Don’t ever ask yes/no questions of the other person. A good conversationalist is a good listener who asks open-ended questions of another person. For example, do not ask, “Do you like to eat cholent on Shabbos?” Ask, “What ingredients do you think should absolutely be in a really good cholent?” Or, “Do you like to read?” is not as good a question as, “What types of things do you like to read about?” “Why?” What is your idea of an ideal vacation? You get my drift. The idea is to ask involving, engaging (pun intended) questions that demand a thoughtful and not one-word anwer, so you can dialogue together.
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