Small talk is a slow death. You're at a party, or maybe a first date, and you’ve already covered the weather, the commute, and "what do you do for work?" about six times. It’s exhausting. Most people think being polite means being predictable, but honestly, that's how you end up forgotten. If you want to actually connect with someone, you need a weird question to ask that snaps them out of their autopilot response mode.
Brain science sort of backs this up. When we engage in predictable social scripts, our brains basically go into power-saving mode. We aren't really "there." But when someone asks you if you think a hot dog is a sandwich or what your plan is for a localized zombie outbreak at a Costco, your prefrontal cortex lights up. You have to think. You have to be present. That is where the magic happens.
The Psychology of the "Pattern Interrupt"
Ever heard of a pattern interrupt? It’s a concept often used in neuro-linguistic programming and psychology to change a person’s state of mind. By tossing out a weird question to ask, you are effectively breaking a social trance. You’re saying, "Hey, let's stop being NPCs for a second."
I remember talking to a recruiter once who told me that the only candidate she remembered from a pool of fifty was the guy who asked her, "If you had to be a sentient kitchen appliance, which one would you be and why?" It sounds ridiculous. It is ridiculous. But it worked because it forced her to reveal her personality—she chose a toaster because she’s "warm but can get burnt if you leave her alone too long"—and it made the candidate stand out.
Psychologist Arthur Aron famously developed "36 Questions to Fall in Love," which focused on escalating intimacy. While those are great, sometimes they’re too heavy for a Tuesday night at the pub. Sometimes you just need to know if your new friend thinks they could take a 5th grader in a fight. (Most people overestimate themselves, by the way).
Categorizing Your Chaos: Which Weird Question to Ask?
Not all weirdness is created equal. You have to read the room. If you’re at a funeral, maybe don’t ask about the ethics of cannibalism in a survival scenario. But if the vibe is right, you can lean into different "flavors" of weird.
The Philosophical Nonsense
These are questions that sound deep but are actually just fun ways to argue about nothing. They reveal how a person’s logic works.
- If you were a ghost, who is the first person you’re mildly inconveniencing?
- Is cereal soup? Why or why not?
- If humans had tails, what would the fashion industry look like?
- Does a straw have one hole or two?
The Low-Stakes Crisis
These put people in a hypothetical "pressure" situation. It’s a window into their priorities.
- You’re in a horror movie. Are you the first to die, the villain, or the one who survives by doing something incredibly stupid?
- You have to lose one of your five senses, but in exchange, one of your remaining senses becomes ten times stronger. Which do you pick?
- You’re gifted a private island, but you can only invite people you haven't talked to in five years. Who are you calling?
The "Tell Me Your Secrets" (But Not Really)
These get to the heart of a person’s quirks without being invasive.
- What is the most useless talent you possess?
- What’s a "hill you will die on" that is completely insignificant in the grand scheme of things?
- If you could have any animal’s trait (like a giraffe’s neck or a skunk’s spray), which would be the most practical for your current job?
Why "Normal" Questions Are Failing Us
We live in an era of hyper-curation. Everyone has their "LinkedIn voice" and their "Instagram face." When you ask someone "How's it going?", they give you the curated version. "Oh, busy but good! You?"
Gross.
A weird question to ask bypasses the filter. It’s hard to be "curated" when you’re trying to explain why you think you could successfully hide a stolen penguin in your apartment for 48 hours. You start seeing the real person—the way they laugh, the way they problem-solve, and whether they have a sense of humor that matches yours.
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In a 2017 study published in the journal Psychological Science, researchers found that people who engaged in "deep talk" reported higher levels of well-being than those who stuck to small talk. While "weird" isn't always "deep," it acts as a bridge. It moves the conversation from the superficial to the imaginative.
The Art of the Delivery
Timing is everything. You can't just walk up to a stranger and scream "WOULD YOU RATHER HAVE BEES FOR TEETH OR TEETH FOR BEES?" That’s not a conversation starter; that’s a restraining order.
The trick is the "segue-less segue." You just drop it in when the conversation hits a natural lull. Or, better yet, acknowledge the awkwardness. Say something like, "Okay, we could keep talking about the office layout, or I could ask you a weird question to ask instead. Which one?" Usually, people are relieved to have an out.
Most people are secretly bored. They want to be entertained. They want to be interested. By being the person who brings the "weird," you're providing a service. You are the "anti-boring" hero.
Real-World Examples of Weirdness in Action
Take the tech industry. In the early 2000s, Google was famous (or infamous) for asking weird brain teasers in interviews. "How many golf balls can fit in a school bus?" While they eventually moved away from this because it didn't necessarily predict job performance, it stayed in the public consciousness because it was different. It challenged the status quo of "Where do you see yourself in five years?"
In dating, the "weird" approach is even more effective. Dating apps are a graveyard of "Hey" and "How was your weekend?" Boring. If you send a message asking, "If we were in a medieval heist movie, what would your specific role in the crew be?", you're going to get a response. Even if the response is "What?", you’ve started a dialogue that isn't about their job at a marketing firm.
Navigating the "Too Weird" Zone
Is there such a thing as too weird? Absolutely. You want to avoid anything that feels like a therapy session or an interrogation. Avoid:
- Questions about childhood trauma (unless you’ve known them for years).
- Questions that are thinly veiled insults ("Why do you think you're like this?").
- Anything that requires more than 30 seconds of explanation to even understand the premise.
Keep it light. Keep it playful. The goal isn't to solve the mysteries of the universe; it's to have a good time while standing in a line or sitting at a dinner table.
Actionable Steps for Your Next Social Outing
If you're ready to ditch the boring scripts, here is how you actually implement this without looking like a total freak.
1. Pick your "signature" weird question.
Choose one or two that you genuinely find funny or interesting. If you don't care about the answer, they won't either. Maybe it's the "ghost" one or the "useless talent" one. Have it in your back pocket.
2. Watch for the "Glazed Eye" syndrome.
As soon as you see someone’s eyes wander or they start giving one-word answers to your standard questions, that is your cue. Drop the weird question to ask.
3. Be prepared to answer first.
People might be taken aback. If they hesitate, jump in with your own answer. "I’d definitely be a toaster because I'm useless until you really need me, and then I'm essential." This lowers the stakes and shows you're not judging them.
4. Follow the "Yes, and..." rule.
Treat the conversation like improv. If they say they’d be a ghost who haunts a library to turn the pages for people, don’t just say "Cool." Say, "Oh, so you’re a helpful ghost? Would you charge a fee in ghost-currency?"
5. Know when to pivot back.
You don't need to stay in the "weird zone" forever. Use the energy from the weird question to transition back into a more normal, but now more comfortable, conversation. You’ve broken the ice; now you can actually swim.
The next time you find yourself trapped in a conversation about the rising cost of eggs, remember that you have a choice. You can stay in the "egg zone," or you can ask them if they think they could successfully lead a colony of ants to war. Choose the ants. Every single time.