Keep Awake

Preaching Notes

Focus Text: Matthew 25:1-13 

When did “woke” become such an offensive word in our polarized society? Perhaps the better question is, how? How did such an innocuous word become the ultimate put-down, the prime dismissal of whole groups of people and ways of thinking? Being awake, keeping awake, is a recurring theme for Jesus. This whole series of stories, of which there are four, we must note, begins with the call to keep awake. We have to grasp this invitation; we have to live into the possibility that being awake – being woke – is not only possible, but necessary for the follower of Christ.

Before we unpack the text, we need to face realities. Preacher, you aren’t going to redeem the word “woke” in this sermon, even if you wanted to (and you may not). As “woke” has come to be defined in our political rhetoric – or misrepresented, if you will – it might not be worth the effort. Yet, using the title we gave this week’s theme might cause discomfort among some in your pews. It might cause echoes, unwanted echoes in the minds and hearts of the hearers. It might raise defenses. So, tread carefully.

Four stories? Chapter 25 of Matthew’s Gospel only has three. True, but back up. This thread begins in chapter 24. It begins with a discourse on what really matters, occasioned by the disciples’ fascination with the Temple. The long discourse that follows has been presented as instructions for going to heaven or entering the kingdom of God. Indeed, there does seem to be an emphasis on eternity. Yet for Jesus, entry into eternity results from living with eternal, or kingdom, values today. In essence, this is about how to live today. The parables that follow the discourse are not simply about the next world, but about living in this one.  

That isn’t our text for this week, true. But it is the foundation of all of chapter 25 in Matthew. We skip over the first of the four parables: the wise and wicked slaves given charge over the master’s house. But all four parables are launched with the command to keep awake.  

At last, we get to this week's text! Our parable begins with “the kingdom of heaven will be like this.” This is one of those parables we would prefer to skip. It feels wrong to us. It seems to go against the faith we have learned from Jesus. Sharing seems fundamental to who we are called to be as followers of Christ, so saying there isn’t enough for you and for us seems selfish. So, how do we unpack this story in a helpful way? Preachers have wrestled with this passage for as long as we have attempted to preach it.

Does it help to dive into the story's historical context and explain the wedding customs of the time? Maybe. It could allow the hearers to sit a little more comfortably with a complicated tale. It might, however, give people an out because their practice differs from ours, so we cannot relate. This is what “othering” means. It gives permission to set it aside as a quirky cultural event that we can’t duplicate. That isn’t the purpose of the sermon that delves into the history; we understand that. It is, on occasion, an unfortunate result. And this parable isn’t really about wedding behavior anyway.

So, what is it about? Jesus tells us it is about being ready. When I was a kid, my mom would make sure I was ready for church. She would inspect the state of my clothes and the cleanliness of my hands and face, and then she would say, “Sit there and don’t do anything until it is time to go to church.” I was ready. And I had to be sure not to do anything to get myself unready, no risk taking, no adventures. Just sit there quietly, being ready. My mom knew me. But I don’t think she was giving me a parable about being ready.  

Jesus doesn’t say, "Sit still and don’t get messy.” He says to keep awake. “For you know neither the day nor the hour.” But what does that mean? Does our ignorance hinder our living? Does the lack of knowledge of the movement of the returning Messiah cripple our efforts, our ministry, our lives? Or does not knowing free us to live fully every day?  

Keeping awake is an invitation to engage in the joy of living. It is to embrace the presence of the kingdom. It is to recognize the kin-dom in the fellowship of the community around us. Keeping awake is an invitation to live the abundant life Jesus speaks of in John 10:10 (NRSV): "I came that they may have life, and have it abundantly."  

One curious observation is that both the wise and the foolish bridesmaids (or virgins – which might be another curious diversion. Is the reference about marital status or naivety?) behave in the exact same way—except for one difference, extra oil. So, what does the oil represent? That’s the question that captures everyone’s attention. Many have argued that the oil represents the good works that the one awaiting the Messiah's return performs in the meantime. That makes sense. That is why the wise ones are unwilling to share, because they can’t. But others point out that this hints at a works-righteousness theology that says that unless you do these things, you will be excluded from the wedding celebration.  

So what are we left with? It isn’t clear, to be honest. But what if the story is about presence? Waiting for a presence, to be sure, but also being present in the life of waiting. Keep awake, Jesus says, stay present. Pay attention to what is happening around you, in you, and to you. Listen to those who want to tell you their stories and hear the echoes of the story of the one who comes. Weep with those who weep and rejoice with those who rejoice: that’s the oil that brings light into a world too accustomed to darkness. “Keep awake” is a call to presence, to embodiment, to mindfulness. It’s not a selfish presence, however. It’s a presence awake to those around us. Bonhoeffer was speaking of this presence when he wrote, “We must be ready to allow ourselves to be interrupted by God. God will be constantly crossing our paths and canceling our plans by sending us people with claims and petitions” (Dietrich Bonhoeffer, Life Together: The Classic Exploration of Christian Community, cited in The Caring Congregation’s  Weekly Care Note email on April 28, 2026). We don’t know what day Christ will return. We don’t know what day we will catch a glimpse of him in the people and the needs around us. We don’t know that it just might be this day. So, keep awake.

Rev. Dr. Derek Weber, Director of Preaching Ministries, served churches in Indiana, Arkansas, and the British Methodist Church. His PhD in preaching and media is from the University of Edinburgh. He has taught preaching in seminary and conference settings for more than twenty years.