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Some strategic questions to try and determine her stance on guns wouldn't be out of line. Or maybe a carefully chosen movie that could help spark that conversation. I'm just thinking that we all try to be careful with our personal information these days and I consider my CHL to be personal information.

I don't know. I think I might not want this woman to know I have a CHL. If I thought I knew her well enough I might let her know I own a gun, but I'm not sure I would let her in on the CHL until we were married or at least engaged. I don't want to be a pessimist, but what if this woman is not the ONE? Then you have an EX that knows you have a gun and a CHL.