I was never discouraged from crying. There just came a point that I didn't any more.
I'm not withholding anything by not having cried* in almost exactly 20 years (I do remember the last time I did), I have just never had any urge to do so and wouldn't stop myself if I did. When my great-grandmother died it was emotionally very difficult for me but I never had any urge to cry that had to be withheld. And same for many other personally sad moments as well as tearjerker movies.
What I hate is that is that for many people you apparently aren't actually sad unless you are crying.
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