When Jesus Doesn’t Meet Our Expectations

When Jesus Doesn’t Meet Our Expectations
A Pastoral Reflection on Matthew 11:2–11

There was a season in my life when Mountain Dew was basically my morning coffee. By the time soda was fading out of my routine, I’d still treat myself on Friday mornings before heading to work at the prison. I’d swing by the vending machines outside Walmart, drop in my 35 cents, and walk into the facility with that cold can ready to start the day.
One particular Friday, right as I cracked open that can at my desk, the emergency call came over the radio. Hours later, after helping stop a suicide attempt, after the blood, the punches, the hospital, the shower, and the change of clothes—I returned to that can. No longer cold. No longer refreshing. Just… flat. The day had not met my expectations.
And isn’t that how life goes? Expectations can be a gift, but they can also set us up for deep disappointment.
It turns out a section of Matthew 11 is all about what happens when expectations collide with reality.

When Even the Strongest Believers Ask Hard Questions

Matthew tells us:
“Now when John heard in prison about the deeds of the Christ, he sent word by his disciples and said to him, ‘Are you the one who is to come, or shall we look for another?’”
— Matthew 11:2–3 (ESV)
John the Baptist—this bold, fiery preacher—now sits in the dungeon of Machaerus. Cold. Dark. Hopeless. And honestly? Doubt grows best in the dark.
John had expected a Messiah who would swing an axe at the root of injustice (cf. Matthew 3:10). A Messiah who looked more like King David with a sword than a rabbi healing the sick and preaching good news to the poor. John wasn’t wrong about judgment—he just didn’t yet see the timing of God’s kingdom.
So he asks, “Jesus… are You really the One?”
And, that question is not unbelief. That’s a believer wrestling honestly with pain.
If we’re honest, we’ve all been there too.
You prayed for healing that didn’t come.
You trusted God and still faced loss.
You lived faithfully but still encountered heartbreak.
And suddenly the question slips out:
“Lord… is this how it’s supposed to go?”

Jesus Answers Doubt with Scripture, Not Shame

Jesus responds with a gentle, Scripture-soaked assurance:
“Go and tell John what you hear and see: the blind receive their sight... the poor have good news preached to them.”
— Matthew 11:4–5 (ESV)
Jesus isn’t defensive. He isn’t irritated. He simply points John back to Isaiah:

• “Then the eyes of the blind shall be opened…” — Isaiah 35:5–6
• “The LORD has anointed me to bring good news to the poor…” — Isaiah 61:1

John would have recognized these immediately. Jesus is saying:
“John, the kingdom is unfolding exactly the way Scripture promised—just not the way you pictured it.”
And then Jesus adds:
“Blessed is the one who is not offended by me.”
— Matthew 11:6 (ESV)
In other words:
“Don’t trip over the ways I work that don’t match your expectations.”
Faith isn’t pretending life is easy.
Faith is refusing to walk away when God’s ways differ from ours.

Jesus Defends the Doubter

As John’s disciples leave, Jesus turns to the crowd—not to criticize John, but to honor him:
“What did you go out into the wilderness to see? … A prophet? Yes, I tell you, and more than a prophet.”
— Matthew 11:7–9 (ESV)
Jesus affirms John:

• He wasn’t weak.
• He wasn’t fickle.
• He wasn’t a man of luxury or political gamesmanship.

John’s doubts didn’t erase his calling.
And your doubts don’t erase yours either.
Then Jesus quotes Malachi 3:1:
“Behold, I send my messenger before your face…”
— Matthew 11:10 (ESV)
John was the hinge between the old covenant and the new—the final prophet preparing the way for the Messiah Himself.
And yet Jesus ends with this surprising statement:
“Among those born of women there has arisen no one greater than John the Baptist. Yet the one who is least in the kingdom of heaven is greater than he.”
— Matthew 11:11 (ESV)
Why are even the “least” in the kingdom greater?
Because John saw the Messiah coming—
but we see the Messiah crucified, risen, and reigning.
We live in the era John longed for.
We have the cross.
We have the resurrection.
We have the Holy Spirit.

What This Means For Us

John doubted in the dark.
We do too.
And Jesus meets us the same way He met John—in Scripture, in truth, in compassion.
When expectations crumble, go back to the Word.
Let Jesus remind you who He is, not who you assumed He would be.
I remember wrestling with doubt when I considered leaving a stable 20-year career to follow God’s call into ministry. Everything in me wanted certainty. But God was inviting me into trust.
Doubt is not failure.
Doubt is often the doorway to deeper faith.
And through every doubt, Jesus speaks:
“Look again. I am at work, even here.”

The Good News for Doubting Hearts

John prepared the way for Jesus.
But now—the Spirit of Jesus prepares the way in you.
Even in uncertainty.
Even in unanswered prayers.
Even when God doesn’t meet your expectations…
He is still faithful.
Thank God Jesus doesn’t crush doubting saints—
He lifts them.
And He’ll lift you too.
Grace and peace, friends. Let’s walk this journey with honest hearts and open Bibles—trusting the One who never abandons us in the dark.
Amen.