Another strategy: Don’t tell him that you are trying to get him to break up with the girlfriend. Do tell him that you need his help to help you with a project and that you are willing to pay him for it. The project is of course going to take place at some kiruv place where there will be an understanding Rabbi waiting nearby to just by happenstance speak with him in general about various things. Once he’s buddies with the Rabbi then your problem is basically over. I would suggest being in touch with someone like Rabbi Wallerstein to arrange this. He has loads of experience in this area and if he can’t help then he’ll lead you to someone who can.
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