“They then mix him the second cup. And here the son asks his father, and if the son has not enough understanding, his father instructs him, ‘Why is this night different from other nights? For on other nights we eat leavened and unleavened bread, but this night all is unleavened…” (Mishna Pesahim 10:4). This would appear to be the source of the custom of having our children ask the Four Questions.

While clearly we must recall the Exodus, why must we ask questions? In truth, if you carefully examine the mishnaic text, you may conclude that there is no such obligation. The words “ma nishtana ha-layla ha-zeh” are generally translated “Why is this night different”, but a better translation might be “How different this night is”. This is the way this grammatical form is understood in such verses as “How fair are your tents, O Jacob” (Num. 24:5) and “How sweet is your love, my sister, my bride!” (Song of Songs 4:10). In other words, the words “ma nishtana” may not be the first words of the child’s questions, but rather the first words of the father’s response.

We find no unequivocal requirement of asking questions in other early sources. For example, the Mekhilta says: “And Moses said to the people, ‘Remember this day’ (Exodus 13:3): From the statement ‘And when, in time to come, your son asks you’ (Exodus 13:14) we can derive that if he asks, you tell him, and if he does not, you do not tell him. Therefore it says ‘And you shall explain to your son’ (Exodus 13:8), even if he does not ask you. But this is only if he has a son, but what is the source for himself alone or between himself and others? Therefore it says ‘Remember this day, on which you went free from Egypt’ (Mekhilta deRabi Shimon b. Yohai 13:3). Here we see how the midrash provides a step-by-step exegesis to show that telling the story of the Exodus is not merely a parent’s educational obligation that is required in the case a child asks, but rather it is a general obligation that applies to all.

But the Gemara does not stop at requiring that we tell the story: “Our Rabbis taught: If his son is intelligent he asks him, while if he is not intelligent, his wife asks him, but if he has not, he asks himself. And even two scholars who know the laws of Passover ask one another” (Pesahim 116a). It is not enough to recount the story. One must ask the questions.

Accordingly, Maimonides rules: “And one must do something different on this night so that the children will see and question and ask ‘why is this night different from all other nights’… if he has no son his wife asks him, if he has no wife they ask one another ‘why is this night different from all other nights’ even if they are all scholars, if he is alone he asks himself ‘why is this night different from all other nights’” (Laws concerning hametz and matza 7:3).
In his commentary to the Haggadah, Dr. Joshua Kulp suggests an historical explanation for the development of the custom:

The notion that a question should open the seder, brought up originally in the Mishnah and that becomes dominant in later ritual, is either midrashic in origin or a reflection of the Greco-Roman custom of beginning the symposium’s discussion with a question. In my opinion, it it likely a combination of both, the idea of starting with a question coming from Greco-Roman custom and the ascription of the question to a child reflecting the Torah. In three places the Torah cited a future question that will be asked by a child to his father and answered in connection to the Exodus. For instance in Deuteronomy 6:20-21, “When, in time to come, your son asks you, ‘What mean the decrees, laws and rules the the Lord our God has commanded you? You shall say to your son, ‘We were slaves to Pharaoh in Egypt…” Similar questions are found in Exodus 12:26, 13:14. Exodus 13:16 lacks the question from the son to the father but does contain an enjoinment for the father to explain to the son…” (The Schechter Haggadah: Art History and Commentary).

Various scholars have attempted to identify the source of the custom and explain its development, but as Kulp observes: “The popularity of this custom is attestation to its ‘catchiness’ – there was no need for it to be anchored in a properly understood textual tradition.”

1. Many halakhic requirements and many customs well-grounded in tradition have not enjoyed the popularity of the custom of having the children ask the Four Questions at the seder. Why has this custom remained so prevalent?

2. Why do we place such emphasis upon the questions? Perhaps an answer may be found in something R. Joseph B. Soloveitchik wrote about questions: “Knowledge in general and self-knowledge in particular are gained not only from discovering logical answers but also from formulating logical, even though unanswerable, questions. The human logos is as concerned with honest inquiry into insoluble antinomy which leads to intellectual despair and humility as it is with an unprejudiced true solution of a complex problem arousing joy and enhancing one’s intellectual determination and boldness” (The Lonely Man of Faith).

3. Answers change in accordance with the questioner. The answers provided to a “wise son” are necessarily different from the answers given to a “simple” son, even if the questions are identical. Would it be correct to conclude that questions can remain pertinent even after the answers are later refuted or become irrelevant? How can asking the questions contribute to keeping the seder relevant? What is the importance of preserving the fixed formula of the questions?