Do you just want a casual companion, or are you seeking commitment and marriage? Ask him what he believes, how it informs his life and whether he would be willing to marry or commit to a non-Jew.
If you're having fun with your man and don't want a lifelong commitment, you might not need to get deeper into his beliefs. Ask how he expects his family and community to respond to you.
Interfaith dating always presents challenges, and Judaism is a notoriously close-knit religion that traditionally forbids interfaith marriages.
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Don't obsess over his practices; you need to know whether you two connect as a couple before you delve deeper into his faith.
Consider what you're looking for in the relationship.
These are all standard questions children ask to determine how they fit into their world.
Why does my family celebrate some holidays and not others?
Communicating effectively and being aware of cultural differences will increase your chances of building a successful relationship with a Jewish man.