As much as I'd like to champion the idea that emotions are something that should just pour out as they are relevant, there is a sense of culturally built up shame over being allowed to do it. As a kid I found it a lot easier to cry, but after a speech about how 'guys don't do that' from my father I pretty much lost the ability to for a long time until later, the feelings that'd have elicited it still there but otherwise having to find other ways of expressing themselves.
With the attempt to avoid negative feelings I found a general sense of emotional deadening following, or more accurately a disconnection from the display and recognition of my own feelings to the point of others seeing a flatter affect than what was real which only further fooled myself. With it happiness also became harder to seek, leading to no real room to feel much at all other than moments that'd catch me off guard, leading to an appreciation for art over how it could capture feelings from within controlled conditions.
That being said, I still can't really cry even when the body is really primed to unless something is jarring enough to help push me over that line. There's such a sense of internalized shame with the concept of it that otherwise is very difficult to drop, even with rhetoric and reasoning as to why it's better to be expressive. I'd ideally say your answer:
Um. When you feel like it ?
Sadly though it's rarely that easy even for fairly functional people over a multitude of details, be it cultural values, not wanting to face feeling like a victim, the shame of it drawing attention to you, etc.
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