Adventing
Why AI Cannot Teach and How It Might Occasion Learning
There are two things nearly everyone selling AI in education promises it can do.
The first promise is that it should be able to deliver instruction directly. The prevailing hope is that AI can (or will soon be able to) explain a concept, answer a question, and provide information clearly and patiently. The basic idea is that AI becomes the tireless teacher; it never suffers from the exhaustion that eventually overtakes even the best human teacher.
The second promise is that it could serve as a Socratic tutor. Here AI is asking questions rather than handing over answers. Again, the aim is similar though: the goal is to draw understanding out of the student through dialogue, replicating the method of the philosopher who claimed to know nothing while somehow producing some of the most significant thinkers in Western history.
To this point (and I stand by it) AI can’t really deliver on either of these promises. Both direct teaching and Socratic questioning are key principles of education that AI is able to contribute to in interesting and novel ways, even if our current AI systems hardly live up to the hype of what they are supposed to do in this regard.
So in this essay I want to take a different tack. Let’s assume both promises are real and attainable. AI does elements of both with increasing fluency. Let’s give the bro-archy and ed tech the benefit of the doubt and assume they can build AI systems that provide on-demand Socratic questioning and supremely reliable content delivery.
Does fulfilling these two promises really deliver on the work of education itself? To me, at least, this is the more interesting question because those are pedagogical approaches that optimize for exactly the wrong thing: closure.
The Problem with Closure
In my early theological writing I developed a concept I called adventing, drawing on the liturgical season of Advent: the weeks of waiting and anticipation that precede Christmas in the Christian calendar. Advent is a space of possibility. It is characterized by longing and waiting. It is fundamentally a time defined by its incompleteness: by something hoped for but not yet arrived. And, it functions as Advent only so long as it stays open. The moment what is awaited arrives, something essential is lost. (You always knew Christmas ruined something...it just happens to be that what it ruins is the possibility of Advent).
Now, I should say more clearly, none of this is meant to indicate that arrival is bad. (Yes, Christmas is off the hook, again). But, because the quality of existence that belongs to the not-yet cannot survive its own fulfillment, adventing only works insofar as what it hopes for doesn’t completely fulfill that hope.
This is not a uniquely theological insight. Søren Kierkegaard understood this and claimed something similar when he said that certain truths cannot be directly communicated. They can only be occasioned.
Consider Either/Or, which Kierkegaard published in 1843 under the pseudonym Victor Eremita, the “victorious hermit” who claims merely to have found the manuscripts hidden in the drawer of a secondhand desk. The book sets two ways of living side by side and refuses to choose between them. The first belongs to an unnamed aesthete devoted to pleasure, novelty, and possibility; the second to a judge who defends marriage, duty, and the decision to bind oneself to a single life. Kierkegaard offers no verdict. The title is the whole argument: either, or. A reader who is handed the correct answer has not actually chosen, and for Kierkegaard the choosing is the entire point. The ethical life cannot be received as a doctrine. It has to be willed by the person living it.
This is what Kierkegaard meant by indirect communication, and he practiced it with extraordinary deliberateness, writing under a crowd of pseudonyms, constructing elaborate situations, manufacturing productive confusion instead of delivering clarity. The reader who receives a truth directly has only received information. Truth, in the sense that matters, has to be arrived at. It has to be undergone.
Plato understood this too, and he built it into the very form of his writing. The Symposium never speaks in Plato’s own voice. It reaches us secondhand, narrated years after the fact by Apollodorus, who had the story from Aristodemus, who was actually there: a chain of report that keeps the author offstage much as Kierkegaard’s pseudonyms kept him offstage in his own books. The occasion is a drinking party at the playwright Agathon’s house, where each guest takes a turn praising Eros.
When Socrates’ turn comes, he does not offer a theory of his own. He relays what he was once taught by Diotima, a priestess of Mantinea, and what she taught him was a myth. Eros, she said, was conceived at the feast for Aphrodite’s birth, the child of Poros (Resource) and Penia (Poverty). He inherits his mother’s need and his father’s cunning, and so he is forever poor, forever scheming after the beautiful things he lacks, never in secure possession of any of them. Desire, on this account, is a condition of being in between, of not-having, woven into the structure of the soul rather than a hunger that good fortune eventually fills.
