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Bring on the tough stuff - there’s not just one right answer.
Who are we supposed to identify with more, Tevye or his daughters? Who do we sympathize most with? Is it different in each case? Are we meant to be nostalgic for a traditional arranged-marriage past or excited for the new love-based marriage future?
Why does Tevye constantly fall back on his Biblical quotations? Do they help him or others figure out what to do in a given situation? Are they a way to remove himself from something emotional? Is it simply a way to get superiority/authority over whoever he's arguing with? Is anyone ever impressed by his knowledge? If so, why? If not, why does he persist?
Okay, you've got your plans for a stage adaptation of Tevye greenlit. Now you have to decide what genre of stage performance it will be. An interpretive dance? An opera? A drama? A musical? Which parts of the stories would work best with which genres? What would you have to ditch in the adaptation process? Why?
Why do the stories end where they do? Why don't we follow Tevye and the rest of family into exile? How might Tevye change (or not) in a different environment? Does he adapt easily to new circumstances? How do you know?
Why did Sholem Aleichem make Tevye a dairyman? Why didn't he stay a very poor wood cutter? Why didn't the stories make him really wealthy (say, for example, through Menachem-Mendl's investments paying off or something)? Why a dairyman and not some other kind of trade—a guy with a general store, say, or one of the other businesses that he and Golde discuss opening?
Which jokes still land? Which don't you find funny? Which types of humor are less palatable these days (black humor? Jokes about violence? About women?) than a hundred years ago?
Which is the saddest of the daughters' stories? Which is the happiest? Why do you think so?