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St. Luke's version of the Beatitudes is significantly different than the much more famous version found in St. Matthew's gospel (Mt. 5: 1-12). First, in Luke's version, Jesus delivers them from level ground - in Matthew, he goes up a mountain. Matthew seems to invoke the image of these teachings coming from on high, evoking images of Moses receiving the 10 commandments on Mt. Sinai. For Luke, it seems that he is emphasizing that Jesus' teaching are accessible to all.
Secondly, the blessings (which begin with "blessed") are much more numerous in Matthew - he lists 9 - whereas Luke only has 4.
And of course, Luke adds the 4 woes as a contrast to the blessings - these woes are warnings to those who are too comfortable in their lives. As some scripture scholars say, Luke's version of the Beatitudes are meant to comfort the afflicted, and afflict the comfortable.
Try to place yourself into that scene 2000 years ago, on that level plain. There are many with you, all attentively listening to Jesus. You notice that as Jesus speaks, there are nodding of heads for the blessings, as well as shuffling of feet, eyes cast down for those for whom the woes "hit home". The question is, what is your reaction to what He says?