“How can the guests of the bridegroom mourn ..." (Matthew 9:15)

“How can the guests of the bridegroom mourn while he is with them? The time will come when the bridegroom will be taken from them; then they will fast." (Matthew 9:15)

Why does Jesus tell this parable?

This parable is Jesus’ reply when John the Baptist’s disciples challenged the fact that Jesus’ disciples did not fast on a day they and the Pharisees fasted.

Jesus is responding to this:
Then John's disciples came and asked him, "How is it that we and the Pharisees fast often, but your disciples do not fast?" (Matthew 9:14)
Fasting in remembrance of a particular prophet or saintly teacher is an ancient custom among many traditional religious disciplines: This is why the Pharisees and John's disciples fasted on days to commemorate Prophets such as Moses, Abraham, or Jacob.

These traditions honor the representative of God or Prophet, often on their day of appearance (birthday) or disappearance (death of their body).

In much of the world, the appearance of Jesus is now celebrated as Christmas and his disappearance as Good Friday. In this case, scholars have determined that these dates do not correspond with Jesus' actual birth or death.  These dates were politically determined by the Roman Catholic institution to coincide with two secular holidays - the solstice celebrations and the beginning celebration of the Saxon idol Oestre or Eastre, respectively.

What does the parable of the bridegroom mean?

The word "guests" is a mistranslation of the Greek word υἱός (huios), which means, according to the lexicon, either a son (in the case of a family) or servant or follower (if not of the physical family - "used to describe one who depends on another or is his follower"). 

In fact, this is the same word translated to "son" in "son of God" and "son of man" along with other uses, such as "children of God" (Matt. 5:9), "your people" (Matt. 12:27), "people of this age" (Luke 20:34) and so on.

As such, "guests" would be an inappropriate translation. As mentioned above, the word relates to someone who is a servant or follower, not a "guest." The more appropriate translation would be "attendants" or "servants" of the bridegroom. This is similarly stated in the wedding parable.

In ancient times, large weddings were galas typically done by wealthy landowners who had servants and attendants. As the couple was married, these servants or attendants took care of things. Over the centuries this custom evolved into more of a family affair. But still even today we find that a groom will often have several "groomsmen" and the bride will have several "bridesmaids." 

Notice the word "maid" in the latter. This comes from the tradition of them being attendants or servants of the bride and groom.

This understanding is critical to the meaning because Jesus is comparing those who are the servants of a bridegroom during a wedding to those who are the servants of the spiritual teacher - the representative of God in Jesus' case.

The point Jesus is making here is that for Jesus’ disciples, Jesus is in the same role as representative of God that those previous prophets had been in. Jesus is stating that there was no need to “mourn” the passing of a prior representative of God if the disciples are in the service of a current representative of God - especially if that fasting interfered with their service.

The analogy is even more applicable when we consider the intimate relationship of love between Jesus and God. This concept of "bridegroom" illustrates a relationship between two persons - a relationship of love that exists between God and His representative.

While some might feel that this role of representative of God somehow diminishes Jesus’ stature or identity, quite the opposite is true. To be the authorized representative and servant of God is the highest position in the kingdom of God, as it relates to having an intimate devotional relationship with God. 

Jesus indicated this esteemed position of being a servant of God in many previous statements. For example:
"For I have come down from heaven not to do my will but to do the will of Him who sent me." (John 6:38)
“My teaching is not my own. It comes from the One who sent me." (John 7:16)
"The One who sent me is with me; He has not left me alone, for I always do what pleases Him.” (John 8:29)
These statements by Jesus reflect his self-identification as God's servant.

What is Jesus providing them?

For Jesus’ disciples, Jesus is their access and doorway to re-establishing their own relationship with God. Thus their focus, according to Jesus' statement, should be upon Jesus’ teachings so that one day they might also be prepared to serve and represent God.

This event also communicates the relationship that existed between Jesus and his teacher, John the Baptist. Why would John the Baptist's disciples challenge Jesus on how his disciples acted?

It is because Jesus was also a disciple of John the Baptist, evidenced by his baptism by John. So John's other disciples were seeing themselves as Jesus' peers. And thus they were wondering why Jesus did not follow the same practices with regard to fasting during the commemoration of previous prophets.

This, however, was a short-sighted understanding of Jesus' actual position. They obviously did not see Jesus' true exalted position as God's representative and loving servant.

Is this about honoring Jesus?

We can understand from this event that Jesus was one of John’s disciples. This is clear by Jesus' having traveled to the place where John was teaching, and by Jesus' eventual baptism by John.

We also know from this event that both the Pharisees and John’s disciples were observing the same religious holidays. We also know that Jesus and his disciples also observed these same holidays.

However, Jesus did not request from his disciples they fast. Why not?

Because they were traveling the (hot) countryside by foot and were doing God's service. He was teaching them to put their focus upon the practical matters of serving God. The ritual of observance by fasting was replaced by their practical service.

Jesus indicates here also that once he leaves the planet, his disciples should then honor his birth and death as the others were honoring the prophets before: with fasting.
"The time will come when the bridegroom will be taken from them; then they will fast."
The representative of God's appearance and disappearance should be honored with fasting, prayer and service. Currently many disrespect Jesus’ appearance and disappearance with a mad chase for materialism and commercialism. Both Christmas and Easter are typically celebrated with indulgence and a focus on materialism rather than a thoughtful day of fasting, worship and service.

On the day celebrated as Jesus’ appearance, the sectarian and secular worlds would rather honor a fat man in a red suit than honor God and His representative.

This is truly offensive to God and Jesus - who came to teach us to focus our lives upon God, not materialism. To use this day (Christmas) to celebrate materialism is truly a desecration. 

Jesus instructed his students to love God with all our heart and soul, and not love the world.