Recall from our Chronology of Passion Week that Jesus ate the Passover meal with His disciples on Wednesday evening, was arrested that night, and crucified the following day, Thursday. Because the Jewish leaders reckoned the Passover to start a day later, Jesus’ death that afternoon occurred at the same time that their Passover lambs were being sacrificed. What day then must it have been that is referred to in Mat 26:17? In what sense was it the first day of Unleavened Bread? See Lev 23:5-6 and note that the Jews reckoned days to begin at evening, not at midnight as we reckon them; cf. Gen 1:5,8,13,19,23,31. Because the Jews had long been under the subjugation of the Romans who reckoned days as we do, the first day of Unleavened Bread that began Wednesday evening could also be thought of as happening that “day”.
What question did the disciples ask of Jesus? See Mat 26:17. Recall that Jesus had arrived at and been staying in Bethany, about two miles from Jerusalem (Joh 11:18) where Mary and Martha and Lazarus lived and where Simon the Leper had just hosted Him the previous Friday evening for the Sabbath meal. Considering that Mary and Martha’s family were of some means (recall that Mary had in her possession the alabaster vile of costly perfume worth a year’s salary, and had earlier hosted Jesus and His disciples in their home), why didn’t He just keep the Passover there? Cf. Deut 16:5-7 and notice that although Jesus and His disciples had been staying in Bethany, the Scripture indicates that during the festivals His custom was to stick even closer to Jerusalem, but would lodge on the Mount of Olives rather than in the crowded city. After leaving Bethany Monday morning it appears that He did not return there until after the resurrection; see Mar 11:11-12,19, 14:26,32, Luk 21:37, 22:39, 24:50; cf. Joh 8:1-2, 18:1-2, Act 1:12.
How did Jesus answer the disciples’ question about where to prepare the Passover? See Mat 26:18. What is meant by “a certain man”? Notice that the Greek word is used to refer to a person that one either cannot or does not wish to name. How many disciples did Jesus send into the city, and what additional information does Mark include that He gave to direct them on their errand? See Mar 14:13-16. Who does Luke say that the two disciples were? See Luk 22:8. As the city would have been very crowded for the festival and fetching daily water was a common household task, how would Jesus’ directions have helped guide them to their destination? Note: it was always a woman’s job, typically a young unmarried woman, to carry water, not a man’s; cf. Gen 24:11-13, Exo 2:16, 1Sa 9:11. Hence a man carrying a pitcher of water would have been very distinctive. What might finding a man humbling himself to do a woman’s job say about his character, and even that of his family, that would mark them as fit to support the nature of Christ’s kingdom? Cf. 1Pe 5:5.
What question did Jesus direct Peter and John to ask the master of the house after following the man with the water pitcher? See Mar 14:14. What does His question seem to indicate about some prior communication Jesus had with the house master about the room? Cf. Mat 26:18. What is meant by a guest room? Notice that it is the word used for a lodging place, and is the same word found in Luk 2:7 that Luke used for an inn. Hence, the room was likely more than just a dining room, but a place that the owner would rent out to accommodate travelers during the festivals. How else does Jesus describe the room, as it had perhaps been described to Him on another occasion, that would allow it to accommodate His retinue of disciples? See Mar 14:15. Where else in Scripture do we find mention of a large upper room in Jerusalem, that could easily have been the same room? See Act 1:13-15. Whose large house in Jerusalem do we later find that the disciples were accustomed to meet at when in Jerusalem for the feasts? See Act 12:4,12-16, and note that Mark was beloved by Peter, one of those whom Jesus sent to inquire about the room, and perhaps came to know the Lord through him; 1Pe 5:13. The early Church also believed that Peter was the source of much of Mark’s gospel material, and a significant portion of Mark’s gospel relates the events of Passion week to which he was likely a witness; cf. Mar 14:51-52 that some believe refers to Mark himself as it is only recorded in his gospel, and linen sheets were only possessed by those of affluence, of which Mark’s family appears to have been. It is therefore possible that the man carrying the pitcher was also Mark, whom Matthew left unnamed, perhaps both to respect his humility, and to protect his family from the unbelieving Jews who were becoming increasingly hostile to the followers of Jesus at the time he wrote.
 The New Manners and Customs of Bible Times; Ralph Gower.