Imagine a new בחור in ישיבה sits down next to you during lunch. You ask “What is your name? Where are you from?” Would you then start discussing how you react when you get angry? Of course not. You wouldn’t even bring up less sensitive השקפה topics. However, as time goes on, you get to know each other better. Then you end up discussing more השקפה, and eventually even sensitive topics. A date is the same way. The first date you are just getting to know each other. It is not the time to have deep discussions. Moreover, they are not yet necessary. It’s surprising how much you can learn about a girl when she talks about herself.
Some good topics to discuss on the first date are: family, interests, schools she attended/is attending, hobbies, and her job. Questions like “Did you like that?”, “What do you like or dislike about it?”, “How do you feel about that?”, and “What makes you feel that way?” keep the conversation going and help you understand who she is. You may also want to say a vort on the פרשה during a lull in conversation.
The second date is a continuation of the first one. Use the time in between dates to review the conversations in your mind and prepare follow up questions. Ask for more details and her opinions. Other good topics are parents’ jobs, grandparents, camp, and what she does to relax.
On the third date, you should already be throwing in light השקפה topics (just don’t get personal yet). The gauge to know if you are ready for a topic is if you feel comfortable discussing it. Some good topics are חינוך, the שבת table, and the husband helping in the home verses him learning. It is smart to ask how her parents deal with these issues and then ask if she agrees with their approach. This way the questions are less direct and the answers are more concrete. Other good topics are: different ישיבות and Bais Yaakovs, cellphones, texting, internet, and the public library.
he fourth and fifth date get gradually more personal and deep. Some good topics are: how to react to anger, upset, or anxiety, what it means to be Jewish and why we lead our lives the way we do, and a general plan for life. Many times, it’s easier to discuss ideas as they relate to others. For example, you can say ‘I know a person who did such and such…’ and then ask for and give personal opinions. This way, no one feels put on the spot (obviously, make sure to stay away from לשון הרע). Interspersing light conversations between the heavier ones helps in keeping the atmosphere from becoming too intense.
Additionally, girls are more focused on impressing than boys and may therefore hide their opinions in fear of ‘turning off’ the boy. To avoid this, have her state her opinion first whenever possible.
Another noteworthy point is that the girl should not feel like she is being interviewed. Rather, he should show interest in her sharing her thoughts with him.