What type of person is the one that observes an outsider looking in, that is more outside?

That would be a voyeur, or a private detective.

A private detective investigating a private detective who is observing a voyeur.

@CWOTUS – Good answer! However, even though I didn’t mention it, and I should have, what kind of character or personality does this type of person have?

@rebbel – I like this one even better, Reb, thanks.

@Mantralantis Thank you, thank you, but I could not have done it without being kick started by @CWOTUS!

@rebbel – Yes, yes, of course, you’re right, my good man!

A spy?

Most people do this. In today’s world it’s difficult not to because so much of it (the world) is filtered through one screen or another, via images or video that other voyeurs have recorded for us.

It is exactly like this scene from Don DeLillo’s White Noise, which was published back in 1985. Maybe you’d like it, @Mantralantis.

Murray is commenting on the photographers, who he says ‘are taking pictures of taking pictures’ – but of course Murray is also a sort of voyeur, and the narrator (Jack) is yet further removed as he watches Murray watch people watch the barn, and then the reader is on yet another level, and so on and on, and you can see how it becomes ridiculous and recursive very quickly.

In terms of the ‘type of person’ that your question is asking about: maybe the type of person that does this (watches watchers) is one who pretends to be above the longing we feel for participation, whether it’s participation in a myth or a cultural experience a social movement, or what Murray calls a ‘collective perception’. Or maybe there are other reasons.

@vine – Thanks. That seems very intriguing to me indeed, even if a bit ridiculous. About DeLillo’s White Noise I mean. And I might just check it out someday.

either or both: “god”...“damn lonely”