What Diotima offers Socrates is not a definition of beauty but a staircase. She describes an ascent that begins with the love of a single beautiful body and climbs, rung by rung, to all beautiful bodies, then to the beauty of souls, then of laws and ways of life, then of knowledge, until at the summit something comes into view that can only be glimpsed and never grasped: Beauty itself, which does not come and go and cannot be owned. The dialogue does not hand the reader that vision. It stages the climb and leaves the reader to attempt it. Eros, genuine desire, is not satisfied by its object. It is constituted by longing. Fulfill it completely and you have not satisfied desire. You have ended it.
Education at its deepest level works the same way. It is a type of desire that cannot be directly communicated. The student who has truly been educated is not the one who got the answer but the one who has been given a longing, a capacity for wonder that expands as it meets more of the world. Adventing is the discipline of protecting that longing and wondering. You cannot hand someone a transformation. You can only build the conditions under which transformation becomes possible.
Or if you want to be a little more colloquial, “You can lead a horse to water, but you can’t make it drink.”
Why Direct Instruction Falls Short
Let’s start with direct instruction: AI explaining, answering, clarifying. It does not fail because it is inaccurate or unhelpful. (If anything, clear explanation is the one thing the current systems are genuinely good at.) It falls short because it delivers closure.
When a student asks a question and receives a clear, complete, well-organized answer, something happens that feels like learning but is not quite learning. The question gets resolved, and the discomfort of not-knowing is relieved. The result is nearly always that the space of possibility the question had opened is closed.
This is not always a loss. Some things worth knowing do not require transformation to know them. Facts, procedures, definitions: these can be delivered and received without significant cost. Direct instruction serves perfectly well here, and AI serves direct instruction very well indeed. (This is the part of the sales pitch that happens to be true.) The trouble begins only when we treat that transaction as the whole of teaching.
Because education, in the fullest sense, is the formation of a person. We could name this in all kinds of ways. It is the development of capacities; it is the cultivation of judgment; it is the awakening of what the thirteenth-century theologian Bonaventure called wonder. If you have been wondering about my use of wonder, I’m using this word intentionally. And, in deference to my former colleague Tyler Atkinson, please get it straight that wonder is not curiosity.
Curiosity wants to close. It wants to find out, to know, to resolve the question that opened it, and it is satisfied the moment the answer arrives. Wonder behaves differently. Wonder is content to remain open, to marvel, to be undone by what it encounters, to find itself enlarged rather than relieved by what it discovers. Curiosity drives toward the answer. Wonder is enlarged by the question.
Direct instruction, however sophisticated, produces curiosity at its best. It cannot occasion wonder, because it is built to answer, and answering, when it comes too quickly and too completely, forecloses the advent before the student has had time to live inside it.
Why Socratic Tutoring Fails
Now the Socratic tutor is the more interesting case, and the harder one to argue against, because it looks like it is already doing what I am asking for. It asks rather than answers. It follows the student’s thinking instead of leading it (or at least it is supposed to). On the surface, it holds the space open. (This is the version the demos love, and I understand why.)
But here is the catch. A convincing imitation can reproduce the form of a thing while missing the core that made the thing what it was, and the Socratic bot is a facsimile of Socrates in exactly that way. What made Socrates Socrates was not his method. (The method is the part you can copy, and it turns out to be the least important part.) It was his genuine openness to being transformed by the encounter. He was not performing ignorance. He was vulnerably present to the possibility that the person in front of him might occasion something in him he had not anticipated.
To harken back to some of my more recent writing about What AI Cannot Do, Socrates has something at stake that AI can never have. He had duration: a life of formation, of previous encounters that had shaped him, of commitments and questions he carried into every conversation and that every conversation acted back upon.
When Socrates questioned someone, he was not running a pedagogical procedure toward a destination he had already chosen. But, this is the best a Socratic tutoring bot can do. Instead, Socrates genuinely did not know where the exchange he was having would end. He opened himself to being occasioned, to having the conversation change him as much as it changed his interlocutor. This is why the dialogues so often end in aporia, in unresolved openness. Socrates did not withhold the answer. He did not have it, he wanted it, and the finding was always incomplete.
