The discussion in the most recent chapter about Pure Vanilla Cookie not really understanding Shadow Milk Cookie at all (despite wanting to) is so fascinating to me specifically because Shadow Milk Cookie has given Pure Vanilla Cookie multiple openings to understand him and the things that made him the way he is.
The first time was more subtle in a lot of ways, I suppose, but most of the ways in which Shadow Milk Cookie tormented Pure Vanilla Cookie in chapters seven/eight of Beast Yeast were some form of projection of his own traumas and wounds.
One of the visions Shadow Milk Cookie shows Pure Vanilla Cookie early on in chapter seven is of cookies first despairing, begging for reassurances he cannot give, and then demanding his power and knowledge. "What if there's no way for us all to be happy, what if there is no answer? Tell us where to seek healing! Tell us how to be healthy, live in wealth and happiness! Use your power! Share your power with us! Do it if you truly care!", the cookies in Pure Vanilla Cookie's dreams beg, which..is something we know The Fount of Knowledge suffered a lot of. Even "It's not fair! You don't deserve this power! It's mine!" is an easy parallel to things Shadow Milk Cookie has experienced. Yes, at the end of this sentence he dips into a sentiment aimed at Pure Vanilla Cookie specifically, but the idea that he does not deserve the power he has is, like previous things within this scene, easily paralleled to things Shadow Milk Cookie experiences. After all, we see Shadow Milk Cookie on several occasions tormented by the 'failings' of The Fount of Knowledge, the ways in which he was not seen as 'deserving' of his power; "O Fount of Knowledge, you don't know anything, so why are you The Fount of Knowledge?"
Later in the chapter something very similar happens when Shadow Milk Cookie forces Pure Vanilla Cookie into an impossible situation of needing to comfort a crumbling cookie in their final moments. Pure Vanilla Cookie is forced into a scenario where nothing he could possibly say would make things better, whether he tells the truth or not, there is nothing he can do to fix this, and no matter what, the horrible outcome will be his responsibility. In the end, Deceit is presented as possibly a better option, the kinder option, though even then it is only the lesser of two evils, because this situation is despair all the way down. This, again, directly parallels things we know Shadow Milk Cookie went through, impossible situations in which despair is the only outcome, and yet somehow, Deceit manages to hurt less than Truth. This exact scenario may or may not be something Shadow Milk Cookie has lived, but it is the kind of thing The Fount of Knowledge suffered frequently, for thousands of years, and that perspective is now being shared with Pure Vanilla Cookie.
Now, I absolutely think the conscious goal of these acts were primarily to torment Pure Vanilla Cookie. However, I have also always interpreted much of the torment he inflicts in chapter seven as a gambit to be understood. After all, we see in chapter eight that Shadow Milk Cookie's goal isn't really to get his souljam back. He likes The Truthless Recluse, he likes being around someone he thinks understands him and his fall, someone he thinks has taken that same fall. It's spelled out pretty clearly in the text that a big motivator for Shadow Milk Cookie in this scenario is loneliness. Pure Vanilla Cookie interprets it as the kind of loneliness that can be resolved by holding out his hand and offering friendship, but I think this kind of loneliness that begs to be seen and understood, and that part of what scared Shadow Milk Cookie away from accepting the companionship he clearly desires is that his gambit for understanding was not met with true comprehension.
Of course, we then see a more explicit gambit for understanding from Shadow Milk Cookie in chapter fourteen. Pure Vanilla Cookie says he wants to understand him, practically begs to understand him, and Shadow Milk Cookie responds directly by giving Pure Vanilla Cookie another opening to do so by literally forcing him to walk a mile in Shadow Milk Cookie's shoes. And yes, Shadow Milk Cookie is being very aggressive here, but that doesn't take away from the fact that he, lonely as he is, showed Pure Vanilla Cookie everything he could need to understand him as he was asking to.
Pure Vanilla Cookie is made to directly live through the impossible decisions, the crushing weight or responsibility and blame, the choices where every answer is wrong, every answer leads to despair. A being made to grant knowledge who watches others shatter themselves and others under that knowledge over and over again, just to demand more, and more, and more. The Fount of Knowledge cannot protect anybody, The Fount of Knowledge cannot even protect himself from the boundless cruelty of the world, and Pure Vanilla Cookie is shown the pain and confusion and helplessness of this cycle directly (albeit on a much smaller scale..after all, pure vanilla cookie lives through two decisions as the fount of knowledge, shadow milk cookie had thousands of years to break apart under the weight).
Possibly most interesting is that Shadow Milk Cookie does not just force Pure Vanilla Cookie to live through it, he also talks to Pure Vanilla Cookie, tells him things I think are extremely candid to the darkness of Shadow Milk Cookie's mind; "Do the gods, the witches, not care about us at all?", "I just lied to them..but why does it feel like they're happier this way?", "Why do the gods..the witches..why did they send us such pain?! What do they want from us?!", "Why do stories woven with lies at times hold greater power? Why do they make cookies happy?"
One could argue that Shadow Milk Cookie is a liar, that we can't trust these visions to actually reflect their inner world or pain because he might just be showing Pure Vanilla Cookie whatever he thinks will break him. But I find this argument to be weak, considering we've seen into Shadow Milk Cookie's mind and past several times.
We hear his internal monologue while he's trapped in silence in chapter fifteen, we hear more from him in the prologue to Timeline of Fate, we see how miserable it was to be The Fount of Knowledge in his Dominion of the Beasts segment, in the most recent chapter we get to read these same questions (cookies preferring deceit over truth + the question of the witches) repeated over and over to the point of madness in the writings of The First Headmaster.
It is understandable for Pure Vanilla Cookie not to understand the opportunities he's been given. Shadow Milk Cookie is a very damaged person, and not one who enjoys being honest or vulnerable. When he shows these hurt parts of himself, he does so very aggressively, and in many cases in a way that actively obscures the reality of his suffering behind layers of confusion and chaos. I do not fault Pure Vanilla Cookie for not understanding, I do not even think it's necessarily his job to (though i do think shadow milk cookie, generally, is deserving of help and understanding).
But since Pure Vanilla Cookie so desperately wanted to understand Shadow Milk Cookie, I think it's extremely relevant to the conversation to point out that Shadow Milk Cookie- in his own destructive way (because he is not in a place where he could possibly have a vulnerable clear conversation about these things)- has tried very hard to be understood by Pure Vanilla Cookie, and has watched the person who claims to want to understand him and be his friend repeatedly fail to see him at all in these attempts.
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