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Mommania, from what you have written, it seems to me that getting him interested in a Birthright trip may be the best thing to do. However, there is an age limit – I think the cutoff age is 26, but I may be wrong. Although the trip itself is not very long, many young people elect to stay on in Israel for at least another month. Of course those that stay have generally travelled with at least one friend. I don’t know if the Birthright/Taglit office will assist in matching you with a room mate for an extended visit. If he has been seeing this young lady for quite some time, a trip of just a couple of weeks would probably not break up the relationship. Do you know if his family has any plans to talk to him about this situation or to ask him if the girl involved might be prone to converting to Judaism? It is a difficult situation and I commend you for taking an interest.