There Are Questions We Never Ask. I Built Something That Does.
I was twelve when I discovered Gregory Stock’s The Book of Questions. I remember sitting cross-legged on my bedroom floor, thumbing through those pocket-sized prompts — “If you were locked in a time machine set for a single one-way trip to the past or future and had 10 minutes to dial in the time and place, when and where would you go? Why?” — feeling like I’d found a skeleton key to interesting conversation. It wasn’t about the answers; it was the sudden vulnerability, the shift from mundane pleasantries to something that mattered.
Decades later, I found myself craving that again. Not the book specifically, but the friction of it — the way a well-placed question can stop time and force you to actually look at the person across from you.
So I started building.
First Attempt: The Card
I began with utility. I sketched out some questions, wrote contexts for the AI (Gemini, in this case), fed it the emotional texture I wanted — questions that weren’t icebreakers, but ice-melters. Things you don’t ask because they require too much floor space, too much silence to answer properly.
The interface was clean. Card-based. Swipe-friendly. It worked. You could select your context — Close Friend, Stranger, First Date — and the questions would shift tone accordingly. Same emotional depth, different entry ramps.
But… it felt like a boring productivity app. And these weren’t productive questions. They were the kind you ask at 2 AM when the party has thinned out, or during a long drive when the bluetooth audio mysteriously stops working.
The Pivot: Atmosphere as Interface
I realized the container was betraying the content. If the questions lived in fog, in rain, in that specific liminal glow of a streetlight through a window at midnight — then the interface needed to feel like that.
I switched to Claude and got specific. I wanted something retro… almost medieval, but at the same time, deeply emotional. Orbs, magic, ominous undertones, but for existentialism. Pixel art and low-poly geometry, not as nostalgia bait, but because there’s something honest about limited resolution — it forces abstraction, imagination, filling in the gaps.
Just like a good question does.
The visual system emerged organically:
- Curious mode: Rain and fog, something shadowy in the backdrop, the dark blues of insomnia.
- Stranger/First Date: Fiery embers, a glowing presence in the background, the uncertainty of distance — questions that bridge the gap without forcing proximity.
- Solo/Contemplation: Deep water, pressure, bioluminescence — questions meant for journaling, not speaking.
Each mode isn’t just a skin. The animations, the silence, the pace at which text reveals itself, and the name of the character — it all now combines into a much more immersive experience.
What Surprised Me
The AI generation exceeded my expectations, but not in the way I expected. I thought I’d get a polished UI kit. Instead, I got intention — Claude understood that the pixelation wasn’t decorative, that the rain wasn’t ambiance. They were emotional prosthetics, scaffolding to help users access parts of themselves that usually stay guarded.
I still had to hand-tweak. The timing of the text crawl, the specific shade of phosphor-green that feels nostalgic without being cloying, the decision to forego the “Next Question” button and instead just have the user interact with the orb— those were human calls. But the architecture, the vibe? The machine got it.
Where It Lives Now
The result sits somewhere between a game and a ritual. You don’t win. You don’t accumulate points. You just… access the conversation you actually wanted to have.
Some questions are heavy (“What’s something you consider unforgivable that you’ve done anyway?”). Some are playful but pointed (“What are you currently pretending not to know?”). All of them assume you’re ready to stop performing and start being present.
I built it because I missed that feeling from my bedroom floor as a young kid — the shock of real talk. But also because, as adults, we sometimes forget to make space for those moments. We wait for them to happen organically. We forget that sometimes you need to turn off the lights, put on the rain sounds, and ask the thing you’re not supposed to.
You can check out the Obol the Ponderer in all its wonderful glory here.
I’ve written more on the ups and downs of vibe coding and using AI to quickly create powerful prototypes. Here are some posts you might enjoy reading:
