These two encounters seem to be linked to one and other intentionally. They tell us much on their own, but possibly even more when we compare them to each other.
In both encounters we have characters who Jesus reveals to that he is the fulfillment of Old Testament promises. In both encounters Jesus ends up in theological conversations, one about baptism (Nicodemus) and place of worship (Samaritan woman). Both also seem intrigued by Jesus and are puzzled by many of the things that he says.
The contrasts are also many. Nicodemus meets with Jesus in the secrecy of night. This is because he has much at stake. He is an established religious figure in the community, and could lose much of his status by being associated with person such as Jesus. It is better for Nicodemus to visit with Jesus in the night, so he can explore and hear his ideas without facing judgment by his peers. The Samaritan woman also meets Jesus in isolation but it is during the day. She has nothing to lose because she has already lost it all. We come to discover that she has had multiple husbands and is probably at the well at this most inconvenient time because she has been shunned by the other women of the town. She has no religious status and even by the Samaritan belief system God would surely not be pleased with her or have room for her in the community. One must meet in secrecy the other as an outcast.
What is also interesting about the Samaritan woman encounter is that many social boundaries are crossed in this engagement. She is a woman, a Samaritan and sexually immoral three major strikes for why Jesus should not give her the time of day. Yet we also see that she is a learner. As Jesus gives her more and more information she acts on it. She is a great example of a disciple because as she moves from ignorance to knowledge she begins to act upon it. Even going into her town and telling all to come and meet Jesus. Some think that she is trying to divert Jesus after he confronts her sexual impurity by asking where to worship, but I think there is more there. In reality for a Samaritan or Jew the natural response one would have been to go to the temple to atone for sins. It could be that as she was confronted with her sins by Jesus she wanted to act and do what she believed one is supposed to do for repentance; go to temple.
By putting these two stories together we get a glimpse of Jesus’ forthcoming missional movement. As he will command his followers to go to Judea, Samaria and the ends of the earth. It is like a sneak preview of the mission that is to come. It will know no bounds and be for everyone. For the ultra religious and for the outcasts, they all need to be told of the “living water” that Jesus offers.