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I'm new to philosophy and as of now, I don't have any knowledge related to what he said in order to properly redirect him to a source that mentions something similar. His philosophy goes like this: If you lose something that you truly didn't care about, you didn't lose anything, but mentioning the fact that you lost it implies that you actually DO care about what was lost. If in fact this is a loop that doesn't have any arguments against it, what is it called and are there any works that have similar core logic such as this one? It's open to any interpretations.

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  • It is strange how something can seem plausible (I've lost something important) but in fact not be the case (I had nothing important to lose). But anyway, apathy and feelings of helplessness are associated with loss.
    – user62946
    Commented Oct 10, 2022 at 6:04
  • You can lose something you don't care about, but perhaps unknowingly need. EG: You might lose a boss who aggravated you, but who had a lot of wisdom to impart that you will now no longer benefit from. Commented Oct 10, 2022 at 13:51
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    Sometimes though, a thing is not truly appreciated until it is lost.
    – user59124
    Commented Oct 10, 2022 at 15:39
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    "Freedom's just another word for: nothing left to lose" - "You don't know what you've got 'til it's gone"
    – Scott Rowe
    Commented Oct 10, 2022 at 16:45
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    Heraclitus famously said something very deep while seemingly illogical like "being exists and exists not", thus once you name the being you lost, the said thing spontaneously exists at least in your conventional Husserlian homeworld as two faces of a coin which means you do care about since per phenomenology any mentioned being-in-itself was necessarily intentioned about by its lifeworld's possible (intersubjective) mind(s)... Commented Oct 10, 2022 at 18:39

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It makes me think of involuntary mental imagery, like where you say 'Don't think of an orange penguin' as a challenge.

Or 'The Game', a mind_game where if you think about the game, you lose the game.

You can give a simple counterexample: Ask if there anything he doesn't care about. If by his own criteria he admits there can be nothing in the category, he hasn't performed a clarification, he's performed a redefinition.

People do this when they say 'Reality is an illusion', of 'The self isn't real'. These statements sound what Dennet calls deepity, but when you look closer they just redefine 'real', and 'self'.

Your friend's quip just redefines 'care'.

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  • I think the 'deepity' statements are like little thought grenades intended to blow up people's stuck thinking.
    – Scott Rowe
    Commented Oct 10, 2022 at 16:49
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Your friend’s philosophy is about loss, and it’s really a profound question because life is really all about big and small losses.

Seneca said we cannot deceive loss, we can only conquer it. He suggested to his mother to study the liberal arts to take her mind off of loss.

The loop you speak of is grief. We grieve the loss of mere things too. Even small things. Time heals all, but it does leave scars.

Happiness is beneficial to the body, but it is grief that develops the powers of the mind. -- Marcel Proust (1871-1922)

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Think, by analogy, of ending a relationship without telling the other person it's over ("ghosting", or an extreme version of it).

You can lose something you didn't want, but it's probably a process (with or without deception)

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  • It's over... I will un-ghost myself from my imaginary stalker gf hahah. Peace / good luck
    – user62946
    Commented Oct 10, 2022 at 14:15
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Since I don’t know anything about the arguments or works you mentioned, I shall try to answer your main question only.

In normal case ‘you’ means the body even though actually it is not. If ‘I’, ‘you’ etc., represent the body, we lose something. Otherwise, (or truly) we do not gain or lose anything ultimately even if we cared about or not.

If the possessor and the possessions vanish at the same time (or the possessor … a moment before), do we say that the possessor lost his possessions?

Usually when people lose their eye sight they say that they lost their eye sight. When people lose their memory they say that they lost their memory. That means even though we do not feel we have something, people feel loss when they lose essential parts like these.

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It may be helpful to draw a distinction between emotional and material loss.

It is possible for a material object to no longer be accessible (loss of an object), and not have emotional attachment to that thing. The lack of that object is an experience of loss, regardless of any emotional reaction to that experience.

If I go to get a pencil and that pencil is not there but another one is, I have lost that first pencil but have no sense of disappointment since the need is fulfilled by the other pencil.

But generally speaking when someone uses the word loss it is used in an emotional context. Loss of a friend or family member, for example. There is an implied emotional connection in the relationships in that context. Therefore we have a necessary emotional reaction to that lose.

Unless I am incorrect it seems possible to me that we can lose something (material loss) while not experiencing emotional loss.

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