When the dark night comes… (Matthew 26:31-46)


è What was the longest night of your life: teen sleepover, pregnancy, work, conversation with a friend, a bad circumstance? What role did prayer play in this long night?

è Describe recent crisis in your life in which you went to God in prayer? What impact did prayer have on you and the crisis you encountered?

Our study today focuses on Jesus’ prayer in the most challenging crisis of His being betrayed, unjustly trialed and persecuted, tortured, and crucified. Like Jesus, we can identify God to sustain us through prayer.

EXAMINE           Matthew 26:31-46

When dark nights come, we must be prepared (Matt 26:31-35).
Jesus knew He was in for a long and dark night. Jesus tells the disciples they will fall away from Him. His message quotes Zechariah 13:7 to show His actions and surrounding circumstances fulfill OT Scripture, characteristic in Matthew’s Gospel. While Jesus prophesies about His crucifixion, He also promises His resurrection (cf. Mat 16:21; 17:9, 23; 20:18-19).

Peter cannot fathom and will fight against any plot to foil Jesus’ plans for being king. While His pride is admirable, it is also arrogant to dismiss Jesus’ words and not to consider his weakness or selfishness. Peter’s bold absolute statements would later cause grief and repentance (Mat 26:75).

The Jews divided the night into four parts: evening, from 6-9pm; midnight, 9pm-12am; cock crow 12am-3am; and morning, 3am-6am. The third period gained its name from the fact that roosters began to crow about the end of that period and continued to crow periodically until after daybreak.

è What difference does it make that Jesus does not appear surprised by His dark night? How could/should that relate to us today in our dark nights? How can we prepare for crisis (cf. James 1:2-6)?

è How was Peter’s promise both admirable and arrogant? When have you made a sincere promise, but failed to follow through with keeping it?

è In your relationship with Jesus, have you ever spiritually heard a rooster crow? How was that resolved?

When dark nights come, we need to pray (Mat 26:36-44).
Jesus had a favorite place to pray (Jn 18:2). In Galilee, Jesus went to a nearby mountain, often spending the entire night in prayer. At other times, Jesus withdrew into the wilderness or a remote place for privacy and personal prayer. In this instance, it was the garden of Gethsemane.prayer_1

Gethsemane refers to oil press; the pressing and crushing of olives or grapes to produce the oil or wine. Charles Spurgeon says, “The wine is not made by gathering the clusters, but by treading the grapes in the wine-vat: under pressure the red juice leaps forth.” The beauty and blessing of wine only comes through the grinding of the grapes. On this night, Jesus would be pressed to full capacity, with glimpses of the cross leading to the glory of the resurrection.

Jesus prayed because He was sorrowful (λυπέω) and troubled, saying, “My soul is very sorrowful (περίλυπος = sorrow all around, surrounded by sorrow), even to death”. In this dark night, Jesus can identify with our sorrows and sadness (Heb 4:15).

Surprising upside gifts of sadness[1]

1)    Sadness forces me to depend on Jesus

2)    Sadness gives me humility and empathy

3)    Sadness rescues me from silliness/ontological lightness

4)    Sadness prepares and strengthens me for future struggle & to be a spiritual giant;

è Where is your spiritual Gethsemane? Do you have a specific place or habit of prayer?

è How do you think the disciples felt listening to Jesus’ prayer confessions?

è How can Jesus’ admission of deep sorrow and depression be both misinterpreted and comforting by believers today? What do you appreciate most about Jesus’ emotions in this narrative?

è Why is prayer often a last resort rather than priority? What can we do to remember that prayer is a worthy action in time of trouble?


When dark nights come, we need partners (Mat 26:36-44).
Jesus prayed with the disciples nearby, instead of isolating Himself. He brought all the disciples but instructed them to sit while He went deeper into the garden. However, Jesus did ask Peter, James and John to go along with Him to pray. Yet, there were moments Jesus left even the 3 to pray alone. It seems Jesus prayed with the disciples present for both companionship and instruction for how to endure a dark night of the soul.

è Do you think the disciples felt Jesus played favorites since some stayed but others were taken closer with Jesus to pray? Was Jesus’ selection of these disciples indicative of their spiritual maturity or immaturity needing further shaped?

è What is the benefit of praying with other believers?

o   Me w/ Bayside prayer meetings, Pastor Carl Jennings @SC, SamDutton, Villafuerte, Voelp… others.

o   Who would you want to “watch and pray” with you during a dark night?

è How can our group better balance time in relevant study and time in relational prayer?

o   Prayer dynamics: 1) Group requests, 2) Partner experiences, 3) Silent Prayer

o   What if… 1x month met in house for prayer fellowships?


When dark nights come, we need to trust and obey (Mat 26:41-46).
Jesus’ night of prayer reflected His dependence on God the Father. He submitted to the Father’s will and not His own. In Jesus humanity, He sought alternate plans but trusted the Father’s purpose. Jesus’ conversation in prayer with the Father is a profound marvel to us. Likewise, we see Jesus’ obedience and are moved by His sacrificial love for us to drink the cup of God’s wrath on our sin (cf. Ps 75:8; Isa 51:17; Jer 49:12).

Looking backwards, we look down on the disciples’ lack of attention and sleepiness during Jesus’ dark night. Jesus confronts them at least three times (26:40, 42, 44). Jesus appears gracious recognizing “the spirit indeed is willing, but the flesh is weak” (26:41).

After Jesus had prayed through the night, He knew the hour had arrived from Him to fulfill God’s mission to be betrayed, trialed, and crucified. He faced the dark night with faith and courage, saying, “Rise, let us go!”

è What does Jesus’ submission reveal about His relationship to the Father? (Trust, varied roles in Trinity)

There is a difference between “Oh my God” and “O my God”.[2]

è How does faith and trust foster courage in our circumstances?

è What are the consequences when Christians “fall asleep” during the mission?

è What can we do to avoid physical exhaustion and spiritual failure?

o   1Peter 5:6-10 “Humble yourselves under the mighty hand of God, so that at the proper time he may exalt you, casting all your anxieties on him, because he cares for you. Be sober-minded; be watchful. Your adversary the devil prowls around like a roaring lion, seeking someone to devour. Resist him, firm in your faith, knowing that the same kinds of suffering are being experienced by your brotherhood throughout the world. And after you have suffered a little while, the God of all grace, who has called you to his eternal glory in Christ, will himself restore, confirm, strengthen, and establish you.”



Crisis are God’s means to bring about growth and glory.

Pray with hope.


[1] https://www.thegospelcoalition.org/article/the-surprising-upside-to-sadness

[2] https://www.esv.org/search/?q=%22o+my+god%22

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