Luke 5:27-39

27 After this, Jesus went out and saw a tax collector by the name of Levi sitting at his tax booth. “Follow me,” Jesus said to him, 28 and Levi got up, left everything and followed him.

29 Then Levi held a great banquet for Jesus at his house, and a large crowd of tax collectors and others were eating with them. 30 But the Pharisees and the teachers of the law who belonged to their sect complained to his disciples, “Why do you eat and drink with tax collectors and sinners?”

31 Jesus answered them, “It is not the healthy who need a doctor, but the sick. 32 I have not come to call the righteous, but sinners to repentance.”

33 They said to him, “John’s disciples often fast and pray, and so do the disciples of the Pharisees, but yours go on eating and drinking.”

34 Jesus answered, “Can you make the friends of the bridegroom fast while he is with them? 35 But the time will come when the bridegroom will be taken from them; in those days they will fast.”

36 He told them this parable: “No one tears a piece out of a new garment to patch an old one. Otherwise, they will have torn the new garment, and the patch from the new will not match the old. 37 And no one pours new wine into old wineskins. Otherwise, the new wine will burst the skins; the wine will run out and the wineskins will be ruined. 38 No, new wine must be poured into new wineskins. 39 And no one after drinking old wine wants the new, for they say, ‘The old is better.’

An Enigma

I have read Luke 5:27-39 numerous times over the last 10 years. Each time I read it, I was struck by an enigma which niggled me to no end.

The scripture essentially describes a conversation that took place between Jesus and the Pharisees over the topic of fasting. They took issue with Jesus feasting with sinners and tax collectors; they thought that He and His disciples ought to have been fasting instead.

Jesus answered them saying that whilst He was with them, they should be feasting, not fasting. People often fast to get close to God, but He was right there with them already, so there was no need to fast (at least, not until He was taken away back to Heaven). In other words, to fast would mean missing out on rejoicing with Him and not making the most of His presence.

Furthermore, the people that were with Him were sinners who had come to repentance - so that's another important reason to feast and celebrate (just as the angels in heaven would be doing - Luke 15:7,10).

Jesus then proceeded to give a parable about new and old garments, old wineskins and new wine. This baffled me greatly, in two ways:

1. What have old and new garments, old wineskins and new wine have to do with fasting?

2. Why use garments, wineskins and wine specifically, when He could have used so many other objects to illustrate His point about fasting? 

There are, of course, numerous articles and sermons on the Internet regarding this subject. However none that I had read or listened to managed to satisfactorily answer the questions I had. They didn't quite hit the mark, and I felt there was something deeper that was being missed.

So I asked the Lord the above two questions. After 10 years of asking, the answers finally came this January 2025! The answers were so simple, though nothing short of brilliant (as one would expect from God) - which I shall now share with you.