Luke 5:33-39 Sermon for April 26, 2026

Good evening! Alright, so the passage we’re going to work through here is one that I must bring us through a couple of times so that you and I can really understand what’s happening here. What I’m going to do is read the passage all the way through once, and then I’m going to paraphrase it a bit as I give a ton of teaching.

If you have your Bible with you, turn with me to Luke 5:33-39. As a pastor, I’m using the CSB one. You are more than free to use a different translation, but in using the CSB, you might find it a bit easier to follow along. Here we go.

Luke 5:33-39 CSB

Then they said to him, ‘John’s disciples fast often and say prayers, and those of the Pharisees do the same, but yours eat and drink.’

Jesus said to them, ‘You can’t make the wedding guests fast while the groom is with them, can you? But the time will come when the groom will be taken away from them- then they will fast in those days.’

He also told them a parable: ‘No one tears a patch from a new garment and puts it on an old garment. Otherwise, not only will he tear the new, but also the piece from the new garment will not match the old. And no one puts new wine into old wineskins. Otherwise, the new wine will burst the skins, it will spill, and the skins will be ruined. No, new wine is put into fresh wineskins. And no one, after drinking old wine, wants new, because he says, ‘The old is better.’

Let’s break all of this down.

Now, remember, we’re just coming off the heals of Jesus hanging out with a bunch of tax collectors and all that jazz and the Pharisees were a bit annoyed by that. So, keep that in mind.

The Pharisees find another thing to get annoyed at and it’s the disciples of Jesus aren’t fasting when, in their mind, this is a big no no. So, they ask the questions of how come. Why are you guys not fasting. Why are you neglecting our tradition of fasting.

Let’s pause a moment. In the Old Testament, fasting was only required ONCE and it was during the Day of Atonement. Any other times of the year were voluntary. And people fasted for two reasons: First, to seek a deeper focus on the things of God. Second, they fasted as an expression of mourning.

It’s pretty simple understanding. The Pharisees, teachers of the Mosaic Law, come along and just create more unnecessary laws to begin with. In doing so, they said, “You must fast twice a week.” Not, “you can.” But, “you must.” And, in doing so, it served as a righteous enterprise that would so-call bring merit to the person who fasted.

Jesus rebukes the Pharisees  over and over again for these futile and demonic attempts at self-justification. The Pharisees were legalists and legalists legislate where God leaves people free. Again, they take, “you may” and turn it into “you must.”

Another prominent point of legalism is this idea that you can earn you way to heaven by obeying the law and doing good works. This is absolutely anti-gospel and must be rejected at all cost. These Pharisees were zealous, and there’s nothing wrong with being zealous if they are for the right things. But they weren’t zealous to conserve the law of God. They were zealous to of their own traditions.

And it’s worth distinguishing between good and right traditions versus made up ones. Good and right traditions are ones we see plastered in Scripture and ones routinely kept by the church over the last 2,000 plus years. Such as weekly worship, baptism, the Lord’s Supper, reciting the Lord’s Prayer, and all of that.

But the problem becomes when you make up traditions and demand they be kept or else. Like fasting twice a week. Or the thousands of traiditons churches have. IN fact, traditions that are made up can be really cool things but when they become traditions that must be honored and obeyed above the things of God and push people away, they become really bad things.

Alright, so, that’s verse 33. The Pharisees are annoyed, aggravated. And then Jesus basically asks, “What time is it, guys?” Let me explain.

The entire Old Testament is a foreshadowment of Jesus. It’s a redemptive timeline. All of these feasts and festivals and all that you see in the Old Testament were foreshadowing the Christ to come. They were all good things but not the final thing. Hebrews 10:4 says, “For it is impossible for the blood of bulls and goats to take away sins.” So, obviously, there’s something to come. What or who will take away sins?

Now, in the Old Testament, it’s been understood that Israel was the bride of God, so the New Testament church is the bride of Christ and Jesus is the bridegroom. Jesus is the bridegroom that has been promised for centuries now. And what Jesus is saying is that when the bridegroom is here, you don’t need to fast, you don’t mourn, and you don’t rend your garments.

