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In Bava Metzia 84a, we learn about Reish Lakish and the 24 questions he asks.

After hearing this story I was inspired to ask more questions. I'm struggling with being inquisitive. I'm just taking my learning in without issue unless I really don't understand something or it "rivals" some other awareness.

So how do you come to ask 24 questions on a topic? Is there a book or shiur that addresses this handicap?

  • I would emphasise more clearly that you are only looking for sources, not personal opinions. Otherwise, this seems primarily opinion based. (Even still it is arguably primarily opinion based). – mevaqesh Feb 17 '17 at 21:57
  • If you arent encountering difficulties, that isn't necessarily indicative of a lack of inquisitiveness, you might just be presented with decent explanations of the subject matter. Do you know that you lack inquisitiveness. – mevaqesh Feb 17 '17 at 21:59
  • If the problem is that you generally lack the trait of inquisitiveness, is there any reason to assume that this is a question about Judaism? Consider asking it on productivity.stackexchange.com. – mevaqesh Feb 17 '17 at 22:01
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The following is how Soncino (correctly) translates the relevant portion of the story:

'Are you as the son of Lakisha?' he complained: 'when I stated a law, the son of Lakisha used to raise twenty-four objections, to which I gave twenty-four answers, which consequently led to a fuller comprehension of the law; whilst you say, "A Baraitha has been taught which supports you:" do I not know myself that my dicta are right?'

While the Aramaic word is קושייתא, which means questions, the true meaning here is not inquisitiveness. Resh Lakish was not trying to find out more details or to understand the depth of the reasoning of the law.

Rather, Resh Lakish had been arguing with Rabbi Yochanan. The 24 kushyasa were 24 objections. Resh Lakish had mastered the Tannaitic material, and when Rabbi Yochanan stated a law, Resh Lakish argued that this law did not accord with this source or that that source. In response, Rabbi Yochanan had to explain how each of these sources was different from his case. In contrast, Rabbi Eleazar ben Pedat found a support rather than a contradiction in the Tannaitic material. Rabbi Yochanan yearned for someone to argue with.

While inquisitiveness can indeed be a positive trait, this is not necessarily what I would derive from this story.

To become like Resh Lakish and be able to come up with these objections, one would first need to memorize and review Tannaitic literature (or whatever the source material would be in your Torah topic of choice), develop a comfort and mastery over it, and be able to call up that material in order to challenge any newly introduced idea.

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