Watch and Pray

The Power of Practice

Well, good morning, Well Community Church. How are we doing this morning? I am super excited to be hanging out with you guys. If I haven’t met you yet, my name is Matt. I’m one of the campus pastors on staff. I oversee our 7:00 PM gathering on Sunday nights, and I’m thrilled to be here with you this morning.

As I think about my time at this church, I just love the process of what we do here week in and week out—taking a book of the Bible and going line by line through the text. During the summers, we do something a little different. we pull out of our regular series and enter into a gospel-centered series. This summer, we are looking at a series called Invitation. We’re going through the life of Jesus, looking at different invitations he gave—not only to those in the original context but to us as the modern-day church. How do we take these invitations and walk intimately and dependently on Jesus?

This morning, we are going to unpack an invitation found in the Gospel of Matthew. If you have your Bibles, open up to chapter 26.

Matthew 26:36-41 (NASB)

Then Jesus came with them to a place called Gethsemane, and said to His disciples, ‘Sit here while I go over there and pray.’ And He took with Him Peter and the two sons of Zebedee, and began to be grieved and distressed. Then He said to them, ‘My soul is deeply grieved, to the point of death; remain here and keep watch with Me.’ And He went a little beyond [them], and fell on His face and prayed, saying, ‘My Father, if it is possible, let this cup pass from Me; yet not as I will, but as You will.’ And He came to the disciples and found them sleeping, and said to Peter, ’So, you [men] could not keep watch with Me for one hour? ‘Keep watching and praying that you may not enter into temptation; the spirit is willing, but the flesh is weak.’

What we see here is Jesus, moments before he goes to the cross to take on the sin of the world. He enters intimately, honestly, and submissively before the God of the universe. He is in a moment of deep agony as he begins to taste what is to come. And he doesn’t enter into that prayer on that mountainside by himself; he invites three of his closest friends, his inner circle, to hold that space with him and invites them into the process.

Now, if you were to spend any amount of time with me, you would notice that I have a deep, unhealthy obsession with the sport of basketball. I grew up playing in high school and college. I remember back in 2009, watching the NCAA tournament and being introduced to a small, six-foot-three point guard named Steph Curry. When he was drafted by the Golden State Warriors, he became my favorite player. He wasn’t overly dominant physically, but he could shoot the lights out of the ball.

I was glued to my TV during the 2024 Olympics, watching the United States make their gold medal run. In the final against France in Paris, the game was going wire-to-wire. With about a minute left, the U.S. was up by six, but it felt like a fragile lead. France was making a run. Then, the ball finds its way into Steph Curry’s hands. With the shot clock ticking down, he takes a dribble, gets double-teamed by two guys who are at least 6’9“, does a behind-the-back move, steps back three feet behind the line, and—while falling out of bounds—launches a shot. Time stood still. You could hear a pin drop. Then, swish. One of the greatest shots of all time.

I lost my mind in my living room. To the untrained eye, it looked like the luckiest shot in history. But a few months later, in a documentary, Steph said something profound. He said, “I have been practicing that shot for years. In gyms where nobody knew who I was, I practiced that shot again and again and again.” He said that in the heat of battle, his mind turned off and it became muscle memory. He knew it was going in.

In the same way, Jesus is inviting us to a practice, a discipline, and a consistent entering into the spiritual practice of prayer. This discipline forms us into the kinds of people who can respond like Jesus. At first, it will seem unnatural, but over time it becomes muscle memory, even in the face of weakness and temptation.

The Weight of the Garden

Look at verse 36 with me. It says, “Then Jesus…” Now, I promise I’ll go faster than two words at a time, but that word “then” is important. It implies a series of events happened before we got here. So, what happened? If you rewind the tapes to earlier in the chapter, you’ll see Jesus in an upper room with his twelve disciples.

Matthew 26:20 (NASB)

Now when evening came, Jesus was reclining [at the table] with the twelve disciples.

He is sharing the Passover meal with them, a meal they had known since they were kids. But Jesus redefines the weight of that meal. He tells them he is fulfilling it and marching them into a greater exodus—not from human slavery, but from the spiritual oppression of sin and death. He tells them his body will be broken and his blood shed for the forgiveness of sins.

