Sept 5 | Jesus's Uncomfortable Questions: Why Christ Asked Questions That Made Everyone Squirm
The Teacher Who Questioned Everything
When we picture Jesus teaching, we often imagine Him delivering sermons and sharing parables. But here's something remarkable: Jesus asked approximately 300 questions throughout the Gospels, while only directly answering about 8 questions posed to Him. This striking ratio reveals something profound about His teaching method - Jesus wasn't interested in giving easy answers. He was interested in transformation.
The uncomfortable questions Jesus asked weren't meant to shame or embarrass. They were surgical instruments, precisely designed to cut through religious pretense and touch the deepest parts of the human heart. These questions still echo through time, challenging us today just as powerfully as they challenged His original audience.
The Pool of Bethesda: When Healing Seems Cruel
"Do You Want to Get Well?" - The Question That Changes Everything
In John chapter 5, we encounter one of Jesus's most seemingly insensitive questions. At the Pool of Bethesda, surrounded by multitudes of sick and disabled people, Jesus approaches a man who had been paralyzed for 38 years. Instead of immediately healing him, Jesus asks, "Do you want to get well?"
At first glance, this question appears cruel. Why would Jesus ask someone who's been paralyzed for nearly four decades if they want to be healed? It's like asking someone dying of thirst if they'd like water. But Jesus saw something we often miss - sometimes we become so comfortable with our dysfunction that healing becomes scarier than staying broken.
The man's response is telling. He doesn't eagerly say "Yes!" Instead, he makes excuses: "I have no one to help me into the pool when the water is stirred. While I am trying to get in, someone else goes down ahead of me." After 38 years, this man's entire identity was built around being the victim at the pool. Everyone knew him as the paralyzed man. He had a spot, a routine, probably received charity from passersby.
Jesus's question wasn't about physical healing alone. He was asking: "Are you ready for your entire life to change? Because healing means no more excuses. No more pool. You'll need to work, take responsibility, and stop blaming others for your condition."
The Three Types of Uncomfortable Questions Jesus Asked
1. Questions That Expose Our True Motivations
Jesus had an uncanny ability to see through religious flattery and expose what people really wanted. When the rich young ruler ran up to Him (and Mark specifically notes he RAN - imagine this wealthy man hiking up his robes, sprinting to catch Jesus), he began with flattery: "Good teacher, what must I do to inherit eternal life?"
Jesus's response? "Why do you call me good? No one is good except God alone."
This wasn't Jesus fishing for compliments or having an identity crisis. He was asking: Are you just flattering me to get the answer you want? Or do you actually recognize who I am? The question forced the young man to examine his own heart. Was he approaching Jesus as just another rabbi with interesting teachings, or as the Son of God?
Similarly, when the Pharisees tried to trap Jesus with questions about taxes, marriage, or the Sabbath, He often responded with counter-questions that exposed their real agenda. "Whose image is on this coin?" wasn't really about currency - it was about revealing their hypocrisy in using Roman money while claiming to despise Roman rule.
2. Questions That Reveal Our Hiding Places
Throughout Scripture, we see a pattern: God asks questions not because He needs information, but because we need to acknowledge truth. The very first question in the Bible after the fall is God calling out to Adam and Eve: "Where are you?"
God knew exactly where they were. He wanted them to acknowledge they were hiding.
Jesus continues this divine tradition. After Peter's three denials, the resurrected Jesus finds Peter by another charcoal fire - the same type of fire Peter stood by when he denied knowing Jesus. Three times Jesus asks, "Simon, son of John, do you love me?"
Once for each denial. Not to shame Peter, but to heal him. Each question was an opportunity for Peter to affirm what he had previously denied. It was restoration through interrogation, healing through uncomfortable honesty.
When Jesus asks us "Why do you worry?" or "Where is your faith?" He's not seeking information. He's inviting us to examine our own hiding places - those areas where we claim to trust God but actually rely on our own understanding.
3. Questions That Address Root Issues Rather Than Symptoms
Perhaps the most profound aspect of Jesus's questions is how they bypass surface problems to address root issues. The paralyzed man thought his problem was mobility. The rich young ruler thought his problem was not knowing the right religious formula. The disciples in the storm thought their problem was the weather.
