Thanks for posting the "question." I haven't heard of that question asked before,...actually for me, I uncovered, and thus dissolved the answer before the question while unfolding an understanding of Who's Who in Duality.
I suspect that most people (those interested in a less dense/crystallized form of consciousness) come upon the observation of something between "the me inside, and the world [that this perceived inside perceives] out there." Neither the inside, nor the outside can ever answer the question of what the "When" is, because both the perceived inside and outside is attached to the past, and thus cannot be part of the solution, or the answers dissolution.
No intellectual, emotional, sensory or instinctual perception can see the present,...they can only appear to interact with the past,...with what is not real. We not understand When, the concept of non-separation vanishes, because such a concept merely pointed to what ego is not.
There is no non-separation because separation doesn't exist. Ego likes to speak of non-separation to avoid the present,...the present is "When" the real Self is. There is no perceived separate self without ego. The is no tolerance of fallacy without ego. There is no encouragement towards others regarding their beliefs without ego.
Mahamudra suggests that before authentic experience can occur, one must let go of fear and hope. Unfortunately, many believe that they have direct experiences,...in truth, they do not. Any experience that arises through the veils of belief, can only be experienced through the condition of that belief,..and thus, it is not an authentic experience,...it is merely a dream of experience.
People on the Long Path do not have significant experiences,...only distracting dreams.
JV Marco