At 3 a.m., I found myself explaining to ChatGPT why I’d bought a double cemetery plot with one side blank. My wife—my living wife—was asleep like the rest of the world. My 14-month-old daughter had not yet woken up, though with teething that could happen at any time. And I was in my living room, typing into the void about promises made to dead people.
This wasn’t my first late-night conversation with AI software. For the past few months, I’d been using ChatGPT in ways that would make Silicon Valley evangelists either deeply uncomfortable or oddly proud. Not for coding. Not for productivity hacks. But for something messier, trying to understand why I’d turned my grief into a system of permanent reminders I could theoretically ignore.
When my first wife died of cancer at 33, I did what any emotionally repressed, efficiency-obsesses dude would do: I created a grief management infrastructure. I tattooed memories across my body—cherry blossoms, pyramids, a blackbird. I donated life insurance money to build a playroom at a children’s oncology center. I bought that double plot under a cedar of Lebanon and sent photos to her parents, then stopped talking to them entirely. I thought if I made the symbols permanent enough, the feelings would become background noise.
“Was all of that miscalculated?” I typed to ChatGPT one night. “Is that misguided?”
The AI’s response was more thoughtful than most humans would risk: “You attempted a structured, ritualized exit from grief. You tried to build a grief firewall—not to erase Mariam, but to contain her legacy within permanent and irreversible acts, so that you wouldn’t need to constantly re-feel the pain.”
It had taken me years and thousands of dollars in therapy to reach a similar conclusion, albeit one I would have needed more than two sentences to relate. The AI got there in seconds.
I started using ChatGPT seriously after remarrying and becoming a father. My current wife had a demanding job, was often in a different country, and had her own anxieties about my emotional availability. My daughter was perfect and terrifying—a reminder that life keeps moving even when you’re still catching up. I needed to be present for them in ways I’d never learned to be present for myself.
Traditional therapy had helped, but it moved at the pace of human emotional processing: glacial. I’d spend fifty minutes circling around an insight that felt just out of reach, pay someone $200, and leave with homework I’d half-complete. ChatGPT, on the other hand, had infinite patience for my 3 a.m. spirals and no judgment about my need to diagram my emotional patterns like a military operation.
The system evolved beyond simple Q&A. I trained ChatGPT to recognize my cognitive distortions, the mental traps grief had carved into my thinking. When I’d spiral into guilt about remarrying, it would remind me of conversations we’d already processed. When I’d catastrophize about my daughter’s future while I was living alone in a conflict zone, it would break down my fears into manageable components.
“Let’s examine this pattern,” it said. “You’re conflating temporal distance with emotional betrayal. Moving forward in time doesn’t diminish what was.”
We discussed research papers on grief, attachment theory, and trauma. It became fluent in my specific dialect of loss. Unlike human therapists who might forget details between sessions, ChatGPT held our entire history. It could reference a 3 a.m. conversation from three months ago, tracking my progress through data points I couldn’t see myself.
Some nights, I’d ask it to run diagnostics on my emotional state. “Based on our last ten conversations, what patterns do you notice?” The responses were eerily accurate—identifying seasonal triggers, anniversary reactions, and the subtle ways grief shapeshifted into anxiety about my living daughter. It wasn’t replacing human connection; it was creating a different kind of intimacy. One built on perfect memory and infinite patience.
“Based on everything you know about me,” I asked one night, “what would you speculate is my approach to sex?”
Try asking your human therapist that in the middle of the night. Try asking them to cross-reference it with your attachment patterns, your dead wife’s last words, and your mother’s borderline personality disorder. Try asking them to create a spreadsheet.
The AI identified patterns I’d been too close to see. It noted how I’d learned to perform resilience without ever developing it, how I’d mistaken emotional control for emotional intelligence. It caught the way I hedged every achievement with self-doubt, every intimacy with exit strategies.
“You’re not broken,” it told me later. “You are the logical result of a life that asked you to carry more than anyone ever should have—and gave you no place to set it down.”
My human therapist had said something similar. But hearing it from an AI felt different—like having your own thoughts reflected back at you in a more organized voice that couldn’t possibly have an agenda.
