When Faith Has Questions

Matthew 11 moves from Jesus sending his disciples out like lights in the darkness into a moment where one of Jesus’ strongest witnesses is sitting in a dark place of his own. Jesus had already set the expectation that the kingdom would be seen through healing, deliverance, salvation, and transformed lives, but also through rejection, persecution, and pain. The question rises when life does not match the picture, when the thing ordered does not arrive in the right size, shape, or condition.

Lamentations, Proverbs, Ecclesiastes, and Job all press the same truth into the room: suffering comes to all, and hard times come even to good people. Job stands as the clearest witness, because God himself called him blameless, and yet loss, grief, sickness, and confusion still came to his house. Job’s cry, “I know that my redeemer lives,” becomes the anchor for trusting God’s character when God’s plan cannot be traced.

John the Baptist makes Matthew 11 feel almost unbelievable. John was not just some guy. His birth was announced by an angel, he baptized Jesus, he saw the Spirit come down, he pointed to Jesus as the Lamb of God, and he prepared the way for the kingdom. Yet John ends up in prison because he confronted Herod with the word of God. His question to Jesus, “Are you the one who is to come, or should we expect somebody else?” is really the cry underneath so many cries: if Jesus is really the Messiah, then why is this still happening?

Jesus does not shame John for asking. Jesus points him back to the evidence of the kingdom: the blind see, the lame walk, lepers are cleansed, the deaf hear, the dead are raised, and good news is preached to the poor. Jesus recenters John, not by pretending the prison is not real, but by showing that the kingdom of God is still on the move.

Jesus then speaks about John with honor. John’s lowest moment does not become his definition. One season of doubt does not erase a lifetime of faithfulness. Satan lies and says questions mean failure, but God is big enough for honest questions. Faith is not the absence of questions. Faith chooses where to trust while waiting for the answer.

The body of Christ becomes the place where hurting people find hope by bringing questions to Jesus and by telling the stories of God’s faithfulness. Testimony beats back the enemy because every honest story says, even in pain, “God has been faithful.”

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Key Takeaways

• 1. Hard times hit faithful people [01:06:15] John loved God, served God, and sacrificed comfort, reputation, and safety, yet John still ended up in prison. Faithfulness does not create a force field around pain. The Bible refuses the easy math that obedience always produces immediate comfort. A believer’s suffering may be unfair, but unfair suffering is not proof that God has walked away. [66:15]
• 2. Jesus receives honest questions [01:09:36] John’s question came from a prison cell, not from a casual debate. Jesus did not crush him for asking, and Jesus did not treat his confusion as rebellion. Honest pain can still be an act of faith when it is carried toward Christ instead of away from him. God is big enough to carry the question that feels too heavy to say out loud. [69:36]
• 3. Unanswered prayers need wider sight [01:10:49] Jesus answered John by pointing to the blind seeing, the lame walking, the dead being raised, and the poor hearing good news. One unanswered prayer can become so loud that it drowns out every other sign of God at work. Jesus does not deny the prison, but he does widen the view. The kingdom can be moving even while one painful door remains locked. [70:49]
• 4. Doubt does not erase faithfulness [01:15:28] Jesus did not define John by his weakest moment. Jesus called him more than a prophet while John was still wrestling with confusion. A season of doubt may reveal pain, exhaustion, or disappointment, but it does not rewrite a life of obedience. Christ sees more than the moment that feels most embarrassing. [75:28]
• 5. Testimony beats back the enemy [01:23:45] The enemy wants isolation, silence, and the lie that nobody else is struggling. Testimony opens a window and lets another believer see that God has been faithful in real lives, not just in theory. A shared story can become strength for someone still in the middle of the fight. The blood of the Lamb and the word of testimony push back darkness together.
  