Then Peter, who has a propensity for sticking his foot in his mouth (something I deeply identify with), stands up and says, “I would never let that happen to you! I’d rather die in your place!” Jesus looks at him lovingly and says, “Peter, you’re going to deny me three times tonight.” Then he looks at the rest of the group and tells them they will all desert him. The tension in that room was so thick you could cut it with a knife. That is the aftermath we walk into in the Garden of Gethsemane.

Jesus retreats to a mountainside called Gethsemane, which means “olive press.” It was a grove where olives were crushed by a giant stone to produce oil. In a garden marked by pressing, Jesus is being pressed by the weight of the sin of the world. He takes Peter, James, and John with him and displays a vulnerability they had never seen. He is grieved to the point of death. He is in physical, spiritual, and emotional agony. He asks his friends to simply “watch” with him—to stay awake and be fully present.

An Intimate Father and an Honest Request

How does Jesus respond to this pressure? He prays.

Matthew 26:39 (NASB)

And He went a little beyond [them], and fell on His face and prayed, saying, ‘My Father, if it is possible, let this cup pass from Me; yet not as I will, but as You will.’

Jesus starts his prayer by saying, “My Father.” This gives us a keyhole view into the God Jesus knew. He didn’t know a God who was passive or distant. He knew a Father who was deeply intimate, deeply loving, and always available. Because of that intimacy, Jesus could make an honest, vulnerable request: “If it is possible, let this cup pass from me.”

In the Bible, the “cup” usually symbolizes judgment. Jesus is tasting the judgment he is about to endure, and as a Son, he asks if there is another way. He isn’t trying to sidestep the goal of redeeming creation; he’s asking about the method. But then he prays the most profound statement known to man: “Yet not as I will, but as you will.”

Think about the contrast. In Genesis 3, the first man, Adam, stood in a garden and said, “God, not your will, but mine.” The result was sin and death. But here, Jesus stands in a garden and says, “Father, not my will, but yours.” Tim Keller said the victory of Calvary started in this olive grove. This was the battleground. The cross and the grave were the knockout punch, but the war was won when Jesus submitted his will in prayer.

The Weakness of the Flesh

Jesus arises from prayer to check on his friends, and what does he find? They are dead asleep. They are knocked out.

I experienced the weight of this in my own life recently. Three months ago, my wife and I welcomed our third child. My wife is a rockstar—three kids, three C-sections—she’s Wonder Woman. After the birth, we got to our room, and I told her, “I’m staying up. You need to rest. I am not going to sleep.” I had all the willpower and incentive in the world.

I lay down on the couch for “just one minute” to rest my eyes. I woke up an hour later to my wife yelling my name. She said, “I’ve been yelling for an hour! I thought you might have died!” In that pivotal moment, no matter how much chutzpah I had, I couldn’t stay awake on my own strength. The disciples were the same way. They had the best of intentions, but they couldn’t follow through.

Romans 7:19 (NASB)

For the good that I want, I do not do, but I practice the very evil that I do not want.

As Paul says, the good we want to do, we don’t do. The desire is there, but the storehouses of strength are empty. Jesus tells the disciples, “The spirit is willing, but the flesh is weak.” He isn’t talking about the Holy Spirit here; he’s talking about the human spirit—our will and our passion. Following Jesus on your own strength is like trying to lift a heavy weight while you’re sick as a dog in bed. It’s impossible.

Watching and Praying

Have you ever felt that way? You have the desire to love your neighbor, but then you pull into your garage and close the door. You have the desire to stop gossiping, but you find yourself at the water cooler doing it again. You white-knuckle your way through a habit, only to fall back into it two minutes later.

Jesus doesn’t look at you and say, “Just try harder.” He invites you into dependence. He says, “Watch and pray.”

To “watch” means to stay alert—not just to what is happening around you, but to who is with you. It’s about abiding. We live in an age where we are distracted into oblivion. If you don’t believe me, check your screen time. I think the enemy’s main strategy today isn’t necessarily to make you blow up your life in sin; it’s to lull you to sleep. He’s fine with Jesus being in the room as long as your attention is elsewhere.

Prayer is the practice that keeps our gaze on Him. Dallas Willard defined a spiritual practice as any activity within our power that enables us to do what we cannot do by direct effort. I cannot force myself to be a person who loves like Jesus, but I can engage in prayer. I can say, “God, I can’t, but you can.”

Spiritual Muscle Memory

Through prayer, the Holy Spirit takes what is unnatural—dependence on God—and turns it into muscle memory. Over decades, it becomes natural to follow Him in every season.