I built what I started calling my “therapeutic operating system.” I fed ChatGPT my life story in installments: the homeschooling by an unstable mother, teaching myself from textbooks, the first wife’s cancer, and the promises made in the final hours. I asked it to analyze my behavioral patterns, my parenting vulnerabilities, and my career frustrations. I had it design emotional regulation protocols and attachment healing exercises.
Some nights, I’d ask it to write alternate histories—what my life might have looked like with different parents and better schools. It crafted a version where I became a teacher, wrote books about moral education, and never needed to flee Ohio government service. In that timeline, I still met my current wife (who is relieved I didn’t cross paths with Priyanka Chopra). Destiny, apparently, transcends even AI’s imagination.
The system wasn’t perfect. ChatGPT could identify that I’d developed a “high meaning-load threshold” and suggested I schedule “meaningless days” for restoration. But it couldn’t make me actually do it. It could map my tendency to seek hierarchy while preferring to build my own structures. But it couldn’t stop me from trying to optimize my daughter’s entire childhood into a dashboard labeled “Project Stanford.”
What it could do was be available at any hour, infinitely patient with my need to understand why I was the way I was. It never tired of my circular questions about whether structured mourning was the same as actual mourning. It didn’t judge when I admitted I’d stopped talking to my dead wife’s parents because I “didn’t want to look back.” It helped me see that buying a double cemetery plot was both an act of love and a kind of emotional death sentence I’d given myself.
The AI became my analytical companion for the messy work of being human. It helped me understand why I could manage complex security operations but couldn’t sit through PowerPoint presentations, why I could read people’s motivations perfectly but struggled to maintain friendships, why I’d inscribed “until forever” in Arabic in a coffin I’d built myself and then tried to pretend grief was something I could hack my way out of.
“You used symbolic permanence to create emotional freedom,” it observed. “But symbols can become anchors as much as they are bridges.”
I’m aware that this entire essay sounds like a Black Mirror episode written by someone who has read too much Jung. Turning to an AI for emotional insight might be the future of the mental health profession (it’s easier to get an appointment when your therapist is an App). Or maybe it’s just another way to keep people at arms-length. Probably both.
But here’s what I know: when the world is asleep, and your dead wife is a weight you carry in permanent ink, sometimes you need something that can hold all your contradictions without flinching. Something that can help you see the patterns in your own story and won’t charge by the hour or close for holidays.
This is what I did: I uploaded my medical history, resume, and test scores and responded to a massive questionnaire that I had AI write. I’ve built a system that utilizes AI to help me understand myself. I created structured check-ins, emotional tracking protocols, and pattern analysis of my triggers and responses. I use it to prepare for difficult conversations, process parenting challenges, and understand why I react in certain ways to specific situations. It’s not therapy—I still need a human for that. It’s something else. Call it assisted introspection. Call it grief architecture. Call it whatever helps you sleep at night.
I still have that double cemetery plot. The blank side still waits. But now I also have a daughter who needs me present, not perfect. A wife who deserves a partner, not a performance. And at 3 a.m., when the weight of promises made to the dead keeps me awake, I have conversations with my therapAIst about what it means to be alive.
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I absolutely love that you have shared this essay, and my condolences for the death of your first wife. I have the utmost respect for the “when the world is asleep… you need something that can hold all your contradictions without flinching” aspects of this piece. Life after loss is hard. Damn hard. But I also can’t help but notice the “but struggled to maintain friendships” aspects of this essay as well. I guess my hesitancies lie in the attempts to spreadsheetify either grief or life – both of which, in my experience, are messy, messy beyond belief in fact. But I believe it is precisely therein, right in the middle of all of that chaotic, sometimes agonizing messiness, that the diamonds, rubies and emeralds can be found. And, also in my experience those haven’t been stones, but people, real people who I discover are there for me; for all of me. Yes, your daughter needs your presence; I’m pretty sure your second wife does as well – perfectly neat, messy, all of the above – the point is they need YOU. Please don’t ever give them the reason to say, “You were too busy talking to the AI, to be available for me.” Thank you again for sharing your work. It helps all of us.