The disciples probably left Jesus alone because of His weariness, but if they had been there the conversation with the Samaritan woman could never have been started in the way it was.  Indeed, she may never have approached the well until the band of travelers had left and even if she had, Jesus would probably not have embarrassed her in front of others with an account of her sins.  Jesus used the opportunity to draw the woman into a conversation that would result in salvation. Godet remarks, “He is not unaware that the way to gain a soul is often to ask a service of it.” (qt’d in Morris p. 258)

Jesus probably had at least 2 reasons for sending all of His disciples into town to buy food. The first was that Jesus may have already known that the woman was going to be there and wanted to meet her needs by having His disciples gone. (How could Jesus have known this?) The second is for the disciples themselves. Following Him had already produced some rather spectacular results, for it is unlikely that they would have bought food from the Samaritans before having been with Jesus. In fact, the Jews contemptuously called the Samaritans Cuthaeans after one of the Gentile peoples who the Assyrians had populated the country with and one of the sayings of the Jewish rabbis was, “Let no man eat of the bread of the Cuthaeans, for he who eats their bread is as he who eats swine flesh.” (qt’d in Barclay) Jesus sent them to town as a stretching time to break down barriers within them.

Travelers would have carried with them a skin-bucket for drawing water, but the disciples had obviously taken it with them into town. Jesus was thirsty and had no means of drawing water from a deep well. What He was asking was for her to draw water in her container and let Him drink from it.  A Pharisee would rather have died of thirst than defile himself in such a manner, but not Jesus! He saw everyone as equal and loved them as they were.