First of all, there is a very important principle taught by the Gaon Rabbi Gershon Edelstein ZTL (brought in Gilyon Mimeged 144): the necessary inquiries about a prospective match should be made before the dates begin (which, in your case, has already been done). The date itself should not feel like a job interview, but rather an opportunity to see whether there is a sense of compatibility, comfort, and good chemistry between the two of you. Therefore, during the dates, it is best to talk about simple, natural, everyday topics.
One thing that is important to try to understand through the conversation, however, is the other person’s hashkafah (worldview), in order to determine whether you are compatible in that area, as cited in the name of the Gaon Harav Shach ZTL (Kovets Mevakshei Torah, vol. 24).
If you find it helpful, here are a few ideas for conversation topics (there is no need to ask about everything—only what comes up naturally and feels appropriate):
- Show interest in her family: her parents, siblings, uncles, aunts, etc.
- Ask about her education and what that experience was like.
- Talk about the family’s rabbi, whose halachic rulings they generally follow, who they turn to for guidance, and what their synagogue is like. Naturally, you can also share about yourself—such as your Mekor Haim, chavrutot, and similar aspects of your life.
- Ask what qualities she admires most in a person.
- Talk about work, future studies, and personal goals: what she enjoys doing most and what gives her a sense of fulfillment. As Rav Edelstein ZTL advised, the focus should be on what brings her genuine satisfaction.
- Ask how she likes to spend her free time: hobbies, sports, volunteering, cooking, or other interests.
- Talk about travel, especially to Israel: which place impressed her the most and why.
- Ask about some of her favorite childhood memories.
It is also worthwhile to sit down with a pen and paper beforehand and think of other topics that genuinely interest you. In general, the questions that come naturally from your own curiosity tend to make for the most pleasant and authentic conversations.
Overall, the best way to show genuine interest is not by asking a long list of questions, but by listening attentively, asking thoughtful follow-up questions (“What was that like?”, “What happened next?”, “How did you feel about that?”), and also sharing some of your own experiences. That way, the conversation flows naturally and becomes enjoyable and meaningful for both of you.
Behatzlachah!
