Matthew 26:36-38 - 36 Then Jesus went with them to a place called Gethsemane, and he said to his disciples, “Sit here, while I go over there and pray.” 37 And taking with him Peter and the two sons of Zebedee, he began to be sorrowful and troubled. 38 Then he said to them, “My soul is very sorrowful, even to death; remain here, and watch with me.”

Hebrews 4:15 - For we do not have a high priest who is unable to sympathize with our weaknesses, but one who in every respect has been tempted as we are, yet without sin.

Jesus invites us to bring our sorrow to God honestly.

Matthew 26:39-44 - 39 And going a little farther he fell on his face and prayed, saying, “My Father, if it be possible, let this cup pass from me; nevertheless, not as I will, but as you will.” 40 And he came to the disciples and found them sleeping. And he said to Peter, “So, could you not watch with me one hour? 41 Watch and pray that you may not enter into temptation. The spirit indeed is willing, but the flesh is weak.” 42 Again, for the second time, he went away and prayed, “My Father, if this cannot pass unless I drink it, your will be done.” 43 And again he came and found them sleeping, for their eyes were heavy. 44 So, leaving them again, he went away and prayed for the third time, saying the same words again.

Luke 22:44 44 And being in agony he prayed more earnestly; and his sweat became like great drops of blood falling down to the ground.

Matthew 6:7 - “And when you pray, do not heap up empty phrases as the Gentiles do, for they think that they will be heard for their many words.”

Luke 18:1 - And he told them a parable to the effect that they ought always to pray and not lose heart.

It is not our words or the repetition of our words that gives power to prayer, rather it is the God to whom we pray who answers prayer according to His will.

Matthew 20:22-23 - 22 Jesus answered, “You do not know what you are asking. Are you able to drink the cup that I am to drink?” They said to him, “We are able.” 23 He said to them, “You will drink my cup, but to sit at my right hand and at my left is not mine to grant, but it is for those for whom it has been prepared by my Father.”

Isaiah 53:5 - 5 But he was pierced for our transgressions; he was crushed for our iniquities; upon him was the chastisement that brought us peace, and with his wounds we are healed.

Hebrews 12:17-18 - 17 Therefore he had to be made like his brothers in every respect, so that he might become a merciful and faithful high priest in the service of God, to make propitiation for the sins of the people. 18 For because he himself has suffered when tempted, he is able to help those who are being tempted.

Matthew 26:30-35 - 31 Then Jesus said to them, “You will all fall away because of me this night. For it is written, ‘I will strike the shepherd, and the sheep of the flock will be scattered.’ 33 Peter answered him, “Though they all fall away because of you, I will never fall away.” 34 Jesus said to him, “Truly, I tell you, this very night, before the rooster crows, you will deny me three times.” 35 Peter said to him, “Even if I must die with you, I will not deny you!” And all the disciples said the same.

Spiritual laziness can leave us unprepared for trials and temptation.

Matthew 26:45b-46
See, the hour is at hand, and the Son of Man is betrayed into the hands of sinners. 46 Rise, let us be going; see, my betrayer is at hand.”

Application:
1. Pray Honestly
2. Pray Vigilantly
3. Pray with Surrender

Discussion Questions

1. Jesus said, “My soul is overwhelmed with sorrow to the point of death.” Have you ever felt something similar—deep emotional or spiritual distress? How did you respond in that moment?

2. How does it impact you to know that Jesus fully experienced human emotions like anguish, grief, and anxiety?

3. Why is it important that Jesus shared his sorrow both with God and with his closest friends? What does that say about the role of community and vulnerability in our spiritual lives?

4. Jesus prayed the same thing three times. What does this teach us about persistence in prayer?

5. Have you ever struggled between wanting God’s will and wanting something else for yourself? How do you process that tension?

6. What might “the cup” represent in your life right now—a situation or burden you wish would pass, but may be part of God’s will for you?

7. Jesus told them, “The spirit is willing, but the flesh is weak.” How have you experienced that tension in your own spiritual life?

8. What spiritual habits can help us stay awake and vigilant in our walk with God—especially in hard seasons?

9. Jesus didn’t leave the garden with a changed circumstance, but with changed resolve. Have you ever had a moment where prayer didn’t change the situation, but it changed you?

10. How do you typically respond when God’s answer is “no” or “not yet”? What helps you trust His will in those times?

11. What does it mean for us to pray, “Not my will, but yours be done” in everyday life—family, work, church, or major life decisions?

12. What one step can you take this week to practice honest prayer, faithful surrender, or spiritual vigilance?