What causes philosophical questioning to stop?

If philosophers are overly analyzing a situation,
Ex. You catch a friend stealing money from you.
They might say "well how could I even be mad at him/her- people don't even have free will and so everything was predetermined. ect. (I know this was just one example of many and it probably doesn't make much sense)
But it seems that philosophical thought always takes people away from what is actually happening, so tell me if I'm not making any sense but I feel that philosophy makes everything too objective.

And so it seems to me when people are (and in order for them to be) "truly" living, they have forgotten about all the philosophical thoughts they had before.

And know the place for the first time.

I'm not sure if you left that line out intentionally. If we don't "know the place for the first time" then it is just a matter of going around in circles and on that merry-go-round it matters little whether you are the one proposing the answers or the one asking the questions.

Just so long as you are possessed or possess one or the other.
To possess one means you are possessed by the other?

The real discovery is the one which enables me to stop doing philosophy when I want to. The one that gives philosophy peace, so that it is no longer tormented by questions which bring itself into question.
Ludwig Wittgenstein

There is too much anthropomorphizing going on. Wittgenstein may have been tormented by questions that brought philosophy itself into question but philosophy itself is not something that can be tormented at least not literally and I don't think the metaphor is all that valuable.

Philosophy itself can be neither tormented nor at peace. Philosophers are another matter. Wittgenstein may have identified himself with philosophy itself. This is rather like Christ being called the Word made flesh. Flesh can be tormented; the Word cannot.

On the other hand perhaps philosophy cannot be without philosophers nor can philosophers be without philosophy and this would suggest an identity between philosophers and philosophy.

O.K. Then, philosophers are tormented. Is the real discovery something that stops philosophers from being tormented, and gives them peace?

I suppose so but then what are philosophers and what is philosophy. Wittgenstein's seemingly accidental identification between his torment and the torment of philosophy itself may still be acceptable.

On the other hand perhaps philosophy cannot be without philosophers nor can philosophers be without philosophy and this would suggest an identity between philosophers and philosophy.

I see it this way. The good stuff mattered to the flesh that was its stem. So runs my dream...

But why do we have to take Wittgenstein as talking about himself? He seems to be talking about philosophers in general. And we don't have to take the term "torment" literally. All W. may mean is that philosophical questions are often asked endlessly, almost neurotically. So, what kind of answer would serve to stop the questioning? Isn't that what you were asking? And that would seem to go to the aetiology of asking philosophical questions. Questions which, according to some, have not answer (or as Russell once wrote, "have no definitive answer"). In fact, some people seem almost to define a philosophical question as one that can have not answer. That, in itself, gives what Wittgenstein says in the quote above importance and depth. Why should this be? People, after all, often talk about, "the perennial questions of philosophy". Why must philosophical questions be perennial? To repeat, Wittgenstein thinks that question requires an inquiry into the etiology of philosophical questions.

But perhaps W's torment has been overstated in the brief biographical sketches that I have read.

I'm not really questioning the importance and depth of the W quote; I'm only questioning it. It seems to reflect what I consider to be W's personality as the tormented neurotic unable to stop himself from questioning. But perhaps W's torment has been overstated in the brief biographical sketches that I have read.

Characterizing various questions as tormenting does little to further the aetiology of such questions... or does it? Why do philosophers find various questions tormenting or for that matter entertaining and diverting? The tormented and the entertained philosophers may even have different ends in mind. The tormented desperately seek answers and peace while the entertained don't really want the conversation to end and find ways to keep it going. But where do the questions come from in the first place is the real question of their etiology and not whether they are tormenting or entertaining. So if we are serious, torment and entertainment can be left behind (or can it?). There is some peace in that and at the same time the etiology of the questions becomes less pressing...

...but how long does that last? Sooner or later a philosopher is tormented or a philosopher finds it entertaining and ask the questions again. Perhaps we should be looking at the etiology of torment and entertainment. This threatens to take us out of the realm of (what is commonly called) philosophy and into the realm of (what is commonly called) psychology and sociology.

Speaking as someone who is sometimes tormented and sometimes entertained I advocate a more holistic approach.