It's important to remember the religious/political environment Jesus was raised in. His mother and maternal grandparents, and therefore probably his entire family, were Essenes; Jewish messianic mystics and quasi-anarchists who resisted Roman rule, frequently with violence. The "insurrection" in which Barabbas allegedly murdered a Roman was an Essene uprising, as was the war which led to the famous mass suicide at Masada. The library at Qumron which contained the Dead Sea Scrolls was an Essene facility, and is believed to have been part of a network of similar caves storing food, weapons, clothing, and the wrtings of Essene teachers and holy men.
As a consequence, Jesus would have understood and appreciated the concept of "monkeywrenching," of causing small, irritating, time-consuming inconveniances to the Roman authorities...like what could happen if a someone carried a Legionairre's pack for two miles. He was also, of course, hostile to the Pharisaic ruling class, with whom the Essenes had a long-running and very nasty set of theological disputes. Forcing a Pharisee to immidiatly run off and take a Mikvah, a ritual bath ( as for instance by "flashing" them ) is the kind of prank which seems, to me, right up Jesus' alley.
You also have to remember that many of these things have a number of meanings. Your friend is correct about the slapping; in the strictly physical sense, it could be used as a means of insulting a Roman or other higher-ranking enemy. As a Jew, Jesus was ineligible for Citizenship, remember. It also has a linguistic meaning; the word used for "cheek," in this case, was an Aramaic word which also referred to a facet of one's personality. So while in the literal sense it can mean to expose your other cheek to an enemy's insulting blow, it could also be understood as showing your enemy a different side of yourself...which could mean opening a big ol' can of whoopass. Jesus wasn't opposed to such things; he did flog the merchants out of the temple, remember, and instructed his disciples to sell their cloaks to purchase swords.
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