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Question #1 - I continue to struggle with defining my hashkafa and often find that this issue is more prevalent in women, as it may come down to the fact that I don’t have a Rav who I turn to in a shiur setting etc. How does Rav Burg think this can be achieved for someone who strongly feels they are in need of that clarity that a somewhat more defined path could provide.
Question #2 - I think it is easier for boys to know how they identify hashkafically. They have shiurs or rebbes that they may identify with or follow, while girls don’t necessary have something like morning shiur, night Seder etc. Since boys essentially have these different types of learning groups (topics of chassidus, or more litvish, etc) i think it is easier for them to know where they’re holding. For me, I find it extremely difficult to know what type of guy I “need” or to tell a shadchan, because I never really labeled myself as anything. I’m a frum yid! - what else do I say?