But Jesus's questions revealed deeper truths:
To the paralyzed man: Your real paralysis might be spiritual
To the rich ruler: Your wealth is your true god
To the disciples: Your faith hasn't moved from your head to your heart
In Luke 18, blind Bartimaeus screams from the roadside, "Son of David, have mercy on me!" Everyone tells him to be quiet, but Jesus stops and asks what seems like an obvious question: "What do you want me to do for you?"
Why ask a blind man what he wants? Because Jesus doesn't assume. He doesn't override human will. He requires us to articulate our deepest needs, to take ownership of our desire for transformation.
The Mathematical Precision of Christ's Questions
The 300-to-8 Ratio: A Teaching Strategy
The fact that Jesus asked roughly 300 questions while only directly answering 8 reveals a deliberate pedagogical strategy. Consider some of His most powerful questions:
"Who do you say I am?" - The question of identity
"What good is it if a man gains the whole world but loses his soul?" - The question of values
"Why do you call me 'Lord, Lord' and not do what I say?" - The question of authentic faith
"Do you believe I am able to do this?" - The question of trust
"What do you want?" - The question of desire
"Why are you thinking these things in your hearts?" - The question of hidden thoughts
"If I tell you the truth, why don't you believe me?" - The question of resistance
Each question serves multiple purposes: it engages the listener, requires self-examination, and often contains its own answer within the question itself.
The Storm and The Silence: Questions in Crisis
One of the most revealing episodes about Jesus's use of questions occurs during the storm on the Sea of Galilee. The disciples, several of whom were experienced fishermen, recognized this storm as life-threatening. Jesus was asleep on a cushion (Mark includes this detail, emphasizing how comfortable Jesus was while they panicked).
They wake Him with an accusation disguised as a question: "Teacher, don't you care if we drown?"
After calming the storm, Jesus asks two questions: "Why are you so afraid? Do you still have no faith?"
Notice the present tense. Not "Why WERE you afraid?" but "Why ARE you afraid?" Even after witnessing the miracle, even after seeing His power over nature, Jesus recognizes their fear persists. Sometimes we're more comfortable with our storms than with the calm that comes after Jesus speaks.
Modern Applications: When Jesus's Questions Meet Our Lives
The Workplace Question: "What Do You Want Me to Do for You?"
In our professional lives, we often approach God like the blind man - we shout general prayers for "blessing" or "success" without articulating specific needs. Jesus's question forces us to be precise. Do we want a promotion? Better relationships with colleagues? The courage to change careers? Until we can articulate it, we might not really know what we're asking for.
The Relationship Question: "Do You Love Me?"
This isn't just about our relationship with Christ. It's about all our relationships. Jesus's question to Peter reminds us that love isn't just a feeling or a belief - it's demonstrable through action. "Feed my sheep," Jesus tells Peter. Love requires service, sacrifice, and commitment.
The Identity Question: "Who Do You Say I Am?"
In an age of social media personas and carefully curated online identities, Jesus's question about His identity forces us to examine our own. If Jesus is Lord, what does that make us? If He is teacher, are we students? If He is Savior, do we acknowledge our need for saving?
The Uncomfortable Grace: When Questions Become Gifts
The paralyzed man never actually answered Jesus's question about wanting to be well. He deflected with excuses. Yet Jesus healed him anyway. This reveals perhaps the most beautiful truth about Christ's uncomfortable questions - they're not tests we must pass to earn His favor. They're gifts that lead to transformation, whether we're ready or not.
Sometimes grace shows up even when we can't articulate what we need. But the questions still hang in the air, patient and persistent, waiting for us to engage with the deepest truths about ourselves and our God.
Living in the Questions
Jesus's uncomfortable questions aren't relics of ancient religious dialogue. They're living, active, and sharp as any two-edged sword. They pierce through our modern pretenses just as effectively as they challenged ancient prejudices.
The next time you read the Gospels, pay attention to Jesus's questions. Let them make you uncomfortable. Let them expose your hiding places, reveal your true motivations, and address your root issues. Because sometimes, the question you're avoiding is exactly the one that will set you free.
Remember: Jesus isn't interested in our religious performance or correct answers. He's interested in transformation. And transformation often begins with an uncomfortable question that we'd rather not answer - but must, if we want to experience the fullness of life He offers.
An Invitation to go Deeper….
If today’s message spoke to you, join the FaithLabz 30-Day Prayer Challenge and strengthen your connection with God’s unshakable love. You are never alone—let’s grow together!
