“At this point His disciples came, and they were amazed that He had been speaking with a woman” (John 4:27, NASB).
It was strange that Jesus spoke with the Samaritan woman at the well. The woman herself was surprised, as indicated by her question, “How is it that you, a Jew, ask for a drink from me, a woman of Samaria?” (John 4:9) The apostle John adds that the Jews and Samaritans did not have any dealings with each other. Also, –and the woman didn’t say this, but Jesus knew– the Samaritan woman didn’t have a good reputation. She went from man to man (John 4:18). Finally, the mere fact that Jesus was talking to a woman (which was considered a waste of time for a rabbi at that time) astonished the disciples.
However, “no one said, ‘What do you seek?’ or, ‘Why are you talking with her?'” (John 4:27) because, apparently, they were already accustomed to this habit of Jesus. He spent time with outcast people.
For example, the inspired writer Mark relates in his Gospel that Jesus could be seen eating and drinking with publicans and sinners. On one occasion, while observing him, the scribes and the Pharisees asked, “Why does he eat with tax collectors and sinners?” (Mark 2:16)
The problem with these religious teachers is that they came to certain conclusions based on what they could see with their own eyes. In contrast, Jesus knows the hearts of men (John 2:24-25). He comes to conclusions based not on our appearance, but on our reality; not on what we are now, but on what we can become.
With whom do we spend time? To whom do we preach? We should prefer, like Jesus, to spend time with sinners who recognize that they are sick and are willing to receive spiritual help. The problem is that this is not as pleasant as preaching to those who already appear to be righteous. But let’s remember that Jesus rejected the young ruler, the rich man, and the man who appeared to be righteous, and accepted instead the blind beggar who shouted his name and cried out for his help (Mark 10).