she weeping? She loves Jesus and she isn’t afraid to show it.

She stands … . to honor his greatness

She weeps … . overwhelmed with sorrow over her past

She wipes Jesus’ feet with her hair … . a sign of deep humility

She kisses his feet … . a gesture of affection and respect

She anoints his feet … in gratitude for what he has done for her.

As Act 2 comes to a close, the scene shifts back to Simon who silently watches this shocking, sensual scene. He’s never seen anything like it! It goes against all his conservative instincts. He is deeply offended by what this woman has done.

A fallen woman caresses Jesus and it bothered him. He would never let a woman like that touch him. The whole thing was disgusting … revolting … dirty.

As the curtain falls, Simon ponders what he has just seen.


Jesus knew exactly what Simon was thinking so he told him a little story. It went like this. Once there were two men who owed money to a moneylender. One owed the man $5,000 and the other owed him $50,000. Neither one had any money so the lender, out of the goodness of his heart, canceled the debts. Nice simple story.

Then Jesus asked Simon the $64,000 question: Which of those two men will love the lender more? Simon smells a trap so he’s a little cautious in his answer. “I suppose the one who had the bigger debt canceled.” Jesus said, “That’s right.”

What does it mean? In Simon’s eyes, the prostitute was like the man who owed $50,000. Her debt to God was enormous because in Simon’s eyes she was an enormous sinner. Compared to her, Simon’s debt seemed to him like maybe $5.

But that’s not the point. If you can’t pay a debt, it doesn’t matter how much you owe. If you’re broke, you’re broke. In that sense, there is no difference between owing a little and owing a lot, especially if you don’t have any money.

The truth slowly begins to seep in. “Simon, we’re all in debt to God. Some owe more, some less. But none of us can pay even a penny of what we owe. Here is the gospel message: God is willing to forgive all debtors equally, the people who owe a lot and the people who owe a little!”

Simon is now at center stage and he is beginning to sweat. What Jesus means is painfully clear: “Simon, there is fundamentally no difference between you and the prostitute.”

As the message sinks in, the curtain falls on Act 3.


As the curtain rises, Jesus turns to the woman for the first time. But he does not speak to her. “Simon, do you see this woman?” What he means is, “Simon, do you know why she is doing these things?” Simon thought he did … but he didn’t.

Then Jesus systematically exposes the shabby treatment he had received. “You gave me no water, but she wet my feet with her tears. You gave me no kiss but she can’t stop smothering my feet with kisses. You didn’t even offer me cheap olive oil but she anointed my feet with expensive oil.”

“You kept me at arms length, but she was not ashamed of me. You didn’t even bother to show me minimal courtesy, but she lavished her love on me. You know religion, the Temple, the sacrifices and the Law. She knows none of that. You missed the whole point. She got it.”

What was Simon’s problem? HE THOUGHT HE WAS BETTER THAN THE PROSTITUTE. Simon said, “She is a sinner.” Jesus said, “No, she was a sinner.” God changed the tenses in her life.”

“Simon, your problem is that you see her as she was and not as she is. You think you see her but you don’t. For years, you knew her one way … but now she’s clean … and you can’t handle it.”

That leads me to this statement: A man who is never deeply committed to anything cannot understand somebody who is transformed by Jesus Christ.

Just before the curtain falls, Jesus speaks again. “Therefore, I tell you, her many sins have been forgiven–for she loved much. But he who has been forgiven little loves little.” That doesn’t mean what you might think. Jesus is not saying, “The worse you are, the more you are forgiven.” He is saying, “The greater you sense your own need for forgiveness, the greater will be your love when you are forgiven.”

You will have gratitude and love in exact proportion with your sense of your own sinfulness.

–If you think you have been greatly forgiven, you will greatly love God.

–If you think you have only been forgiven a little, you will only love God a little.

Jesus is boring in on Simon. He’s starting to fidget. He doesn’t like to get backed into a corner like this.

Our little drama is almost over. One act remains.


As the curtain rises, Jesus speaks to the woman for the first time. He says three things to her:

1. “Your sins are forgiven.” That takes care of her past.

2. “Your faith has saved you.” That takes care of her present.

3. “Go in peace.” That takes care of her future.

That’s all. He never says, “Don’t sell your body.” He doesn’t have to. She’s been set free.

What about Simon? He got more in this dinner party than he bargained for. More than he wanted. He planned a casual affair and it blew up in his face.

As the curtain falls for the final time, we see Simon staring at Jesus, a look of fear and amazement on his face.


