Questions for the Chaotic Neutral

For the last decade or so, I’ve been collecting questions. Good ones. Weird ones. Chaotic ones. Questions that make people stop and actually think instead of giving the usual autopilot responses.

I started out calling them my “Tinder opening lines” because that’s where the idea came from, but they’ve become so much more useful than that. I wanted to be able to differentiate myself quickly and ended up finding a way to connect to people more quickly. These questions have helped me in interviews, in connecting better with team members and friends, while traveling in hostels, surviving awkwardness at dinner parties of disparate groups of people, you name it.

Why I Started This

Most small talk is terrible. It’s predictable, surface-level, and designed to fill silence rather than create connection. The standard questions lead to standard answers, and everyone walks away having learned nothing about each other.

Standard questions are a good place to start to warm people up. And that’s important because these questions often really throw people off (usually in a good way, but not always). But after the warm ups, I wanted something better. Conversations that could cut through the formalities and get to something real and ultimately memorable quickly. Not in an intense or uncomfortable way, just in a way that actually reveals something about who someone is.

So I started collecting them. Every time I heard a question that made me pause, made me think, or got an interesting response, I’d add it to the list. Over time, it grew from a handful to the roughly 50 or so questions that I have now that range from genuinely interesting to completely chaotic.

How I Use Them

The beauty of this list is its versatility. I’ve used these questions:

• When meeting new people, where they’ve saved me from countless “so what do you do?” loops
• At work, to get to know new team members beyond their job title
• In interviews, both as a candidate and as a hiring manager
• At conferences and networking events where everyone’s doing the same tired dance
• With friends when we’re stuck in conversation ruts

I usually just need a single question, let people think a bit and then stay genuinely curious about understanding their answers.

What I’ve Learned

Having this list has changed how I approach meeting people. Instead of feeling pressure to be naturally charming or witty, I just ask a good question and let the conversation unfold from there. The questions do the heavy lifting. It’s also taught me that most people are interesting when you ask them the right things. Everyone has stories, opinions, and quirks that don’t come up in typical conversation. You just need to create the opening for them to share. And honestly, it’s made socializing more enjoyable. When you have a mental toolkit of interesting questions, you’re rarely stuck making boring small talk or scrambling for something to say.

One of my favorite times that these questions have yielded the kind of outcome I wanted, was a few years ago when I was out with a friend in London. I hadn’t seen her in years and after we did the life catch up, I asked her if she could give a TED talk on anything right now with no preparation, what would it be? She proceeded to give me a 15-minute diatribe on the correct and incorrect ways to make a martini and what it says about people who make them in those various ways. It was absolutely fascinating to hear her views and how much thought she’d put into them. We have become much better friends since that evening.

The List

These questions work because they’re specific enough to be interesting but open-ended enough to let people take them wherever they want. Some are lighthearted, some are deeper, and some are just plain weird. That’s the point.

Use them however you want. Pick your favorites. Memorize a few. The goal isn’t to interrogate people or follow a script, it’s just to have better conversations.

While this is only about half the list, these questions are the ones I’ve found to work best in the widest variety of situations:

1. If you were a dragon, what would you hoard and why?
2. What could you give a TED talk on right now with virtually no preparation?
3. If you were a pirate, what would your mascot be and why?
4. If you could have any super power, what would you have and why?
5. If you could be invisible or have the power of flight, which would you choose and why?
6. You’re being sold as an action figure, what 2 accessories do you come with and why?
7. Who would you replace the heads on Mount Rushmore with? Be prepared to explain what Mount Rushmore is to non-Americans.
8. If you could eat ice cream that is flavored like any concept, what would it be? (Eg. Jazz music, going back to sleep on a Sunday morning, checking your bank account with lots of money in it)
9. What are your skills that would aid us in a zombie apocalypse?
10. If you were getting sucked into universe where everything started with the same letter, what letter would it be and why?
11. Would you rather be a pirate, a cowboy, or a samuari? Why?
12. If you could only do 1 action for the rest of eternity, what would that action be?
13. If you could live in any TV show or movie, what would you choose and why?
14. If you could dispense 5 liquids (one from each finger), what would you dispense and why?
15. If you can have dinner with anyone living or dead, who would it be and why?
16. Would you rather have eyes that can film everything or ears that record everything?
17. If time was frozen for 24 hours but you could still move around, what would you do?
18. If you were given 1 hour with an alien and you can ask 3 questions, what would you ask?
19. If your pet suddenly spoke and said just one sentence, what would be the most unsettling thing it could say?
20. If you could “get with” one animated movie character, who would it be and why?
21. Which movie villain (or real life villain) do you most identify with and why?
22. If you could roast any historical figure, who would you roast? Why? And what would you say?

Closing Thoughts

The real value is not in the questions or the answers, but the conversation that follows. While it’s not always easy to get people talking, showing genuine interest in understanding people usually keeps the conversations going. These kinds of questions engender everything from philosophical insights about people’s world views to info-dumping about a niche topic. Pay close attention to the responses so you can follow up and continue the conversation. But be prepared to answer the question yourself. Conversations are a 2-way street and connection is created in both directions.