People are terrible at being human sometimes. Like they don’t know how to light up that spark of curiosity when getting to know someone. They don’t know how to show the goofy or unpredictable side of themselves. So that’s why I experimented with weird questions—questions that are so odd and unexpected that they’re sure to make someone laugh, think, or squirm a little.
As it turns out… they work like a charm.
Below I’ve put together a list of 60 weird questions to ask a guy. Funny, quirky questions that go beyond the typical small talk, but are actually good at digging deep and creating rapport. I’ll divide them into categories so you can easily find what you’re looking for.
Ready to get weird?
60 Weird Questions to Ask a Guy
1. Start With The Funny
Ok, let’s kick this list off with some laughs. Nothing breaks the ice like humor. Weird questions that will make a guy chuckle are great ways to help him loosen up around you.
- If animals could talk, which animal would be the rudest?
- Would you rather fight one horse-sized duck or 100 duck-sized horses?
- What’s the weirdest thing you ate to try to look cool?
- If your life was a meme, what would the caption say?
- Who would win in a fight: Pikachu or Mickey Mouse?
Notice how these questions aren’t super personal but will still reveal his thought process. Does he take everything seriously, or is he able to laugh at himself?
Read also: 50 Random Questions to Ask Your Crush
2. Ask About Childhood Oddities
Kids say the darnest things, right? Childhood is a goldmine of weird stories.
- What’s the worst lie you ever told your parents that somehow worked?
- Did you ever get in trouble for something you didn’t do?
- What household item or furniture did you think was alive?
- Did you used to steal the TV remote after your parents yelled at you?
- What was your favorite imaginary friend called?
These questions are deep AF for being so weird. You’ll learn about his childhood while uncovering vulnerabilities you probably never would have known about otherwise.
Read also: 150 Self-Reflection Questions for Personal Growth
3. Random Preferences
Ok, these questions get kinda bizarre. But you have to admit, preferences can say a lot about a person’s personality.
- Would you rather always have slanty eyes or farty ears?
- If you could only eat food that was one color for the rest of your life, what color food would you pick?
- Comparing airplanes to cars, which one shows off better?
- Would you rather bite your nails or pick your butt?
- If you had the power to make one scent follow you everywhere, what would it be?
Notice how silly these questions are, but the answers can actually tell you a lot about him. What he chooses will show his creativity, his humor, and even some of his deeper quirks.
4. Dive Into “Would You Rather”
Would you rather questions are amazing conversational tools. We already gave you a few, but let’s dive deeper… and weird.
- Would you rather sneeze glitter everywhere you go or cry chocolate teardrops?
- Would you rather have fingers made out of spaghetti or hair made out of spaghetti?
- Would you rather never listen to music or never watch TV/Twitter/Snapchat/etc. again?
- Would you rather only fart quietly or loudly for the rest of your life?
- Would you rather be able to talk to animals or talk to furniture?
These ones are cool because they make him think. And once he gives you his answer, there’s normally a story you can get into or learn more about his answer.
5. Weird “If You Were…”
Odd hypothetical questions are great ways to reveal how a person views the world. They can also lead to some interesting conversations.
- If you were magically transported into a cartoon, which one would you like it to be?
- If there was a creepy-looking cloud that played the theme song to your life every time you walked into a room, what would you like it to be?
- If you discovered an alternate universe portal in your closet, would you peek inside or refuse to touch it?
- If someone forced you to eat one type of food for the rest of your life, what cuisine would you pick?
- Aliens arrive at your doorstep threatening to destroy Earth. You get one chance to say something to the leader. What do you say?
Questions like these reveal creativity and give you insight into his problem-solving style. Curious how he’d answer? Go ahead and ask away.
6. Ask About Embarrassing Stuff
Weird questions can also be strange and awkward. Vulnerability often comes from allowing yourself to be silly or share an embarrassing story.
- What is the stupidest thing you’ve ever done to try to seem cool?
- Did you ever tell someone you loved them by accident?
- What was your most embarrassing crash course in education?
- What’s your most useless talent?
- Have you ever gotten really mad at someone only to find out you were wrong?
The cool thing about these questions? They force him to be real. You’ll see who he truly is if he can crack a smile at himself or share an awkward story.
7. Deep but STILL Weird
Not all weird questions have to be surface level. Some of these will open up doors to more interesting conversations.
- If you had to learn one useless skill, what would it be?
- What’s something you used to believe in that now seems silly?
- If you could erase one memory so you could relive it, how would you want to remember it, what would it be?
- Would you rather be known for doing something absurd or be super successful at something boring?
- If you could only eat weird things for the rest of your life, what would you pick?
Weird questions that make him pause and think. You’ll learn about his values while digging deeper than small talk questions usually go.
8. Questions Based on Pop Culture
Pop culture is gold when it comes to coming up with unique questions. You can learn what he likes and why he likes it.
- If you were stuck in a TV show’s universe for a month, what show would you pick?
- Which celebrity do you think would suck the most at baking desserts in a zombie apocalypse?
- If your life was a movie, who would play you?
- Which villain from a movie/book would you secretly team with?
- Would you rather accidentally kiss an alien or your favorite actor first?
Not only are these questions fun, they can help you learn more about his personality based on what he picks.
9. Flirtatious Weird Questions
Okay, these questions may or may not actually be weird, but they’re great for showing off your flirt game.
- If I asked you to sing your weirdest song in public, would you do it?
- What’s the stupidest thing you’ve done for a girl?
- If you could see anyone’s thoughts for 24 hours, who would you pick?
- What’s the cheesiest line that actually worked on you?
- Would you rather kiss someone in the rain or on a snowmobile?
Slightly naughty, somewhat daring, and great for building sexual tension while keeping things light.
10. Just Plain Weird Questions
Alright, alright, let’s just do this. These are dangerously weird questions that will catch him off guard and reveal his brain’s inner workings.
- If you could replace every single blade of grass on this planet with something else, what would you replace it with?
- Would you rather have a redo button for life or a pause button?
- If you had to live at the bottom of the ocean for a year, what would you do first?
- What object do you secretly believe judges you the most?
- If humans had to hibernate in the winter like bears, which season would you choose?
And there you have it! 60 funny, quirky questions you can ask any guy you come across. Whether he’s your longtime friend, coworker, or you’re crushing hard—don’t be afraid to ask something weird.
Normal conversation is boring and predictable. Throw in a weird question here and there and watch him open up in ways you never thought possible.
FAQ
Q: Can I only use these questions when I’m trying to ask a guy out?
A: Heck no. These work wonders on dates but are also great for conversation with friends, networking, or anything in between.
Q: What if he doesn’t answer honestly or humorously?
A: If that happens, let it roll off your back. Focus on how he answered the question vs. what he actually said. Is he shy? Does he pick serious answers over funny ones?
Q: Should I ask all of these or pick and choose?
A: By all means, pick and choose! There’s no need to interrogate with questions like these. Ask a few here and there and go with the flow.
Q: Won’t asking weird questions make me seem weird?
A: Yes, but in a good way. Just don’t go hogwild with these. Be yourself, throw in a question, and pick up on the vibes he gives you.
Q: Will these help me get closer to him emotionally?
A: Most definitely. Weird questions force people to be vulnerable, share funny stories, and let their guard down. Getting comfortable with craziness usually creates better rapport and trust between people.
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