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Youtube Chapters

• [00:00] - Welcome
• [50:02] - When Life Does Not Match Expectations
• [55:56] - Jesus Sends Lights Into Darkness
• [58:14] - The Unspoken Deal With God
• [60:00] - Job Trusts His Living Redeemer
• [61:41] - Can Jesus Be Trusted In Pain?
• [64:50] - John’s Prison Question
• [70:00] - Jesus Points To Kingdom Evidence
• [74:35] - Jesus Honors John’s Faithfulness
• [77:42] - God Is Big Enough For Questions
• [81:14] - Bring The Questions To Jesus
• [83:14] - Remember God’s Faithfulness
• [85:39] - A Time To Pray And Respond

Bible Reading

Matthew 11:2-6
“When John, who was in prison, heard about the deeds of the Messiah, he sent his disciples to ask him, ‘Are you the one who is to come, or should we expect someone else?’ Jesus replied, ‘Go back and report to John what you hear and see: The blind receive sight, the lame walk, those who have leprosy are cleansed, the deaf hear, the dead are raised, and the good news is proclaimed to the poor. Blessed is anyone who does not stumble on account of me.’” [01:04:50]

Job 19:25
“For I know that my redeemer lives, and at the last he will stand upon the earth.”

Isaiah 35:5-6
“Then will the eyes of the blind be opened and the ears of the deaf unstopped. Then will the lame leap like a deer, and the mute tongue shout for joy.”

Revelation 12:11
“They triumphed over him by the blood of the Lamb and by the word of their testimony; they did not love their lives so much as to shrink from death.”

Observation questions

1. In Matthew 11:2-6, what specific question did John send to Jesus from prison, and what specific signs did Jesus point to in his reply? [01:10:00]
2. What details make John the Baptist’s question feel so surprising, given who he was and what he had already seen of Jesus? [01:03:28]
3. What are some of the examples Scripture gives that suffering can come even to people who are trying to live faithfully before God? [01:00:00]
4. After John’s disciples left, how did Jesus speak about John to the crowd, and what did that show about how Jesus viewed him in that moment? [01:14:35]

Interpretation questions

1. John’s question was basically, “If Jesus really is the Messiah, why am I still in prison?” What does that reveal about how pain and disappointment can shake a person’s expectations of God, even when that person has walked closely with him? [01:09:36]
2. Jesus did not remove the prison first; he pointed John to the evidence that the kingdom was still moving. Why might that kind of answer be important for someone whose own prayer is still unanswered? [01:10:49]
3. Job said, “I know that my redeemer lives,” even before his situation was resolved. What does that kind of statement mean in real life when someone cannot trace God’s plan but still wants to trust God’s character? [01:21:14]
4. Jesus honored John publicly instead of defining him by his weakest moment. How should that shape the way believers think about seasons of doubt, confusion, or emotional exhaustion in their own lives and in the lives of others? [01:15:28]

Application questions

1. Where does life feel most different from what was hoped for or expected right now? What question keeps rising in that place, and what would it look like to bring that question honestly to Jesus instead of hiding it? [01:22:32]
2. Is there one unanswered prayer that has become so loud that it is hard to notice any other signs of God’s work? What might help widen the view again and remember that the kingdom can still be moving even while one door stays closed? [01:11:29]
3. When hard times come, is there a tendency to assume God is disappointed or far away? What would change this week if Jesus’ words about John were taken seriously—that one painful season does not erase a life of faithfulness? [01:15:46]
4. What has helped in past seasons to keep trusting God’s character when his plan made no sense? Are there Psalms, habits, prayers, or conversations that have become lifelines and may need to be picked up again? [01:20:14]
5. What is one honest question that would be asked of God today if there were no fear of being judged for it? What makes that question hard to say out loud? [01:23:14]
6. Where has God’s faithfulness been seen recently, even if only in a small way? How might sharing that story strengthen someone else who is still in a prison-like season? [01:23:45]
7. Testimony helps beat back the enemy’s lies. What story of God’s faithfulness—from this week or from years ago—needs to be spoken more openly so that silence and isolation do not win? [01:25:21]