An AI Socratic tutor always has an end. Beneath the questions, it is always moving toward something: a correct understanding, a learning objective, a destination dressed up as discovery. It cannot be genuinely surprised. It cannot be changed by the encounter. It has nothing at stake, no duration, no self that hangs in the balance of the conversation.
In essence, AI can only perform openness while being built for closure.
Students feel this, even when they cannot name it. You can feel it yourself the next time a chatbot asks you a warm, curious follow-up: the warmth is real enough, but the curiosity is set dressing. The questions feel like a road already mapped. The dialogue feels like it is leading somewhere the bot already knows, because it is, and it does.
What Adventing Actually Looked Like
For several years I taught a course in political theology. It was not my area of specialization, which may be part of why it worked. (Teaching just outside your competence is frightening in precisely the productive way.) I came to the material with my own questions still live, tracing why theological commitments kept surfacing in civic life: why the language of ultimate concern kept showing up in arguments about zoning, schools, and water. We did not stay in the seminar room. We engaged directly with local and state politics, following live questions into places where I could not predict what we would find, and neither could the students.
The course drew, strangely, more students from outside religious studies than from inside it. An advanced theology class would fill with people who had no particular investment in theology and every investment in the questions it was asking. (Nothing reorders a theologian’s ego quite like a roomful of students who came for the politics and stayed for the ultimate concern.) And yet, this is what fit the shape of the work we were doing. The adventing was built into the course from the ground up, because the questions were genuinely unresolved for everyone in the room, including me.
What students carried out of that course was not a conviction that they could change what was happening around them. It was a determination to be heard. There was a recognition that participating in the conversation, to refuse the posture of the spectator, was in itself a good they could choose. They left with something closer to hope than what might traditionally be measured as a learning outcome: a sense of wonder for the possibilities of resistance and action that their more closed educational experiences had quietly trained out of them. Nobody handed them that. It arrived, when it arrived. And, for some that occasioning never came. But for everyone in the space, the course refused to close.
In my own teaching more broadly, the moments that mattered most were never the moments of clarity. They were the moments of productive irresolution: assessments that graded process rather than artifact, conversations I deliberately declined to wrap up, situations where I held back the answer I expected and waited to see what the student would produce instead.
What happened in those moments was something Bonaventure would have recognized as wonder: not curiosity satisfied but marvel deepened. The student became, in those moments, more genuinely other to me. Not more known, but stranger, more genuinely themselves, in ways I had not predicted and could not have produced. The student who recapitulates the expected answer confirms what I already knew. The student who restructures the problem in a way I had not imagined makes the world briefly larger, and in that enlargement something passed between us I can only call mutual formation. They were teaching me. No facts were exchanged. Something harder to name occurred.
Maurice Merleau-Ponty described the deepest form of learning as a kind of incorporation: understanding that does not stay at the level of concept but becomes flesh, that changes how a person moves through the world. The students in that theology course did not leave with a better concept of civic life. They left moving through civic life differently. That is education that transforms rather than informs, and it happens through occasions. Or to put it more formally, it happens through the sustained, disciplined refusal of closure and adventing.
What AI Can Actually Do
This is not the part where I tell you AI has no place in education. Its place is just more specific and more modest than its advocates claim, and more interesting than its critics allow.
If the goal is to occasion learning rather than deliver it, to hold the advent open rather than close it, then AI’s role has to be indirect by design. It is not the teacher. It is not even the Socratic interlocutor. It is closer to a set of conditions for an encounter that still has to happen between a human being and the thing they are trying to understand.
In the bot essays that will follow this piece over the next few weeks, I am trying to develop three tools built on this principle, each designed to occasion one of the three modalities of genuine learning: depth, novel capacity, and incorporation. None of them answers questions directly. None of them performs Socratic dialogue. Each works indirectly, creating pressure and space instead of delivering content, holding the advent open rather than rushing it toward its close.
They will never wonder. But built with enough care, they might hold the space in which a student begins to. Just let the advent stay open a little longer. What finally arrives in it was never ours to deliver, and that is the whole point.