65 Random Questions To Ask To Get To Know Someone Better

When you’re getting to know someone, there are of course the standard set of questions you ask them. You learn how old they are, what their hobbies are, their favorite foods, TV shows, and movies. At this point you probably know them pretty well, right? Unless you know whether they taste soap or delicious freshness when eating cilantro, or who their favorite high school teacher was, there’s always a selection of random questions to ask to get to know someone even better — plus, they make great conversation starters.

Remember that texting game “20 Questions”? Well, it turns out it’s a lot more useful than just a way to pass the time when you’re bored. You can arguably learn more about a person through seemingly random questions like “ketchup or mustard?” than you can by asking what their five-year plan is. By the time you rifle through 20 playful questions of the not-so-serious stuff, you’ll know too many bizarre facts about this person to call the relationship anything but intimate.

Even Instagram gets it. The “Questions” Stories feature has users posting stickers telling their followers to ask them questions about anything under the sun. Maybe a Story pops up on your feed with an “ask me anything” sticker, or you’re texting someone and trying to learn things about them that no one else knows — in any case, having an arsenal of random questions to ask comes in handy when you’re trying to get to know someone. From the light-hearted and hilarious, to the creative and juicy, here are 65 of the best random questions to ask someone. You’ll learn more than you’d ever expect.

Funny Random Questions To Ask

1. If you could live a day as any type of animal, what would you choose and why?
2. What is the silliest thing you’ve ever done?
3. What is the least amount of money you’d accept to eat a spider?
4. If you could only use five words for the rest of your life, what would they be?
5. How did you find out Santa wasn’t real?
6. What’s the grossest food combination you secretly love?
7. How many unposted TikTok drafts do you have?
8. What movie can you recite every line to?
9. What is the last photo on your camera roll?
10. Would you swallow hair from the shower drain for $5,000?
11. What’s your most repeated movie quote or phrase?
12. What condiments do you put on your hot dog?
13. What is the funniest commercial you’ve ever seen?

Deep Random Questions To Ask

1. If someone narrated your life, who would you want to do it?
2. Who would you want to trade lives with?
3. What was the highlight of your childhood?
4. What is a hobby you want to get better at?
5. If you had three wishes, what would you wish for?
6. What was your favorite children’s book?
7. What would you want done with your body after you die?
8. What’s a favorite memory you have from the past year?
9. If you could redo one moment of your life, what would it be?
10. What do you think happens when we die?
11. What are your most bizarre phobias?
12. If you could only watch one genre of movies the rest of your life, what would it be?
13. How long does it take you to decide if you like someone or not?

Imaginative Random Questions To Ask

1. If you ran for president, what would be your campaign slogan?
2. What food smells way better than it tastes?
3. What is the most important lesson you learned in school?
4. What’s your worst habit?
5. If you could talk to any animal, what would it be?
6. What is a product you cannot live without?
7. Where is your favorite place you’ve ever been?
8. Who is your favorite Disney villain?
9. What’s your most useless talent?
10. If you could ask your pet one thing, what would you ask?
11. If you could change your name, what new name would you pick?
12. What activity do you waste the most time on?
13. What’s your favorite fast food restaurant?

Conversation-Starting Random Questions To Ask

1. What is your Hogwarts house?
2. What is the best card game?
3. What is the worst thing you’ve ever eaten?
4. Who is your favorite TikToker?
5. If you could have a super power, what would it be?
6. What was the last thing you lied about?
7. What is the most useless animal on the face of the earth?
8. What are your weirdest superstitions?
9. What app would you invent if you could?
10. What’s something you think is totally overrated?
11. What’s something you think is totally underrated?
12. What’s a trend you swore you’d never hop on, but eventually did?
13. What country would you most like to visit?

Random “Would You Rather” Questions To Ask

1. If you could time travel, would you go to the future or the past?
2. Would you rather lose an ear or a finger?
3. Would you rather vacation somewhere with a beach or mountains?
4. Would you rather drink hot coffee or iced?
5. Would you rather eat sweet foods or salty foods?
6. Would you rather have good looks or brains?
7. Would you rather be a character from Harry Potter or the Marvel Universe?
8. Would you rather be able to sing really well or dance?
9. Would you rather go to space or explore the deepest parts of the ocean?
10. Would you rather never be able to cut your fingernails or toenails?
11. Would you rather always smell like B.O. or have to smell B.O. on everyone else?
12. Would you rather never have to use the bathroom again or never have to sleep again?
13. Would you rather always be hungry or always be thirsty?