The Pharisee probably didn't recognize her, he had moved out of her neighborhood a long time ago.
But was the Pharisee right? Jesus' feet were covered with the ointment, tears and hair of a prostitute. Don't condemn the Pharisee too quickly, we would have asked the same question. Even a prophet would not have accepted this behavior, but the Messiah? It seems like us Pharisees even have the weight of Scripture on our side. Isn't a good name better than riches? (Proverbs 22:1) To put it into today's jargon, wasn't Jesus hurting his "testimony"?
It's interesting that Jesus never answers the Pharisee's question. Jesus just tells a story about the magnitude of redemption with the response worshipping at his feet. Understand how incredible forgiveness is and you won't ask self-righteous questions. When we understand salvation, we're not surprised by the prostitutes actions--we're amazed the Pharisee didn't join her at Jesus' feet.
It's still important to answer the question. Wasn't the Son of God tainting his holy reputation? Why did He live the kind of life that people called Him, "A glutton and a drunkard, a friend of tax collectors and sinners"?(Luke 7:34) The answer is redemption. First, redemption gives us perfect righteousness in the eyes of God. God is perfectly pleased with His Son. Jesus wasn't preoccupied with what people thought of Him because He knew what His Father thought. God looks at us and sees Jesus. People can look at us and think whatever they want. Second, redemption illustrates the priority of seeking sinners. A good name is better than riches, but saving sinners is even better. Jesus' reputation is one more thing that He laid down so that we could experience the eternal weight of glory. He thought we were more important than His reputation. Third, redemption points us to eternity. Jesus allowed more than His reputation to be slaughtered. He hung naked bearing God's wrath in open shame. A jeering, blasphemous mob still surges around the cross enjoying their mockery. But Jesus will be vindicated. The crowd will shut its mouth and bow its knee. Jesus' marred body will be the ultimate object of the sweeping, thunderous song of eternal praise. A good name is better than riches, just not in this life.
Without redemption, "testimony" can be moralistic cowardice. Christ sacrificed His reputation for sinners, shouldn't we? Reflect the depth of redemption in the breadth of your ministry. Go out to eat with sinners. Find them where they are. Jesus did. Don't ruin your reputation with dumb things. If you tarnish your reputation with stupidity or sin, shame on you. But if pursuing sinners makes you look bad, you're in good company. The presence of a squeaky-clean reputation and the absence of redemptive relationships should tell us something's wrong.
