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Basic religious compatibility will often be known before the first date but during the dating you have to get a more specific idea of whether you really are religiously compatible.
These kinds of things can come out naturally during discussions on the first date. On the 2nd and 3rd dates you might want to go into more of an “interrogation mode” but if it can be brought up naturally that might be less awkward. Obviously you both know that this is a shidduch date so it’s not such a big deal by the 2nd or 3rd date to be discussing it outwardly.
In terms of the discussion, it should be exactly that – a discussion and not a yes/no interrogation. Often people will have a question like “do you watch movies” and will immediately passul based on the yes/no answer. If you would discuss why, when, what etc you can get a better idea of what the person really holds and how willing they are to compromise after marriage. If you are already on a 3rd date and like the person, it is worth your time to put the effort into those discussions before breaking up. I’m not saying you should compromise your own religious level but rather that the answer that the other person gave might not be what it seems.