These Totally Random Questions Are The Best Ice-Breakers To Prompt Some Hilarious Conversations, Whether You’re On A First Date Or Meeting New People For The First Time

How many times have you gone out with a new group of friends or sat on a first date with absolutely no clue how to break the ice?
I mean, aside from talking about the weather, what you do for work, and getting into trivial debates about your favorite colors, it can be pretty difficult to get to know someone with little to no background information. Thankfully, though, there is one foolproof way to get to know someone better without having any anxiety or doing any time-consuming social media profile stalking. I’m talking about asking questions.
And not just any old questions, might I add. By breaking out some of the weirdest, niche, and most surprising questions, you will be amazed by the conversation that can start to flow.
First of all, your date or new friend will be totally caught off guard. And depending on the question you ask, there might be some immediate laughter and tangential conversation.
The real benefit of this tactic, though, is that the answers are often just as ridiculous and hilarious as the questions.
Plus, you will slowly start to learn more about the person aside from the boring old facts like where they grew up or what sports they played. Don’t those get old quickly anyway?
Thankfully for you, we have also compiled some of the most random and intriguing questions to ask during your next social outing. All you have to do is commit them to memory and simply let the rapport flow afterward.
Exposing The Junk In Their Trunk
At any point in time, you might have water bottles, old Starbucks cups, scrunchies, chargers, and so much more just floating around the back seat of your car. But when was the last time you cleaned out your trunk?

Flamingo Images – stock.adobe.com – illustrative purposes only, not the actual person
If you are like most people, you probably can’t remember and have a ton of random items hiding back there. So, why not open with a relatable question and revel in some hilarious honesty?
“What’s in the trunk of your car right now?’ This leads to some hilarious answers in my experience.” –Edenunbound
Potatoes, Period
Everyone loves potatoes in one form or another. A mashed potato hater may love french fries, and a waffle fry gal may despise the classic baked potato.
So, this carb can be the perfect way to have a lively debate and figure out your compatibility with others.
“I like to ask, ‘What is your favorite version of the potato?’ Everyone always has a different answer, and they are pretty opinionated about it.” –Ptran99
“Obscure Factoids For $500”
Even if you don’t watch Jeopardy, you know what it is. The theme music alone is arguably one of the most recognizable tunes in U.S. pop culture. On top of that, every single person has at least one weird tidbit of information that is so random and so niche that they never get an opportunity to share it. So, play into that, and give obscure knowledge a chance to shine.
“What’s the most obscure fact you know that would make you win on Jeopardy?” –Unoriginallygeneric
Cheese Please
People who like cheese don’t simply just “like it.” They love it. Plus, if you live near the cheese capital of the United States (Wisconsin, duh), then this question is a surefire way to spark some serious debate.
“If you could only eat one type of cheese for the rest of your life, which type of cheese would it be?” –Tehvolcanic
To Sleep With Socks On Or To Not
Similar to cheese lovers, people who sleep with socks on versus socks off are, in my opinion, two different breeds who have very strong opinions about their sleepwear choices.
This is a great question to get a bit more personal and poke some fun at sock wearers. I mean, don’t they get hot?!
“Do you sleep with socks on, and if yes, how many people have you murdered?” –Cgull21
Get In Their Head
We all have that little voice in our head, known as our conscience. But does everyone experience “it” the same way? Use this question to find out.
“Do you have an internal monologue? Like, do you think in words, images, or some other way? I find it fascinating, and I think it says a lot about a person, how they perceive the world, and how they learn.” –Mysteryof_
Cringey (Yet Relatable) Childhood Memories
Want to get to know more about what someone was like during the god-awful years of middle school without actually asking?
What they listened to while riding the bus home after school will probably tell you everything you want to know.
“What sort of music did you listen to in seventh grade?” –Snoolobgsters9180
Lights, Camera, Action
If you are trying to figure someone out– more specifically, how they view themselves and the general theme of their life– then this question is foolproof. Plus, you can chime in with your own answer and compare your own movie plotlines.
“If Hollywood made a movie about your life, what would it be rated, and who would be the star?” –[deleted]
To read the original Reddit thread, visit the link here.
If true crime defines your free time, this is for you: join Chip Chick’s True Crime Tribe
Tired Of Eating Regular Salad? Try Making This Charred Romaine Instead
Sign up for Chip Chick’s newsletter and get stories like this delivered to your inbox.
More About:Advice