Jesus is heading to Galilee, but in the middle of the route, there is Samaria. Not only did Jesus go through Samaria, but he "had to go" through the area (4:4). In the ancient world (from 4:9), Jews and Samaritans do not even get along together. The lack of connection may be why Jesus intended to go through Samaria; he wanted to end the streak of Jew-Samaritan hostility.
Eventually, Jesus wanted to take a break from travelling by resting near Jacob's well. While the disciples were out getting food, a Samaritan woman approached a well. Upon seeing the woman, Jesus asked for a favor -- to offer him a drink (4:7).
So why would Jesus even ask a Samaritan woman to get water? Jesus saw dignity and value in her job, and Kenneth Bailey and DT Niles commented on how Jesus gave the woman an opportunity to serve rather than "serv[ing] from a position in power" (Christianity Today). It's possible that Jesus asks permission to access the water that the Samaritans have (to introduce the idea that Samaritans can work with Jews without being unclean). But more importantly, it's God's intent for Jesus to counter cultural and historical norms on Jew-Samaritan hostility.
From 4:9, not only did Jews not get along with Samaritans (and vice versa), but they do not even "associate" together! In fact, the Samaritan woman herself was pretty surprised on the type of interaction. She did not expect a Jew to ask a Samaritan woman (of all people) regarding drinks (note that it's atypical for a Jew to talk to another woman). However, the break in cultural expectations lead to an impactful conversation for the woman -- and the Samaritan community.
Jesus broke the convention by loving and reaching out to people completely different from herself. The Samaritan woman had different gender, people group, and even religious beliefs (as we'll see later). So today, for those who walk with Jesus, it's important to show compassion to people of different gender (this includes people of the LGBTQ+ community, even though we may not agree with them on everything), different skin color, and even different religious beliefs (even though we may not agree with them on everything). We don't have to necessarily agree with them on every decision they make or think that their choices are a good idea, but it's important for them to see Jesus's compassion breaking through cultural expectations.
And it's more important for us to see Jesus breaking through cultural expectations for our behalf. We may be treated as societal outcasts and even did some bad screw-ups, but that did not stop Jesus from loving us.