(36) And He was also telling them a parable: "No one tears a piece of cloth from a new garment and puts it on an old garment; otherwise he will both tear the new, and the piece from the new will not match the old.  (37) And no one puts new wine into old wineskins; otherwise the new wine will burst the skins and it will be spilled out, and the skins will be ruined.  (38) But new wine must be put into fresh wineskins.  (39) And no one, after drinking old wine wishes for new; for he says, 'The old is good enough.' "   [Luke 5:36-39]

I've pondered over this passage for years now and prayed that the Lord would show me something to make sense of this.   What in the world does this mean?  Before, I always tried to make sense of the entire parable as one piece, but I think there are a few truths tucked in here that can be pulled out individually.  Then, maybe it will make sense as a whole.  Let's take it apart one verse at a time.

(36) And He was also telling them a parable: "No one tears a piece of cloth from a new garment and puts it on an old garment; otherwise he will both tear the new, and the piece from the new will not match the old. 

Jesus talks about sewing a patch on a piece of cloth.  From what I understand of cloth, once washed, it takes a new shape and loses a bit of its original color.  Once washed many times, it will eventually stop changing shape and size, but its color will continually fade with age.  So, if I were to sew a patch of new cloth on an old garment, the new would shrink and its color would begin to change after just the first washing.  Of course, the old garment would be already faded and shrunken from many washings.  The result would be a tearing away of the stitching between the patch and the garment.  Besides, the colors of the cloths would never likely match because the old garment has a head start on fading.  The two are different colors.

Likewise, characteristics of Christ cannot be placed upon an unregenerate man because the Holy Spirit would cause growth and change, tearing away from the old man.  A huge rift would be the result.  The two cannot be be sewn together.  Besides, they don't match.  There is no similarity in the appearance of the characteristics of the Spirit-filled man and the unregenerate man.  One is light, the other deeply dark.  Christlikeness must be placed on a changed, renewed man, who has been given a soft and supple heart, able to grow and change with the movement of the Holy Spirit.

(37) And no one puts new wine into old wineskins; otherwise the new wine will burst the skins and it will be spilled out, and the skins will be ruined.  (38) But new wine must be put into fresh wineskins. 

Wineskins, when new, are soft and supple leather -- able to accomodate the expanding gases emitted by the fermentation process.  Old wineskins, however, are brittle and hardened with time, not able to handle this expansion.  They would break if filled with new wine. 

Likewise, the old, dry, hard, brittle heart of unregenerate man is not able to handle the Holy Spirit coming in.  The Spirit comes in and cleans house, making radical changes in thought, word, deed, and desire.  He would burst the brittle unregenerate heart.  The Holy Spirit must move into a heart that he has been renewed, changed, made supple and soft, is ready for growth and change, and is able to accomodate expansion in love, compassion, and desire for the things of God.  The "new wine" of the Holy Spirit must be placed into "new wineskins", or a new heart.

(39) And no one, after drinking old wine wishes for new; for he says, 'The old is good enough.

Those accustomed to old wine, who have never tasted the new, are satisfied with what they have.  They have no desire for new wine because they don't even realize theirs is old and undesirable.  They are drinking what they are accustomed to, all they have, all they know ... the old wine.

Likewise, unregenerate man has never tasted the newness of life in Christ.  He knows nothing of it and has no desire to obtain it. He is satisfied with his sinful self and believes it is enough.  He has no idea his life and heart are bad or undesirable.

Praise God that He gives us new "patches" or desires, to sew onto new "garments" or our new, regenerated man.  He changes us from dark to light so that we match Him through the regeneration and sanctification processes.  Praise God that He gives us supple hearts (wineskins), into which to pour Himself (the new wine), so that we do not burst when He begins to change and grow us in the grace and knowledge of Christ!  Thank God that He does not leave us in that state of being satisfied with the old wine, for without the Holy Spirit's work, we would surely be drinking it now!

"Therefore if anyone is in Christ, he is a new creature; the old things passed away; behold new things have come."  (2 Corinthians 5:17)