As you walk out of the El Shaddai Dinner Theater, you wonder, “Just who is this little story all about?” Simon? The Prostitute? Jesus? Simon, the man who would not commit himself to anything. The woman who risked everything. Jesus who welcomed her and would have welcomed him.

Simon’s problem was not that he couldn’t see the woman. It wasn’t that he couldn’t see Jesus. Simon’s problem was that he couldn’t see himself.

Simon said, “I owe him nothing.” So he risked nothing. The woman said, “I owe him everything.” So she risked everything.

It’s strange, isn’t it, that the worst sinners often make the best saints. Why? Because flagrant sinners are more likely to discover that they are sinners.

Here is the abiding truth from this story: Your love for the Lord is directly related to your estimate of how greatly you have sinned and how much he has forgiven you. It’s not how much you sin, but how deeply you feel it that matters.

In truth, we’re all like that woman–so guilty we could never pay the debt we owe. Now we’ve been forgiven more than our minds can comprehend.

In truth, there’s a little Simon in all of us. We secretly think we’re better than we really are. So we hold back, play it safe, and never get radical in our commitment to Jesus Christ. Frankly, that’s why we have a hard time understanding those who do get radical.


This is a great story to read on the Sunday before Valentine’s Day. Simon represents so many men I know who have a hard time expressing their feelings. They keep it all on the inside because it’s safer that way. This week Time magazine (2/11/91, p. 72) carried an interview with Robert McNamara, who served as Secretary of Defense under Presidents Kennedy and Johnson. At the end, the writer asks, “Who is the real Robert McNamara?” Answer: “Very few people know.” Question: “Who knows?” Answer: “Well, Marge knew, my wife knew.” Question: “Who else? President Johnson?” Answer: “No, I don’t think so. No, people don’t know. People don’t know.”

Question: “Your kids?” Answer: “People don’t know, and probably not my kids. And let me tell you that’s a weakness. If you’re not known emotionally to people, it means you haven’t communicated fully to people. I know it’s a weakness of mine. But I’m not about to change now.”

Simon would understand exactly. “It’s a weakness. But I’m not about to change now.”

But if love is ever going to enter your life, you’re going to have to open your heart and show people how you really feel. It’s risky, it’s dangerous, but it’s the only way. If you stay like Simon, you’ll be safe, but love will forever pass you by.

No one ever said it better than C. S. Lewis:

To love at all is to be vulnerable. Love anything, and your heart will certainly be wrung and possibly be broken. If you want to make sure of keeping it intact, you must give your heart to no one, not even to an animal. Wrap it carefully round with hobbies and little luxuries; avoid all entanglements; lock it up safe in the casket or coffin of your selfishness. But in that casket–safe, dark, motionless, airless–it will change. It will not be broken; it will become unbreakable, impenetrable, irredeemable. The only place outside Heaven where you can be perfectly safe from all the dangers of love is Hell. (From The Four Loves, p. 169. Cited by Chuck Swindoll, The Quest for Character, pp. 113-114)

Love is risky business. You always have to take a chance, don’t you? If you’re going to say, “I love you” or if you’re going to send one of those cards that says “Be My Valentine,” you’re going to have to open your heart and let people see how you really feel. That’s scary, but there’s no other way.

Somewhere I ran across this statement that could have been written about our story: “I feel that God would sooner we did wrong in loving than never love for fear we should do wrong.”

As strange as it might seem, this story presents us with a clear choice. We can be like Simon or we can be like the prostitute. Think about that. By long years of religious training, most of us feel much more comfortable being like Simon. Luke included this story so that we would be challenged to become more like the repentant prostitute. The fact that we feel uncomfortable with that says a lot more about us than it does about the Bible.


After I preached this sermon in the first service, a friend came up and stuck a poem in my pocket. She said it had been a tremendous encouragement to go ahead and take the risky step of saying, “I love you.”

Turn, O Lord, my fears around.

Let them become a positive force

For good in my life

Until I … .

Fear not that I might fail

But fear rather that

I might never dare to

Discover my potential.

Fear not that I might be hurt.

But fear rather that I

Might never experience

Growing pains.

Fear not that I might

Live and lose.

But rather that I

Might never love at all.

What a great prayer. Either we live in our fears, captive to the past and what might happen in the future. Or we turn them around and by faith go forward with God.

We can choose to be with Simon and play it safe. In the end we will be sorry. Or we can be like that woman who smothered Jesus’ feet with kisses. It’s risky … and daring … and the people who see us may not understand. But at least they’ll know we really love Him.

Do you have any thoughts or questions about this post?