What do you do? You rejoice! You throw a party! And when Jesus is referring to the bridegroom being taken away, he is referring to his execution and when Jesus departed, there was a great revival of voluntary fasting among Christians. Not mandated, but voluntary.

Really quick before going forward: The bridegroom, Jesus, is here and is the fulfillment of  the law and all things in the Old Testament. We see this as Jesus is the true Passover Lamb, the true High Priest, the true Temple, the true Atonement, the true Sabbath rest, etc.

With the presence of the bridegroom and going forward with the inauguration of the New Covenant, you’ll see that the ceremonial laws and dietary laws of the Old Testament are abrogated. They cease. In the Old Testament, the law was broken into three parts. The ceremonial, abrogated. The Dietary, abrogated, And then the moral law, still in place today.

In other words, while we can very much eat bacon today and buy clothes with multiple fabrics in them, it is still wrong to kill, abort, have sex outside of a marriage between a man and a woman, steal, lie, and all of that. When the church insists otherwise, that church ceases to become a faithful, true church. That church will be judged.

Ok, let’s move forward to this whole wineskins conversation that Jesus is referring to. Wineskins were made from either goatskin or sheepskin. It was made to keep and preserve good wine.

If a wineskin is old, it means that it’s been stretched due to fermentation of the wine. And eventually, the leather is stretched to it’s limit. If you put new wine into old wineskin, that’s already been stretched to its limit, the new wine will ferment and in the fermentation process the gases expand and stretch even further the wineskin. Well, since the old wineskin has already been stretched, what will now happen is that the wineskin will burst. You will lose the wineskin, therefore, you will lose the wine in the process.

Again, the basic idea of putting wine in new wineskin is to simply preserve the wine so you can carry it about and enjoy the wine. That’s it. To screw with the process is to potentially ruin the wine you were trying to preserve.

Ok, now, what in the world does this all mean? Well, Jesus is driving home a point here: You can’t just take the kingdom of God and the arrival of Jesus and just put it on top of the Pharisees’ traditions. It won’t fit! Something new is happening. Yes, this something new is built on the old, but it couldn’t be absorbed.

Let me explain it this way: you can’t just download Jesus into the Pharisees’ old religious system- it crashes the whole thing. The Kingdom of God isn’t an add-on update to their traditions; it’s a completely new operating system.

So, let’s sort of talk about two things here: first, let’s talk about trying to fit the New Covenant into the Old Covenant and why this doesn’t work.

The Old Covenant was temporary, preparatory, and foreshadowed Jesus. The New Covenant is a permanent, Spirit-powered, and built on Christ’s finished work. The Old Covenant system ran on law, priests, temples, sacrifices, and rituals. The New Covenant system runs on grace, the Spirit, Christ’s priesthood, and His once-for-all substitutionary atonement.

In the New Testament, you have Christ revealed. Everything in the Old Testament pointed to this. It talked about this. And then, it said, “Here I am!” And to make peace with God now, you are to profess and confess who Jesus is, what Jesus has done, and believe that Jesus is the only One who has done what is needed to make you at peace with a holy and righteous God. Jesus is God.

But, then let’s talk about the second thing here and it’s your life as a new creation. In keeping within the old and new wineskin analogy, you can’t have Christ and squeeze him into your old life and expect that to work.

Believe it or not, many churches teach this and they teach it by NOT teaching Christians the sanctification process of pursuing the holiness of God. They teach, “Yay, you’re loved by God now and now you have a ‘get out of hell card’ for life and just move on now.” No!

When you are born again, you are a changed person. It’s a process but change does begin immediately. The simple question of tonight is this: Has there been any change in your life through the power of the Holy Spirit, or are you still living the old way in the old wineskins? You see, you need new wineskin and this is the complete transforming work of the Holy Spirit in your life.

Let me take all of this and give you three quick things to walk away with:

First, when you are rooted in Jesus, there’s joy in the things you do and if there isn’t, it may be rooted in performance pressure.

Second, the gospel doesn’t fit inside a life built on earning, proving, or pretending. He doesn’t patch up the old me; He makes a new me.

Third, we are still fighting a sinful nature in us. We are constantly and naturally being drawn to what’s old and familiar, even if it’s broken and miserable. You need the Holy Spirit to help you.