Jewish Thought

Up All Night, Wondering: Shavuot “Would You Rather?” Questions for All Ages 

 

There are a few times a year you might pull an all-nighter. 

Let’s start with the holiest one of all: On Shavuot night, many people stay up all night learning Torah. It’s said to be a tikkun (literally, a fixing or repair) for when the Jewish people overslept the day they received the Torah. 

But there are other reasons someone might stay up all night. Maybe they work long shifts. Maybe it’s the last night of camp, and they’re trying to soak it all in. Maybe they have a long flight across the world, with a stopover or two in between. 

Well, here’s another reason: you can stay up all night wondering a bunch of hypothetical questions and how you might respond to each one. 

Let’s do that! 

Here is a comprehensive list of “Would You Rather?” questions, Shavuot edition. Use them as springboards for discussion, as icebreakers at your yom tov meal or as something fun to think about as you’re falling asleep. (But be warned . . . they may keep you up all night!) 

Starting with dairy: 

• Would you rather be lactose intolerant during Shavuot or allergic to potatoes on Pesach? 

• Would you rather swim in a pool of sour cream or sleep in a bed made of soft cheese? 

• Would you rather accidentally sit on a slice of cheesecake or have someone accidentally sneeze on your slice of cheesecake? 

• Would you rather have to make fifty mini blintzes by hand or milk a cow every weekday for a month? 

Moving on to flowers: 

• Would you rather be a flower in a quiet field or a flower in a busy city window box? 

• Would you rather compete in a flower-arranging contest or a flower-themed scavenger hunt? 

• Would you rather discover a flower that changes color with your mood or one that glows in the dark? 

• Would you rather wear a flower crown every day for a week or memorize 300 names of flowers?

And now the Torah: 

• Would you rather know all of Torah by memory or be able to ask Hashem one question a day? 

• Would you rather witness a minute of Matan Torah or see the original luchot up close? 

• Would you rather travel back in time to meet your Torah-learning ancestors or forward in time to see how people will learn Torah in 100 years? 

• Would you rather watch a skilled sofer write out a whole parashah or listen to a talented ba’al korei lein one? 

And finally, the bigger, deeper, more thoughtful questions: 

• Would you rather be a leader like Moshe or have a leader like Moshe? 

• Would you rather have the ability to inspire one person every day with some Torah or have one life-changing Torah lesson taught to you once? 

• Would you rather be responsible for teaching Torah to the next generation or write a new Torah commentary that everyone studies? 

• Would you rather always remember the mitzvot perfectly or always feel motivated to learn something new about them? 

So, when Shavuot rolls around and it’s time for an activity or interesting discussion, you can whip out this list of questions and hear everyone’s creative responses, or you can stay quiet. What would you rather? :) 

 

Sari Kopitnikoff is an experiential educator, digital artist and content creator who is passionate about creating books, games, activities and shows that bring Judaism to life. You can find her books, games and lots of educational activities on her website, thatjewishmoment.com and on social media, @thatjewishmoment. 

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