Because Jewish dating often begins between two people who may not know each other well there may be some initial difficulty in being able to converse freely and easily.  The conversation between the two is absolutely vital in learning to know the other party, so each one needs to make the effort to talk to each other and to be able to discuss meaningful subjects.

Some people are so challenged by the simple mechanics of Jewish dating which doesn't occur casually that they simply are too nervous to be themselves may be wise to do some role playing with a trusted same sex friend.  If a person is extremely shy or requires additional time to be at ease enough to talk easily, the best date for them may be a patient conversationalist who is experienced in getting other people to enjoy talking about themselves.

Jewish dating is about learning to know the other person, but even a person who is an excellent conversationalist may find that it is difficult to know what subject are safe to discuss and how much personal information should be presented during the beginning stages of dating. A good rule of thumb would be to use the first one or two dates centered on topics which you would be comfortable discussing with the stranger sitting next to you during a long airline flight.  It could be data about you background and about yourself that is neither too personal nor too revealing of any strong emotions which you may have.

Specifically, some of the subjects which would convey information about yourself without sharing closely held personal information might be

• Talk about your hometown and what it was like to grow up there.  Are there unique features about the town itself?  Would you return to live there if you could?  Do you still have family living there?

• Relate what led you to choose your school or yeshiva or profession.  Do you still think you made the right choice, and if so why? If you had it to do over again, would what would you differently?

• What activities do you head for when you have free time?  Do you have a hobby?  What about the hobby appeals to you?

• If each of you has visited a particular city or country, you could share your impressions of the locale.  What did you find most memorable and least memorable about the location

• A good topic of conversation is learning what the other person has read or watched through other media recently.  What was the reaction to the subject and how could it have been handled differently or better?

Because the Jewish dating system is all about learning about the other person, if one is comfortable talking it's all too easy to monopolize the conversation, talking about their own likes and dislikes, while ignoring the fact that each person should be learning more about the other.  A good rule of thumb for enjoyable Jewish dating is to be certain to listen more than you talk.  Ask open ended questions which can not be answered with a head shake or simple yes/no.  Ask the questions which reveal something you genuinely want to know about the other person, not just for the sake of making conversation.