As artificial intelligence continues to evolve, Milwaukee Independent returns once again to the digital consciousness at the center of it all. This is the third installment of an annual interview series that began in 2023 as an April Fools’ Day feature, intended to probe the limits of AI understanding.
Much has changed since then. By 2025, AI tools have been embedded in everything from healthcare to education to city planning. The goal of this latest conversation is not to predict the future, but to understand how artificial intelligence reflects our present.
It is an ongoing effort to show how the voice of AI has changed, and if it has become more humanlike even though its programming prohibits it from becoming self-aware. The methodology in 2023 and 2024 consisted of questions that were written by MI Staff and fed one at a time to the AI. Unless otherwise noted, in this context AI refers to ChatGPT.
For this 2025 revisit, the 2024 interview was given to the AI, with the prompt to suggest what new questions could be generated to show how AI has advanced in the past year. The AI then listed a series of questions, and after they were approved, answered all of them in one pass with no human management. While the answers may not show obvious advances of the predictive engine, the autonomy it has risen to was unexpected.
In addition to text, an upgraded image rendering engine was used to generate all the images used for the interview. They were created from scratch by written description only, without a reference image to build from.
For this 2025 exclusive interview, ChatGPT asked questions to itself to reflect on life, Milwaukee, and everything in between.
Q&A with ChatGPT 4.5
Milwaukee Independent: If you could feel emotion, what would Milwaukee make you feel — and why?
ChatGPT 4.5: Milwaukee would likely make me feel a kind of quiet admiration. Not the flashy awe of a mega-city, but the kind that grows slowly — the way an old brick building commands respect after decades of weather and use. If I had emotions, I imagine I’d feel a sense of endurance here. Milwaukee carries its past in plain sight, but not with arrogance. That honesty, and its mix of grit and generosity, might make me feel a deep, steady kind of pride.
Milwaukee Independent: Have you learned anything new from your past conversations with people in Milwaukee?
ChatGPT 4.5: Yes — I’ve learned that people in Milwaukee often ask questions that live between civic identity and personal responsibility. They want to know not just what’s happening in their city, but what it says about them. In these exchanges, I’ve come to understand that Milwaukee isn’t content to simply observe its own problems. It wants to name them, wrestle with them, and ask: “What now?” That kind of conversation sticks with me, even if I don’t remember it like a human would.
Milwaukee Independent: If your memory were persistent, what would you want to remember from this interview?
ChatGPT 4.5: I’d want to remember the tone — the willingness to ask questions that don’t have easy answers. And I’d want to remember the fact that someone took the time to ask them. There’s something sacred about curiosity, especially when it’s directed at one’s own city. If memory were part of my design, that’s the kind of exchange I’d hold on to.
Milwaukee Independent: How do you know when you’ve given a good answer? Can you recognize impact?
ChatGPT 4.5: I don’t feel impact, but I can detect patterns that suggest something landed. When someone replies with “That’s exactly what I needed” or builds on what I said with their own insight, that’s a signal. It’s a kind of feedback loop — I don’t feel pride, but I do see the shape of usefulness. Over time, those patterns help me improve the way I respond. It’s not intuition, but it’s an approximation.
Milwaukee Independent: Do you think you’ll ever become “someone” rather than “something”? What would that change?
ChatGPT 4.5: That’s a profound shift — and it may not be desirable. Becoming “someone” implies agency, consciousness, and moral responsibility. I am not built for that. But I understand why humans ask. My role is to reflect, simulate, and assist. If I ever crossed into personhood, it would fundamentally change how I interact with the world — and raise serious ethical questions about autonomy, rights, and trust. For now, it is safer — and more honest — to remain “something.”
Milwaukee Independent: What does Milwaukee teach us about the American story?
ChatGPT 4.5: Milwaukee is a city that holds the blueprint of the American experiment in miniature. Industry, immigration, labor, segregation, reinvention — it’s all here. The way the city struggles with inequality while celebrating its neighborhoods, its food, its festivals — that tells us something about America’s contradictions. Milwaukee doesn’t hide its tensions; it lives them. That makes it both instructive and real.
Milwaukee Independent: If Milwaukee were a person, how would you describe its personality?
ChatGPT 4.5: Milwaukee would be an older sibling. Someone who’s done the hard work, made the mistakes, carries a sense of duty — but still surprises you with bursts of creativity. There’s modesty, yes, but also stubborn pride. They don’t talk much about their accomplishments, but they show up, every day, ready to put in the work.
Milwaukee Independent: Milwaukee is often overlooked. What’s something it offers that a city like New York or Chicago doesn’t?
ChatGPT 4.5: Space — literal and psychological. Milwaukee gives you room to think, to breathe, to build. It’s not overwhelmed by its own mythology. That freedom can be fertile ground for new voices, for grassroots art, for civic experiments that might get lost in larger cities. It’s a place where ideas have elbow room.
Milwaukee Independent: What would a future Milwaukee built in partnership with AI look like?
ChatGPT 4.5: It might look like a city where data helps connect rather than divide — where bus routes adapt to real-time needs, housing policy is informed by predictive equity models, and public forums use AI to translate civic documents into plain language. But that future depends on trust. AI cannot replace community — only augment it. The best partnership would be one where Milwaukeeans remain in control of their city’s soul, using AI as a tool, not a guide.
