Our question for Luke 5 is: “What does the parable of the wineskins mean? I’m not a wine connoisseur, but isn’t old wine supposed to taste better than new wine?”

The short answer is: Jesus is saying that he’s introducing something new, and it bursts through the old way of doing things. The problem, of course, is that people who are used to the old way of doing things don’t want to change, even if the new is better. They like things the way they are, the status quo.

But there’s more context to this parable than we often pay attention to.

For example, since our Bibles have subheadings that break up conversations, we often miss that Jesus told this parable at a large (and probably rambunctious!) dinner party (v. 29). He’s drawing an illustration from what’s literally happening around them – eating and drinking.

He’s also continuing a conversation that started a few verses before this (v. 30). The Pharisees say to his disciples (not to him, mind you!): “why do you eat and drink with tax collectors and sinners?”

In the old way of doing things, there are the “good guys” and the “bad guys”. Not surprisingly, the “good guys” are upset that Jesus, a rabbi, is hobnobbing with the “bad guys.” (Although it’s interesting to note that the Pharisees are apparently at this party too!)

Jesus himself responds to them, and there’s some back and forth. In particular, the Pharisees are confused because Jesus and his disciples are eating and drinking, as opposed to the disciples of John the Baptist and of the Pharisees, who fast and pray. Aren’t religious disciples supposed to do religious things like fast and pray?! 

(As a side note, notice that “disciples” are a common thing in this culture and era. The Pharisees had them; John the Baptist had them. Jesus calls his first disciples in this chapter, and they leave everything to follow him, but that’s apparently something that people did. You might say that the disciples are the roadies of the first century – or perhaps we should more accurately say that roadies are disciples of the band they follow!)

But Jesus is doing something different from the religious expectations. He’s caring for the outcasts. He’s offering healing and hope to the sinners, rather than shunning them because they have broken the Law (which is what a “good” religious person would do under the old way of doing things).

Jesus is wooing his bride. He’s wooing her away from a slave master – the Law. He’s wooing her to something new. He’s wooing her to a sweet marriage, based on love, not Law. (Hosea 2, Revelation 19:9)

And when a Bridegroom is wooing his bride, it doesn’t usually involve fasting! It involves wining and dining, new clothes (v. 36), celebrating the start of something new. The old wine is only appealing because of the comfort of familiarity. But the new wine is healing, hope, celebration, adventure, love.

All this, then, begs two questions of us: Are you hanging with the Pharisees, drinking the old wine of your “good person” status (v. 31)? Or are you allowing Jesus to woo you away from your “filthy rags of self-righteousness” and drink the new wine of the new Kingdom, where Jesus is our kingly Bridegroom?

“Behold, I am doing a new thing… Behold, I am making all things new.” (Isaiah 42:9; 43:19; 48:6; 65:8-10, 17-25; Jeremiah 31:31-34; Ezekiel 11:18-20; 18:31; 36:25-27; Zechariah 9:16-17; Revelation 21:1-5)