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On your first date? Often, it happens before the food arrives you’re sweating bullets. You’re glancing around the room for something to comment on while sipping your drink in silence and hoping that the other person brings up something you can talk about.

If not, you’re in for a long, dreary night of glancing at your watch! But don’t worry! These weird funny questions to ask can kick-start conversations and maybe even help you bond and learn more about each other. You’ll be able to judge whether it’s a go or no-go after the first date.

Break The Ice With Weird Questions

Since you can’t just fire weird questions to ask guys or at your date out of the blue. Give them a proper heads-up, warn them or they might worry about your sanity. On the other hand, if they outright refuse, you will know they’re no fun.  Maybe you should just get that check right away.

What’s the most underrated movie of all time?

Because we need to start with something easy and “What’s your favorite movie?” is boring, ask about an underrated movie.  It’s the same question with a twist.  Now, you’re asking them to defend the movie of their choice.

Why do this?  Well, no reason other than it’s cute to see the passionate side of someone early into the date. Even if they pick an obscure movie you’ve never heard of, at least the conversation will flow for the next five minutes while they explain it to you.

What’s one thing that everyone loves but you can’t stand?

This is tricky requiring tact to answer because they don’t know what your taste is and whether they will offend you by their reply or not. These maybe weird questions to ask a girl but it can sometimes reveal hidden values and beliefs you will never discuss until later.

What’s the most traumatizing thing you saw on TV when you were a kid?

Everyone’s gotta have an answer to this question. For many of the Baby Boomers, it was Chain Saw Massacre. Mine’s a cat cartoon that started out innocent enough but ended in a splendid gut-spilling bloodbath.

I must caution – of all the weird questions to ask people, this almost always ends with you talking about gross things. But what better way to break the ice than talking about silly things that scared you as a child and having a laugh together?

Little known fact: The more averse to gross things someone is, the more conservative they are.

What’s the most annoying pet peeve you’ve heard of?

During the conversation, you will end up talking about your own pet peeves, which is always fun. It’s always good to get out of the way early so there will be no pointless fights down the road! This is really not one of the weird questions to ask your boyfriend, but it’s a good question. 

Would you rather humanity be fighting vampires, werewolves, zombies or aliens?

Then ask them to explain their choice! Personally, I’d go with werewolves any day, because you only need to get everybody to lock themselves up every full moon and things will be dandy again the next morning.

Totally manageable, right? While this may seem like a total fluff question, you’d be surprised how easy it can lead to philosophical debates about the nature of humanity!

If you could have one lame superpower, what would it be?

The key here is lame – that means no flying, no being invisible, no laser beams from eyes, no controlling the elements. Only un-epic things like avoiding paper cuts or the ability to do the dishes are legal! 

For me, I’d love the ability to threaten ants to leave my food alone so I won’t have to kill them.

What do you wish you invented?

Please don’t say the iPhone! Everyone wants to have invented the iPhone unless they’re a Google, fan, then their answer would be Google. No, be more creative, please!

Bonus points if it’s neither Google or the iPhone and if they don’t even have to think before answering. For more artsy people, change the last word to ‘created’.

If you win the Nobel Prize, what would you like it to be for?

Now is the chance to see if your date cares about anything. World peace? Climate change? A cure for cancer? Black hole theories? This question makes the science/humanities divide clear.

By asking random weird questions to ask people is also a good way to gauge how important fame and success are for them and opens possibilities to discuss future goals and dream careers.

If you could relive one event for fifteen seconds, what would it be?

Anything is possible, from watching the Big Bang to witnessing your own birth – although I do not understand why anyone would ever want to witness their own birth! Haven’t we learned from that birth video already?

What do you wish they had taught you in school?

You can learn a lot about someone by inviting them to preach! While life lessons are always worth hearing, how they’re delivered can be telling: forceful and patronizing, or self-effacing and humble.

This question is not only about what their answer is, but also about how they answer, which might help you see if there’s a red flag ahead!

Pick between having millions and the ability to teleport

This is a practicality test. There’s no right answer. Choosing to have unlimited amounts of money doesn’t always mean you’re shallow because you can do more with more money. People who choose to teleport are more idealistic, but can also be more self-absorbed.

The interesting thing is people have a gut reaction to this question, and it will be helpful to compare your gut reaction to your date’s since it might help reveal a fundamental compatibility issue right off the bat.

Don’t forget to try these weird questions to ask friends with family members, too!


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Mikki Donaldson is a southern girl, born in “hard time Mississippi.” She, like her town, has seen many hurricanes, but bounce back each time. Mikki is no different from any other person with a passion, late to bed and early to rise. The writer adores her family and seeks to leave her mark on this remarkable world.