Jesus never had much to work with in terms of PR. Still doesn’t.
The logical thing to do if you want to attract people to your cause is find prospects who live out your ideals to represent you. What you don’t do is send people out to speak on your behalf whose lives discredit your cause.
As it turns out, God wants His grace on display through unlikely prospects.
Take the account of Jesus speaking to the Samaritan woman at a well as a prime example. She had lived with five men and was currently with her 6th.  By modern standards, that’s enough to get you quite the reputation – let alone how that was perceived in the ancient world. She was a complete outcast and by social standards, the worst possible prospect for Jesus to invest His time with. The disciples were shocked Jesus even bothered talking to her. Shouldn’t He be spending His time and extending His grace to good prospects … people who were more like them???
What we discover throughout all of scripture is that sinful, unlikely prospects are all that God ever had to choose from. That’s still the case. All of us by God’s standards are exactly like that Samaritan woman – undeserving of God’s grace. Sure, we might not be on our 6th common-law relationship, but pick your poison – we all sin.
Good news. God extends His grace to unlikely prospects.
Jesus shared His gospel with that Samaritan outcast. He’s the one who had come to take away her sin. She believed Him and in doing so, the sin that once defined and shamed her no longer had any power over her. She went around sharing how Jesus knew “everything that she ever did”. If the person you’re living with is your 6th, you don’t run around your small town telling everyone that Jesus knew about the previous 5 and has forgiven you for all of it. Your small town already knows all your business and are judging you for it. It’s self deprecating.
She’s been liberated. She’s free. Her sin no longer defines her. In fact, it’s become a testimony of God’s saving grace. Many Samaritans in the village came to faith in Christ because in listening to her speak, it was clear that a very unlikely prospect had come in contact with the One whose grace stretched further than her sin.
It still does.
 John 4:1-42