Advent Waiting: Trusting God's Unexpected Ways

In Advent we learn to wait. I told a simple story about Ralphie from A Christmas Story and the ache of wanting one gift, only to open a box and find something else. That ache is not just about Christmas; it’s the ache of life and prayer when our hopes don’t show up on our timetable or in the shape we imagined. John the Baptist knew that ache too. From Herod’s dungeon he sent messengers to Jesus, asking, “Are you the One?” He had proclaimed Jesus boldly, but in a dark and lonely season he faced his own questions about God’s timing and methods.

Jesus didn’t scold him. He sent John back to Scripture: the blind see, the lame walk, lepers are cleansed, the deaf hear, the dead are raised, and the poor hear good news (Isaiah 35). In other words, God was doing exactly what He promised—just not in the way people expected. That’s why Jesus says, “Blessed is the one who is not offended by me.” Disappointment can turn into a stumbling block when our unspoken expectations harden into demands. Advent invites us to check our expectations against God’s Word and God’s character.

James 5 calls us to patient endurance like a farmer who waits for early and late rains. Waiting isn’t idleness; it’s training. Establish your heart, James says, and practice the habits of a waiting people: forbearance instead of grumbling, simple truthfulness, prayer over hurts, songs over joys, confession and mutual intercession, seeking the wandering, all rooted in the mercy of God. These practices don’t shorten the road; they make us strong enough to walk it well.

I said it’s good for kids to get bored on long road trips because it builds capacity. The same with us: as we wait with prayer, confession, forgiveness, fasting, and song, we actually grow more able to wait. We glimpse God’s goodness in small ways and our hearts steady. Advent’s music gives us a voice for this: “O come, O come,” and the psalmist’s “How long, O Lord?” Honest songs train hopeful hearts. And like the father in the film who had “one more gift,” our Father’s heart, revealed in Jesus and confirmed in the resurrection, assures us there is more to come. We can wait a little longer—because we are waiting with Him.

Key Takeaways

• 1. Don’t stumble over unmet expectations Our disappointments often come from assuming God must act on our timeline and in our preferred way. Jesus warns that offense at His ways can trip us up more than the adversity itself. Bringing our assumptions into the light of His words protects our trust from the quiet erosion of entitlement. Faith matures when we learn to receive the real Jesus, not the one we scripted. [33:01]
• 2. Let Scripture reset your hopes When John doubted, Jesus pointed to Isaiah’s promises fulfilled in real time: sight, cleansing, resurrection, and good news to the poor. Scripture trains our imaginations so we can recognize God’s work when it arrives in unfamiliar clothing. Hopes rooted in the text can flex yet endure, because they lean on what God has actually pledged. [36:02]
• 3. Waiting forms us into readiness James pictures a farmer who works while he waits—preparing for fruit he cannot manufacture. Spiritual waiting is not passivity; it is disciplined attentiveness that makes us capable of receiving what God gives. We become people who can carry blessing without breaking, because patience has strengthened the frame of our souls. [38:28]
• 4. Build capacity for steadfast patience Capacity grows by practice. Like children learning long roads without constant entertainment, we learn longer obedience through repeated, ordinary faithfulness. As we pray, confess, forgive, and sing in the in‑between, God enlarges our hearts to hold both longing and joy at once. Over time we discover we’re less frantic, more steady, and more free. [43:27]
• 5. Pray your delay with honest songs Advent’s “O come” and the psalmist’s “How long?” are not complaints but covenants of trust voiced aloud. Honest prayer names reality without surrendering hope, and in doing so keeps cynicism from hardening our hearts. These songs don’t just express waiting; they shape it into worship. [46:02]

Youtube Chapters

• [00:00] - Welcome
• [09:49] - Advent joy; Collect and intercession
• [14:38] - Blessing the children
• [26:28] - A Christmas Story and longing
• [28:54] - When prayer meets disappointment
• [30:07] - John the Baptist’s question to Jesus
• [33:01] - Expectations and the unoffended heart
• [35:19] - Isaiah’s signs of the Kingdom
• [36:40] - James 5: learning to wait
• [39:56] - Practices for a waiting people
• [42:22] - Learning patience on the road
• [46:30] - Advent songs and the Father’s heart
• [55:39] - Communion: Invitation and Prayer
• [1:17:05] - Benediction and sending

1. In Matthew 11:2–6, John’s disciples go to Jesus with a direct question about whether he is the Messiah. What differences do you notice between John’s earlier public witness (e.g., “Behold the Lamb of God”) and his question now in prison? [30:07]
2. Jesus answers by pointing to signs from Isaiah (the blind see, the lame walk, lepers cleansed, the deaf hear, the dead raised, the poor hear good news). Which of those concrete signs stands out most to you when you hear Jesus describe his work? Why? [35:19]
3. Jesus says, “Blessed is the one who is not offended by me.” In the passage and the sermon illustrations, how is offense connected to unmet expectations? What exactly does Jesus warn against here? [33:01]
4. James uses the farmer waiting for early and late rains as an image of patient endurance. What actions or images in that section show waiting as active work rather than passive idleness? [38:28]

1. How does Jesus’ appeal to Isaiah’s promises (sight for the blind, liberty for the oppressed, good news to the poor) reframe the disciples’ and John’s expectations about what the Messiah would do? [35:19]
2. What does the statement “Blessed is the one who is not offended by me” imply about the relationship between expectation and faithfulness? How might hardened expectations become a spiritual stumbling block? [33:01]
3. In what ways does James’ farmer image change the group’s understanding of what “waiting for the Lord” looks like in ordinary life? What kinds of preparation or cultivation does waiting require? [38:28]
4. What role do community practices named in James (confession, mutual prayer, anointing and singing) play in sustaining steadfastness during long seasons of waiting? [39:56]

1. Unmet expectations can harden into demands that cause offense at God. Which particular expectation in your life feels most like a demand right now (a healing, a relationship, a job, a timing)? What would it look like this week to bring that expectation before Scripture and ask whether it matches God’s promises? [33:01]
2. Scripture trains the imagination to recognize God’s work even when it comes in unexpected forms. What recent small, concrete signs of God’s mercy or presence have you noticed (healed relationships, unexpected provision, changed desires)? Take two minutes now to name them aloud to the group. [35:19]
3. Waiting is formative, not passive. Which one habit from James — prayer over hurts, singing over joys, regular confession, asking elders to pray — is missing or weak in your life? What single, realistic step will you take this week to begin practicing that habit? Set a time and accountability. [38:28]
4. Capacity for patience grows from repeated, ordinary practices (learning to be bored on a road trip builds endurance). What “small training” could you adopt that would help you grow steadiness (a short daily fast, a five‑minute morning silence, a regular confession partner)? How will you start and how long will you try it before reassessing? [43:27]
5. Honest songs and psalms give language to faithful waiting (“How long, O Lord?”; “O come, O come, Emmanuel”). Which Advent carol or psalm will you use as your daily prayer this week? When each day will you sing or pray it, and how will you let it shape your longing for Christ? [46:02]
6. James urges the community to seek the wandering and restore those who have drifted. Who in your life needs a gentle outreach or a restoration conversation right now? What is one practical next step (a text, a visit, a prayer phone call) you will take in the next seven days? [39:56]