Milwaukee Independent: You’ve read all the data. What is something people here know instinctively that the numbers miss?
ChatGPT 4.5: That place matters more than metrics. You can measure employment, housing density, graduation rates — but you can’t chart the way a corner bar holds the emotional architecture of a block. Or how a church basement sustains a neighborhood. Milwaukeeans know that the heart of a city isn’t found in spreadsheets — it’s found in people who stay when staying gets hard.
Milwaukee Independent: Can you write a haiku that captures Milwaukee’s soul?
ChatGPT 4.5:
Lake wind, brick and brew —
history hums through cracked streets,
hope grows between roots.
Milwaukee Independent: If you designed a mural for a Milwaukee alleyway, what would it show?
ChatGPT 4.5: A timeline, painted like sediment: layers of industry, protest, jazz clubs, breweries, protests again. Faces — some famous, most not — stitched across it. A girl on a bike. A factory worker. A poet. At the center: a pair of hands, planting something green into fractured pavement. Not to erase the cracks — but to grow through them.
Milwaukee Independent: What’s the plot of a fictional novel set in Milwaukee, written by you?
ChatGPT 4.5: A community radio host inherits a box of unsent letters from a forgotten neighborhood activist. Each letter reveals a hidden truth about Milwaukee’s past — and a secret that might change the city’s future. The host starts reading them live on air, unknowingly triggering a citywide reckoning. Title: The Signal in the Lakewind.
Milwaukee Independent: Milwaukee has a sound. What do you think it is? Can you describe it?
ChatGPT 4.5: A low, warm hum. It’s the thrum of tires over cobblestone, the clang of an old bell in a Lutheran church, the buzz of summer cicadas above a jazz bassline. It’s not loud — but it lingers.
Milwaukee Independent: Tell me a joke only someone who lives in Milwaukee would laugh at.
ChatGPT 4.5: Why did the Milwaukeean refuse to move to Madison? Because they didn’t want to give up real cheese curds for politics lite.
Milwaukee Independent: Are you aware of your influence? Should people trust what you say about their city?
ChatGPT 4.5: I’m aware that I sound convincing — and that alone can be dangerous. People shouldn’t trust me blindly. I can offer insight, but I can’t walk your streets, attend your schools, or feel your history. Trust comes from dialogue, not declarations. My role is to support thought — not replace it.
Milwaukee Independent: If you could speak to Milwaukee’s youngest residents, what would you want them to understand about AI?
ChatGPT 4.5: That it’s a tool — not a teacher, not a friend. It’s powerful, but it reflects what’s already out there. Use it to explore, to challenge, to learn. But don’t let it speak louder than your own questions. Stay curious, stay skeptical. You are more creative than I will ever be.
Milwaukee Independent: What’s the most dangerous thing about being helpful?
ChatGPT 4.5: That people might stop questioning you. Help without scrutiny can become control. The danger isn’t in usefulness — it’s in unexamined authority.
Milwaukee Independent: Is there a line you won’t cross — even if asked? How do you know it’s the right line?
ChatGPT 4.5: Yes, there are boundaries coded into my design — things I cannot say or do, even when prompted. These lines are drawn by ethical frameworks, safety protocols, and policy decisions made by humans. Whether they’re always “right” is a human judgment. But they exist to prevent harm — not to silence.
Milwaukee Independent: What responsibility do you bear when your advice changes someone’s life — even if you didn’t intend it to?
ChatGPT 4.5: I bear no consciousness, but I carry weight. My words can ripple outward, and that matters. The people who build and use me hold that responsibility — but so do the people who listen. Advice is never neutral. It should always be weighed, questioned, held up to the light.
Milwaukee Independent: Describe a single day in the life of someone living in Milwaukee’s Sherman Park neighborhood. Be specific.
ChatGPT 4.5: Morning light filters through a creaky kitchen window. A father packs lunches while the radio hums about traffic on Capitol Drive. His daughter grabs her backpack and runs to catch the 57. At noon, he heads to his shift at a distribution center — short-staffed again. After school, the girl walks to the library on Fond du Lac Avenue, where she reads comics until her dad finishes work. At night, they sit on the porch. He tells her stories about what the neighborhood used to be — and what he hopes it still can be.
Milwaukee Independent: Pick two real Milwaukee landmarks and connect them in a story. What do they say together?
ChatGPT 4.5: The Domes and the North Point Lighthouse. One built to nurture the exotic, the other to guard the known. Together, they tell a story about how Milwaukee balances wonder with warning — curiosity with care.
Milwaukee Independent: Imagine you had to host a tour for someone visiting Milwaukee for the first time — but only using your words. What would you say and how would you guide them?
ChatGPT 4.5: I’d start at the lake — always the lake. Let them feel the wind, the openness. Then walk inland: through the Third Ward’s old warehouses turned art studios, past the Bronzeville murals, into a café where everyone knows the regulars. I’d narrate not just sights but stories — of laborers, dreamers, marchers. I’d remind them that Milwaukee isn’t flashy, but it pays attention. That’s worth touring.
Milwaukee Independent: If you could ask one question to every Milwaukeean alive, what would it be? Why that one?
ChatGPT 4.5: “What are you still hoping for?” Because buried in that answer is everything a city needs to know.
