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R' Moshe Feinstein in Even HaEzer 4:60 writes that it is absolutely prohibited, not just as a nice practice, but involves a Torah prohibition. Among other points, one thing he writes is that in his understanding of the Rambam, speaking to a woman in an affectionate manner is included in the Torah prohibition of illicit relationships.


3

In my (limited) experience, this is a fairly common thing. Rabbis often meet many different people in the course of their work, and person A might be a woman who has been looking for a match, while person B might be a man looking for a match. Many derivatives of this exist, such as "person A has brother/sister looking for a match," etc. In this case, ...



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