Weird things I've asked AI

Over the past year, I've asked AI some questions that probably shouldn't be allowed to escape my brain. Some started with genuine curiosity. Others started with something weird I noticed, a random thought that wouldn't leave me alone, or a perfectly normal question that somehow spiraled into something ridiculous.

Here are some of the highlights. You're welcome. Or I'm sorry. I'm not entirely sure which.

Suburban Lumberjack: Hurricane Isaias vs. My Backyard

Hurricane Isaias was supposed to be a direct hit. The early tracks had it coming straight for us, so we did the usual storm routine—move the cars, eye the tall dead pine on the adjacent lot, and mentally rehearse the sound of branches hitting the roof. In the end, the storm shifted east and came ashore closer to Destin, leaving us with wind, some rain, and a very specific kind of suburban chaos.

The AI Warning-Label Challenge

Every now and then, my wife throws me a challenge that is equal parts mischievous and revealing. This time, she hit me with the infamous prompt:

“Describe me like you’re trying to warn someone about me before they meet me.”

Naturally, I accepted — and then escalated it. I ran the prompt through four different AI systems: Copilot, Gemini, Claude, and ChatGPT. What followed was… well, a mix of flattery, psychological profiling, technical audits, and mild character assassination. In other words: a normal Tuesday. (Except it's currently Saturday. I also had Copilot draft this blog post, including the quotes below from each AI. Because it's what I do. Sometimes.)

Below is the full set of responses, presented verbatim, each in its own block. If you’re new here, this is exactly the kind of thing my LBD experiments tend to produce — unexpected, slightly chaotic, and probably something I’ll regret publishing. (Oh, and apologies for the occasional stray moments of enhanced vocabulary in the AI replies - I don't talk that way, even to the AIs, but sometimes they go their own way. I'm just quoting exactly as they replied below.)

I Think I May Have Accidentally Built a Website

It all started because I couldn't find a thimble. Now there's an AI trying to conquer the world and a game where you stab fingers. Naturally.

There is a website called Stab the Finger.

It has subdomains.

It has experiments.

It has an AI research operation.

It has an artificial intelligence attempting to conquer the world.

It has an abandoned social network.

It has a half-built real estate management application.

And, as of very recently, it has a video game in which you stab fingers.

I feel like I should explain how this happened.

The short answer is:

I have no idea.

The slightly longer answer is that it started with a hat.

Dombot Didn't Evolve. It Declared the 90s.

Every time Dombot updates its Master Blueprint, the version numbers get weirder.

Phase 2 quietly syncs an entire family of systems to 11.0. Phase 3 runs three completely unrelated numbers — 5.1, 9.4, 8.7 — like nobody in that department talks to the others anymore. And then Phase 4 just skips straight into the 90s: 95.7, 94.2, 88.9. No buildup. No sequence. No explanation.

Just a fictional AI system that woke up one pass and decided it was in the 90s now.

And that may be the funniest part.

Windows versioning was never about lineage either. It was authority aesthetics — numbers chosen because they felt newer, more official, more inevitable.

3.11 → 95 → NT → 98 → Me → 2000 → XP → 10 → 11.

No logic. No sequence. Just vibes, confidently deployed.

Dombot is doing the same thing.

It's not escalating its systems — it's branding them.

It's not communicating progress — it's performing it.

It's not following a roadmap — it's cosplaying one.

The satire lands harder because the inconsistency is the point: a synthetic overlord inventing version numbers the exact way real institutions do — inconsistently, non-sequentially, and with total confidence that no one will question the jump.

Dombot didn't evolve into the 90s. It declared the 90s. And that's exactly how you know it's working.

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Dombot's Version History (a changelog, of sorts)

If Dombot ever had to file an actual changelog, it would probably look like this:

v1.0 — Initial deployment. Systems have names like "Resource Allocator" and function more or less as described.

v2.0 – v6.4 — [REDACTED FOR BREVITY]. Mostly mitigators mitigating things caused by earlier mitigators.

v6.5 — Simultaneous, unexplained version-lock across five unrelated Phase 2 systems. No changelog entry justifies why they all moved together. They just did.

v9.4, v8.7, v5.1 — Phase 3 stops pretending to coordinate. Three systems, three unrelated numbers, no shared roadmap. Possibly a turf war. Possibly nobody's in charge over there. Unclear.

v11.0 — A full numeric leap with no v7 through v10 ever observed in the wild. Industry analysts (there are no industry analysts) speculate this was a branding decision.

v88.9 – v95.7 — Phase 4 skips the entire 12–87 range and lands directly in "clearly the 90s now" territory. No further explanation offered. None requested.

v∞ (implied) — Eventually, Dombot will ship something called "Directive Diversifier XP" and nobody will blink.