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Random Questions to Ask – 70+ Fun & Great Conversation Starters

Looking for random questions to ask a boyfriend, girlfriend, on a date or even a double date with friends?

To be honest date night can get so boring and it can be hard to think of things to ask after a while. So, why not open this article and make a fun game night with these questions.

Can’t see each other because of quarantine? That doesn’t stop you texting, you could even use these questions as a super fun opener for tinder online dating. To save you some time, we have categorised these questions by type, in case you are just looking for 1 or 2 questions pronto but all these questions can be asked to just about anyone.

The perfect list of random questions to ask people!

Random Questions to Ask – 70+ Fun & Great Conversation Starters

Funny random questions

With so many questions to ask, let’s start off with some funny questions to get the party started. Funny questions are good because they are so lighthearted and entertaining:

Why is it that round pizzas come in square boxes?  

What animal is the biggest party animal?

What is your spirit animal?

Tell me about your worst ever stack/fall?

What is the funniest joke you have heard?

What is something that everyone looks stupid doing?

Would you rather live in a sailboat or in a RV?

What id the most embarrassing thing that has ever happened to you?

Have you ever tried talking to your dog?

Would you ever eat snails?

If animals could talk, which would be the rudest?

Random questions about life

Questions about life in general really help you to get to know someone better, especially if you have just started dating, you can learn more about what they want in their future and what they value:

What if you could live for 200 years?

What was your best age in life so far?

If you could change something about your past what would that be?

Who was your first ever crush?

What were you like in high school?

What is the one thing you hate about your family?

Is your glass half full or half empty?

If you had to listen to one song for the rest of your life, what would it be?

What is the worst thing you’ve done as a kid?

If you could live forever, but that means being a vampire, what you choose to do it?

If you could have any career on the planet, what would it be and why?

What is the worst meal you’ve ever had?

What’s Your Favorite Place on Earth?

Random questions to ask friends

Having a “question party” with friends is so fun. Next time you are with your mates, add these questions to your dinner discussion. Random questions of the day:

If You Had Three Wishes, What Would You Wish For?

What cartoon do you still like to watch?

What’s the weirdest dream you’ve ever had?

What’s the weirdest smell you have ever smelled?

What would your superhero power be?

Are you a folder or a scruncher (I’m referring to tee-pee paper)

What’s the spiciest thing you’ve ever eaten?

Do you believe in fate?

Do you believe in destiny?

What’s the funniest comedy skit you’ve seen?

What weird food combinations do you like?

If you were a fruit, what fruit would you be?

What’s your favorite book? 

If you could live anywhere, where would you live?

If you could travel to any year in a time machine, what year would you choose and why?

If you could choose only one – would you select love or money?

If you could be any animal, what animal would you choose to be?

What is the best prank you’ve played on someone?

Random questions to ask a girl

What on earth should you ask the girl you like that is random, lighthearted and not too serious. Here are some good ones for ya:

What is on your bucket list?

What’s the craziest thing you’ve done for love?

What’s your favorite television show?

What would you name your boat if you had one?

If you were on love island, describe your type on paper?

Would you rather never be able to go out during the day or never be able to go out at night?

Would you rather lose your sight or your memories?

Would you rather be the first person to explore a planet or be the inventor of a cure?

Would you rather be rich or famous?

What’s your biggest deal-breaker in a relationship?


Random questions to ask a guy

Here are some questions for the boys. Things you have been dying to know, asked in a totally random way:

What’s your biggest deal-breaker in a relationship?

What kind of pillow is your favourite?

What would be your perfect day?

What’s your favorite sports team?

How well do you sleep in hotel rooms?

So, why is it worth taking a chance on you?

Are you a heartbreaker?

Starter, main or desert?

Would you cook for a girl?

Do you think that aliens exist?

Do you think ghosts are real?

Do you think horoscopes are real?

You prefer being the big spoon or the little spoon?

Are you a light sleeper?

What’s the funniest thing you’ve ever seen?

What do you think is the best pick up line?

What do you think is the worst pick up line?

What is the worst pick up line you’ve ever heard?

Random questions to ask your crush

Talking to your crush can be hard. Here are a few random conversation starters to ask your crush over tinder or even via text:

What do you think is my favorite food?

Do you prefer city or country?

What’s the best type of cheese?

If I was a flower, what kind of flower would I be?

Do you like huge parties or would you rather spend time in a small group?

Are you a planner or are you more of a spontaneous person?

Do you prefer apples or oranges?

Could you become a vegan?

Did you like science in school?

What was the last photo you took?

Weirdest passion you have?

What color do you think would look best on me?

What is something that you think sets me apart from other people?

If money were no option, where would you live?

Strangest habit you have?

What famous actress do you think I’m most like?

What’s the weirdest flirty text you’ve ever received?

Random questions to ask your boyfriend/girlfriend

So you’ve taken it to the next level – good for you. Heres some cool questions just for you.

What would you say is your favorite feature about me?

Name 3 of my body parts that you like the most?

What mythical creature do you wish actually existed?

What was your most recent lie?

What do you dislike most about yourself?

What do you like most about yourself?

Have you stalked an ex on social media?

If we were to go on another date, where would you take me?

What do you like most about yourself?

How do you like to be comforted when you’re sad or upset?

What is the kindest thing you have ever done?

Would you ever go bungee jumping or rock climbing?

What is the proudest moment of your life?

See more Fun questions for Date Night