Turning to God with our Disappointments

Advent is often described as a season of waiting, but waiting is rarely easy. We wait for healing, for justice, for clarity, for prayers to be answered. Over time, waiting can become exhausting—sometimes even disappointing. What do we do when our readiness for God quietly turns into disappointment with God?

Matthew 11:1–11 invites us into that very tension through the surprising experience of John the Baptist. Earlier in the Gospel, John appears bold, fiery, and unshakably confident. He is the forerunner, the one crying out in the wilderness, preparing the way for the Lord. He knows who Jesus is. He baptized Him. He heard the voice from heaven saying, “This is my beloved son with whom I am well-pleased (Matthew3:17). John was ready.

But in this passage, we encounter a different John. He is in prison for calling out the corruption of Herod Antipas. Days stretch into weeks, weeks into months. Jesus is active—preaching, healing, teaching—but not in the way John expected. The axe John proclaimed does not seem to be falling (Matthew 3:10). And so, from a prison cell, John sends messengers to Jesus with a startling question: “Are you the one who is to come, or should we look for another?”

It is a vulnerable question, and maybe an awkward one. It is asked publicly, in front of crowds. Yet it is also deeply human. John’s expectations no longer align with his experience. The gap between what he expected and what he is experiencing feels wide. And in that gap, doubt grows.

Many of us know that gap well. Disappointment is often born there. I often describe disappointment as the gap between our expectations and our experience. The bigger the gap, bigger the disappointment. We expected the job opportunity, but we experience a layoff. We expected healing, but we receive a diagnosis. We expected justice, but we see corruption persist. Advent meets us in that space honestly. A weary world waits and sometimes wonders if it should look elsewhere.

What is striking in this passage is not that John doubts, but what he does with his doubt. He does not turn away from Jesus; he turns toward Him. He brings his question directly to the Lord.

Jesus’ response is tender and steady. He does not rebuke John for asking. Instead, He points to what is happening: the blind see, the lame walk, the poor hear good news. Jesus is fulfilling the promises of Isaiah—but not on John’s timetable. The implication is gentle but clear: I am who I say I am, even if I do not work the way you expected.

There is a warning here for us. In seasons of disappointment, we are often tempted to focus only on what God is not doing. Over time, that focus can distort who we believe God to be. C.S. Lewis reflected on this in his book A Grief Observed after he lost his wife to cancer. He writes,

Not that I am (I think) in much danger of ceasing to believe in God. The real danger is of coming to believe such dreadful things about Him. The conclusion I dread is not ‘So there’s no God after all,’ but rather ‘So this is what God’s really like. Deceive yourself no longer.

Lewis is telling us that the danger of suffering is not losing belief in God, but coming to believe dreadful things about Him. Disappointment can quietly reshape our theology if we let it.

Jesus then offers a blessing: “Blessed is the one who is not offended by me.” He is not saying blessed are those who never doubt. If that were the case, none of us would qualify. He is saying blessed are those who doubt without falling away—those who refuse to let disappointment become the final word.

After John’s messengers leave, Jesus turns to the crowd and does something remarkable: He publicly honors John. He does not minimize his faith because of his doubt. He celebrates his faithfulness and calls him great. John’s questions do not disqualify him from love, honor, or belonging.

Yet Jesus also points beyond John to something even greater—the kingdom of heaven. Entry into this kingdom does not depend on certainty or performance. It depends on trust in Christ. Even the least in this kingdom stands secure, not because of what they have done, but because of what Jesus is doing.

That is good news for weary people. Advent does not promise quick answers or immediate resolution. John remains in prison. His circumstances do not change. The change that happens is where his doubt is carried.

So where does this leave us? Not with every question resolved, but with a Person who welcomes our questions. Advent invites us to bring our disappointment to Jesus rather than letting it drive us from Him. It reminds us that God may not move on our timeline, but He has come near.

For those who are tired of waiting, who feel the gap between expectation and experience widening, the invitation still stands: turn toward Jesus. Blessed are those who wait without walking away. And for grace such as that, we pray—even now—to trust Him more.