1 Thessalonians 5:16-18 (NASB)

Rejoice always; pray without ceasing; in everything give thanks; for this is God’s will for you in Christ Jesus.

When I first read that, I felt shame. “Pray without ceasing? I can’t do that!” But this verse is more about God’s character than our performance. It tells us that God is constantly available. We have unhindered access to Him at all times.

Sometimes prayer looks like being on your knees in a quiet room. But for me, in this season—finishing a Master’s degree, moving houses, raising a newborn—prayer looks different. It’s getting in the car and saying, “God, I invite you into this drive.” It’s going to the grocery store and saying, “God, I invite you into this trip.” I’m not inviting Him to a place where He isn’t; I’m inviting my soul to the reality that He is already there.

Learning from the Model

Jesus doesn’t just give us an invitation; he gives us a model. He enters intimately as a Son. He is honest about his pain. Prayer isn’t a place to be perfect; it’s a place to be real. If you don’t have the words, that’s okay. God doesn’t need you to get your vernacular together before He’ll listen. If my six-year-old comes to me crying and rambling, I don’t tell him to go fix his thoughts and come back. I just hold him.

When you don’t know what to pray, use the handles God gave you. Use the Psalms.

Psalms 51:1-19 (NASB)

For the choir director. A Psalm of David, when Nathan the prophet came to him, after he had gone in to Bathsheba. Be gracious to me, O God, according to Your lovingkindness; According to the greatness of Your compassion blot out my transgressions. Wash me thoroughly from my iniquity And cleanse me from my sin. For I know my transgressions, And my sin is ever before me. Against You, You only, I have sinned And done what is evil in Your sight, So that You are justified when You speak And blameless when You judge. Behold, I was brought forth in iniquity, And in sin my mother conceived me. Behold, You desire truth in the innermost being, And in the hidden part You will make me know wisdom. Purify me with hyssop, and I shall be clean; Wash me, and I shall be whiter than snow. Make me to hear joy and gladness, Let the bones which You have broken rejoice. Hide Your face from my sins And blot out all my iniquities. Create in me a clean heart, O God, And renew a steadfast spirit within me. Do not cast me away from Your presence And do not take Your Holy Spirit from me. Restore to me the joy of Your salvation And sustain me with a willing spirit. [Then] I will teach transgressors Your ways, And sinners will be converted to You. Deliver me from bloodguiltiness, O God, the God of my salvation; [Then] my tongue will joyfully sing of Your righteousness. O Lord, open my lips, That my mouth may declare Your praise. For You do not delight in sacrifice, otherwise I would give it; You are not pleased with burnt offering. The sacrifices of God are a broken spirit; A broken and a contrite heart, O God, You will not despise. By Your favor do good to Zion; Build the walls of Jerusalem. Then You will delight in righteous sacrifices, In burnt offering and whole burnt offering; Then young bulls will be offered on Your altar.

One of the lynchpin moments in my story was praying Psalm 51 in tears. We also have the model Jesus taught his disciples.

Matthew 6:9-13 (NASB)

’Pray, then, in this way: ’Our Father who is in heaven, Hallowed be Your name. ’Your kingdom come. Your will be done, On earth as it is in heaven. ’Give us this day our daily bread. ’And forgive us our debts, as we also have forgiven our debtors. ‘And do not lead us into temptation, but deliver us from evil. [For Yours is the kingdom and the power and the glory forever. Amen].’

In the garden, Jesus prayed, “My Father.” In the Lord’s Prayer, he taught us to say, “Our Father.” In the garden, he prayed, “Your will be done.” In the Lord’s Prayer, he taught us to pray, “Your kingdom come, your will be done.” He modeled the dependence he wants us to practice.

As we close, we’re going to do a little “lecture and lab.” We’re going to pray the Lord’s Prayer together. Don’t let the enemy wrap you in shame about your prayer life. This is an invitation to a God who is lavishly generous with His Spirit. He wants to strengthen you. He wants to take that dependence that feels so unnatural right now and, over time, make it the most natural thing in your life.

Let’s pray together.

Our Father, who is in heaven, hallowed be your name. Your kingdom come, your will be done, on earth as it is in heaven. Give us this day our daily bread, and forgive us our debts, as we also have forgiven our debtors. And do not lead us into temptation, but deliver us from evil. For yours is the kingdom and the power and the glory forever. Amen.