Grace in the Questions
Study Guide Week Ten
Can You Drink the Cup?
Matthew 20:20–23
Enter the Scene
The request comes with confidence.
They have been walking with Jesus. They have seen enough to believe that something is unfolding
—something significant, something that will lead somewhere. The language of kingdom has taken
hold of their imagination, even if they do not yet understand its shape.
So they come forward with a question of their own.
“Grant that one of these two sons of mine may sit at your right hand and the other at your left, in your kingdom.”
It is not a careless request. It is thoughtful, intentional, even faithful in its own way. They believe Jesus
is going somewhere, and they want to be near him when he arrives. They are not asking to leave him.
They are asking to be close to him. But they are imagining the destination without understanding the path.
And Jesus does not answer their request directly.
He asks a question instead.
The Question
“Are you able to drink the cup that I am about to drink?” (Matthew 20:22)
The question interrupts their expectation.
Jesus does not speak about position.
He speaks about participation.
Not where they will sit,
but what they will share.
What This Reveals
We often desire the life of Jesus without understanding the cost of following him.
The disciples are not wrong to want closeness. They are not wrong to desire to be with Jesus
where he is going. But their vision is shaped by what they can see—honor, nearness, significance.
Jesus names what they cannot yet see.
The “cup” in Scripture carries weight. It is not simply an experience. It is something received,
something entered into fully—often marked by suffering, surrender, and trust in the midst of
what cannot be controlled.
To drink the cup is to share in the life of Jesus as it actually unfolds—not as it is imagined.
And this is where the question presses.
Are you able?
Not in strength.
Not in certainty.
But in willingness.
The disciples answer quickly. “We are able.”
Their response is sincere. But it is not yet formed by understanding. They cannot yet see where
the path will lead, what it will require, or how deeply it will reshape them.
And Jesus does not dismiss them.
He does not correct them sharply or withdraw the invitation. He allows their answer to stand,
even as its meaning will unfold slowly over time.
This is what the question reveals: following Jesus is not only about where we hope to arrive.
It is about what we are willing to enter along the way.
Closeness to Jesus is not defined by position, but by participation.
Reflection
Take your time here. Let the question come close.
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What kind of life are you expecting from following Jesus?
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Where do your expectations feel shaped by comfort, success, or recognition?
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What parts of following Jesus feel unclear or costly right now?
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Where do you sense resistance—not to belief, but to what obedience might require?
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What would it mean to follow Jesus even if the path looks different than you imagined?
Let your answers be honest. Do not rush to resolve them.
Stay With It
Do not move too quickly to say yes.
There is a natural impulse to respond as the disciples did—to affirm willingness before
fully understanding what is being asked. But Jesus does not rush the moment. He allows
the question to remain, creating space for reflection before response.
Stay with what is being uncovered.
Notice where you feel open, and where you feel hesitant. Notice what you are willing to carry, and
what you would rather avoid. These are not failures. They are places where formation is already beginning.
You are not being asked to prove your readiness.
You are being invited to recognize your willingness.
Practice
Sit quietly with the question:
Am I willing to follow where this leads?
Do not answer quickly. Let the question rest with you.
Notice what rises—desire, hesitation, uncertainty.
If a next step becomes clear, hold it gently.
Do not rush it. Let willingness take shape slowly.
Optional Journaling (Deeper Practice)
Write without editing:
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“What I hope following Jesus will look like is…”
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“What I am hesitant to face is…”
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“If I am honest, I am not sure I am ready for…”
Let the words come without correction.
Scripture Connection
“Whoever does not carry the cross and follow me cannot be my disciple.” (Luke 14:27)
Following is not only movement.
It is participation in a way of life.
Breath Prayer
Inhale: Jesus, I am willing
Exhale: Lead me where you go
Repeat slowly, allowing the words to remain open if they need to.
Closing Thought
The disciples wanted to be near Jesus in his kingdom.
They did not yet understand what that nearness would require.
“Can you drink the cup?”
The question remains—not to discourage you, but to deepen your
understanding of what it means to follow.
Stay with it long enough, and you may begin to discover that the way
of Jesus is not something we admire from a distance,
but something we are invited to share—
step by step,
with him.