Small talk is basically the worst. We spend half our lives stuck in those weird, stiff loops of "How's work?" and "Crazy weather, right?" Honestly, it’s exhausting. Most people aren't actually boring, they just have boring scripts. If you want better connections—or even just a weirdly fun Tuesday night—you need a better inventory of random things to ask that actually shake the brain a little bit.
Conversation isn't a performance. It's an exploration.
The Psychology of the "Odd" Question
Psychologists like Arthur Aron have famously studied how specific questions can fast-track intimacy. You've probably heard of the "36 Questions to Fall in Love." It works because it forces people out of their "auto-pilot" mode. When you ask someone about their favorite color, their brain doesn't have to work. They just pull a file from a cabinet. But when you ask something like, "If you had to start a cult, what would the one mandatory rule be?" you're forcing them to build something new.
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That's the secret sauce.
Creativity is linked to dopamine. When you ask something unexpected, you're literally giving the other person a tiny hit of brain chemicals. It’s why we remember the person who asked about our hypothetical heist strategy much more than the guy who asked what we do for a living.
Why Your Current Conversations Feel Like Stale Bread
Most people are terrified of being "weird." We stick to the safe stuff. We talk about the commute. We talk about the rising price of eggs. But safety is the enemy of interest. According to a study published in the Journal of Personality and Social Psychology, people actually enjoy deep conversations with strangers much more than they expect to. We overestimate the "awkwardness" and underestimate the "connection."
Stop being safe. Start being a little bit strange.
Random Things to Ask for Immediate Entertainment
Let's get into the actual meat of it. You need things that work in different settings. You can’t ask your boss about their favorite dinosaur (unless they’re cool), but you can definitely ask your best friend.
Hypothetical scenarios are your best friend here.
Try these:
- If you were a ghost and could only haunt one specific household appliance, which would it be to cause the most mild inconvenience?
- You’re given $10 million, but the catch is you have to spend it all in 24 hours without buying any property or stocks. What’s the first hour look like?
- If you had to be a "character" in a grocery store, like the 'grape sampler' or the 'expired milk hunter,' what’s your vibe?
See how those feel different? They require a narrative. They require a personality.
The Low-Stakes Debate
Some of the best random things to ask involve non-serious arguments. These are "low-stakes" because nobody actually gets hurt, but everyone has an opinion. This is the stuff that fuels 2 AM diner conversations.
Is a hot dog a sandwich? (The National Hot Dog and Sausage Council says yes, but they're wrong). Is cereal soup? Does a straw have one hole or two? These are classics for a reason. They spark a debate that has zero consequences, which is the purest form of fun.
Getting Deeper Without Being "That Person"
There is a fine line between being interesting and being a therapist. You don't want to walk up to someone at a party and ask about their childhood trauma. That’s a vibe killer. Instead, look for "sideways" entries into deep topics.
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Instead of asking "What are you afraid of?"—which is heavy—ask "What's a hill you're willing to die on that is completely unimportant?"
This tells you about their values, their stubbornness, and their sense of humor without making them feel like they're in an interrogation room. You’re looking for the "inner monologue" stuff. Most people have a whole world inside their heads that nobody ever asks about.
Real-world example: I once asked a group of strangers what the most "useless" talent they possessed was. One guy could perfectly mimic the sound of a specific 1990s printer. Another woman could name any 80s power ballad within two seconds of the intro. We spent the next hour trying to prove our useless talents.
Things to Ask When the Vibe is Weirdly Quiet
We’ve all been there. The car ride is too long. The dinner service is slow. The silence is starting to feel heavy. This is where you pull out the "ranking" questions.
- Rank these three things from most to least essential for survival: Cheese, the internet, or air conditioning.
- If you had to delete one social media platform from existence forever, which one goes first and why is it LinkedIn?
- What is the most overrated "classic" movie you’ve ever seen?
The "overrated" question is a goldmine. People love to complain. It’s a bonding exercise. When someone admits they actually hated The Godfather, it gives everyone else permission to share their "blasphemous" opinions.
The "Expertise" Angle
Everyone is an expert in something incredibly niche. Most people never get to talk about it because it doesn't come up in "normal" conversation.
Ask: "What is the one thing you could give a 30-minute presentation on with zero preparation?"
You might find out your accountant is obsessed with the history of salt, or your sister knows everything about the migratory patterns of monarch butterflies. This is how you discover the "hidden" person.
Navigating Social Nuance
You have to read the room. Not every random thing to ask works in every scenario. If you're at a funeral, maybe don't ask about the appliance haunting. If you're at a high-stakes business meeting, keep the "cult rule" question in your pocket.
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Context is king.
In a professional setting, you can still use this technique by slightly pivoting. Instead of "What's your favorite dinosaur?" try "What's the most surprisingly useful thing you've learned from a job you hated?" It’s still a random prompt, but it fits the environment.
The Art of the Follow-Up
The question is just the bait. The follow-up is the hook.
If they answer your question about the haunted appliance with "The toaster," don't just say "Cool." Ask "Why the toaster? Are we talking burnt toast every time, or just popping it up too early?"
Engage with the absurdity.
Actionable Steps for Better Conversations
If you want to stop having boring interactions, you have to be the one to change the frequency. It won't happen on its own. People default to the path of least resistance.
- Keep a "Starter Pack" in your phone notes. Seriously. Just three or four go-to questions for when your brain freezes.
- Listen more than you talk. If you ask a great question, let them run with it. Don't just wait for your turn to share your "funny" answer.
- Pay attention to "Sparks." If you see someone’s eyes light up when they mention a specific hobby or a weird fact, dig deeper there. That’s where the gold is.
- Stop worrying about being "cool." The most interesting people are usually the ones who are okay with being a little bit dorky or curious.
Connection is a skill. Like any skill, you get better with reps. Start small. Ask the barista something slightly off-script. Ask your partner a question you've never asked in five years of being together.
The world is significantly more interesting when you stop asking "How are you?" and start asking "If you were a color, which one would be the most annoying to be?"
Go be a little weird. It’s worth it.