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151 Funny Questions to Ask a Guy Over Text & In Person

Conversation Skills

151 Funny Questions to Ask a Guy Over Text & In Person 50 Funny Questions Inspired by "151 Funny Questions to Ask a Guy Over Text & In Person"

Hey everyone! So you want to get a guy talking and laughing? Asking funny questions is the best way to break the ice and get to know someone. I've been around the block a few times when it comes to school, and trust me, these questions are gold! Whether you're texting or hanging out in person, these will get some good laughs going.

General Fun & Quirky:

If you could have any superpower, what would it be, and what's the first thing you'd do with it?
What's the most embarrassing song you'd sing at karaoke?
If you could have dinner with any three people, living or dead, who would they be and why?
What's the most ridiculous thing you've ever done in public?
What's your go-to pick-up line? (Bonus points for creativity!)

Food & Beverage:

What's the most bizarre food you've ever eaten?
If you had to choose between pizza and tacos for the rest of your life, which would you pick?
What's your ultimate guilty pleasure food?
What's the weirdest combination of food and drink you've ever tried?
What's your favorite way to eat cereal? (Milk first, last, or all at once?)

Travel & Adventure:

What's the strangest place you've ever been?
If you could travel anywhere in the world tomorrow, where would you go?
What's the most spontaneous thing you've ever done?
What's the most ridiculous souvenir you've ever bought?
If you could live in any fictional world, where would you choose?

Pop Culture & Entertainment:

What's the most embarrassing movie you've seen in theaters?
If you could be a character in any movie, who would you be?
What's the most ridiculous TV show you've ever watched?
What song do you sing in the shower?
What's the worst movie you've ever seen?

Personal & Relationship:

What's your worst habit?
What's your best pick-up line?
What's the most awkward date you've ever been on?
What's the most romantic thing you've ever done?
What's your biggest pet peeve?

Hypothetical & Imaginary:

If you could be any animal, what would you be?
What would your superpower be if you could choose one?
If you could have any job in the world, what would it be?
What's the most ridiculous thing you'd do if you won the lottery?
What's the most unusual thing you've ever dreamed about?

Animals & Nature:

What's your favorite animal and why?
If you could have any pet, what would it be?
What's the most bizarre animal you've ever seen?
What's the most beautiful natural place you've ever visited?
What's your favorite season and why?

Gaming & Hobbies:

What video game are you addicted to right now?
What's the most unusual hobby you have?
What's the most competitive game you've played?
If you could design a board game, what would it be about?
What's your favorite childhood game?

Random & Unpredictable:

What's the most useless talent you have?
What's the funniest thing that's ever happened to you?
What's the most ridiculous thing you've ever believed?
What's the weirdest thing you've ever seen on the internet?
What's your favorite way to waste time?

Selfies & Social Media:

What's your most embarrassing selfie?
What's the most ridiculous meme you've ever seen?
What's the most random thing you've ever posted online?
What's the most embarrassing thing you've ever done on social media?
What's your favorite social media platform?