The time when Jesus spoke to the Samaritan Woman at the well, described in John 4: 1-42, is one of the most significant acts of evangelism in the Gospels. The Samaritan Woman, being of her background, was not someone who a Jew such as Jesus would speak to at all, so Jesus’s choice to speak to her was puzzling to her. It also turns out that she had been married five times and lived with a man who she wasn’t married to, but she was the first one Jesus chose to minister to in Sychar, Samaria.
It is only on the surface that the Samaritan Woman would be a strange person for Jesus to evangelize to this way. She was effectively chosen to usher fellow Samaritans to listen to Jesus, and many believed. What stood out about her was that she loved truth. She kept wanting Jesus to explain what he told her. When Jesus told her about her embarrassing life history, she took it in stride, decided that Jesus must have been a prophet, and sought out more wisdom from him.
What is most telling is that, when Jesus explained that it was time for people to worship God, not at any specific location, but in Spirit and truth, the Samaritan Woman immediately mentioned that the Messiah would reveal the truth. This would have been considered an extreme jump in logic in the respectable circles of the Jews. What Jesus explained, however, resonated with her anticipation of the Messiah and who he would be even if she did lack the full picture. She was truly ready to receive Jesus as Messiah and Lord because she was willing to worship God the way he wants to be worshiped. This is why Jesus chose to announce to her that he is the Messiah.