Regardless of how long you’ve known your friends, there are going to be times when conversations lull, and it’s best to have some questions ready for when they do.
Whether you want to dig a little deeper into their inner workings, or just want to inspire some fun, lighthearted conversation, we have questions for every occasion.
- Fun questions to ask friends when bored
- Weird questions
- Funny questions to ask your best friend about yourself
- Group of friends
- New friends
- Fun psychological questions
- Funny truth or dare questions
- Random fun questions
- Fun, deep questions
- Pop culture questions
- Fun would you rather questions
Fun questions to ask friends when bored
We don’t get to connect with friends all the time, so when we spend time with them we want to make the most of it. Keep your conversation entertaining by asking your friends the following 16 questions.
1. If you could have done anything you wanted today, what would your day look like?
 
2. What was the highlight of your day today?
 
3. What was your first impression of me?
4. What’s the most beautiful place you’ve been?
 
5. If you could time travel, would you go to the future or the past?
 
6. What’s your favorite childhood memory?
7. Would you rather be rich and sad or poor and happy?
 
8. What’s the perfect age to get married?
 
9. What would you do if you were invisible for the day?
10. If you could time travel, would you go to the future or past?
 
11. What’s your favorite childhood memory?
 
12. What famous person would you want to have dinner with?
13. What’s your dream pet?
 
14. Do you have any regrets?
 
15. If you were going to compete in the Olympics, what would it be for?
16. What’s your craziest travel story?
 
17. On a scale from 1-10 how basic do you think I am?
Weird questions to ask your friends
If you want to find out which of your friends match your level of weirdness, you can try asking them one of the following 25 questions.
1. Would you still be friends with me if I was a worm?
 
2. How would you get rid of a dead body?
 
3. What do you think animals think about all day?
4. If aliens came to abduct you, would you want to go?
 
5. Do you ever talk to yourself? If yes, how often?
 
6. What movie do you wish you could forget and rewatch for the first time?
7. What’s your favorite smell?
 
8. Was Leonardo Dicaprio really crazy in “Shutter Island”?
 
9. Are you more of a fruit or vegetable?
10. What’s your favorite time of the day?
 
11. Be honest, how long does the 5-second rule really last?
 
12. If you could choose one animal to be able to speak to, what would it be?
13. What color is a mirror?
 
14. Is time ever actually wasted?
 
15. Would you actually want to be able to read minds?
16. How do you feel about aliens?
 
17. What’s your favorite possession and why?
 
18. How seriously do you take tarot readings?
19. If you could go back to high school, would you?
 
20. What’s your favorite word in another language?
 
21. Which celebrity do you think you would be best friends with?
22. If you had to change your name, what would you change it to?
 
23. Which Hogwarts house would you want to be in, and which would you realistically get chosen for?
 
24. How sad would you be if bananas became extinct?
25. What’s your favorite Tik Tok trend?
Funny questions to ask your best friend about yourself
Get ready to enjoy a hilarious conversation with your best friend. These questions about yourself can help you to figure out how your friends see you and their favorite parts of your friendship.
1. What do you consider my worst dating decision?
 
2. Do you see me as more of a cat or a dog, and why?
 
3. When we met, did you think we would become best friends?
4. What word would you use to describe me?
 
5. Who was your least favorite of my boyfriends or girlfriends, and why?
 
6. How would you describe the perfect man or woman for me?
7. What do you think is the biggest gap in my knowledge?
 
8. How long would I last on ‘Survivor’?
 
9. What kind of alcoholic beverage am I?
10. How surprised would you be if I left the country tomorrow?
 
11. Which of the elves in ‘Snow White’ do you think I’m most like?
 
12. What celebrity do you think I’m most similar to?
13. How toxic do you think my dating habits are?
 
14. How would you describe me to one of your other friends?
 
15. What do you think is my spirit animal?
16. Do you think I cry too much?
 
17. What job do you think I would be horrible at?
 
18. What Disney princess do you think I’m most like?
19. Which of “The Office” characters do you think I’m the most similar to?
Questions to ask a group of friends for fun
Asking some of the following funny group questions can help you keep your friends laughing next time you hang out. These questions can prompt some fun answers, and can keep the conversation flowing naturally.
1. If you started a Youtube channel, what would it be about?
 
2. Who here would you not let date your daughter or son?
 
3. What qualities in the opposite sex give you ‘the ick’?
4. Who’s the most likely to get famous?
 
5. Would you rather be the funniest or smartest person in a room?
 
6. If you could have a lifetime supply of any one thing, what would you choose?
7. Are there any star signs you won’t date?
 
8. Would you rather never sleep again or never eat again?
 
9. What’s your worst habit?
10. Are there any songs that you’ve listened to hundreds of times? If yes, which ones?
 
11. What is one random fact that none of us know about you?
 
12. What’s your most prized possession?
14. Who’s your Hollywood crush?
 
15. What’s the best book you’ve ever read?
 
16. Who here would you want to date?
17. Who’s the most likely to get arrested?
Fun questions to ask new friends
When it comes to meeting a new friend, asking basic questions is a great place to start. You can ask a new friend simple questions about family and their childhood, as well as some fun questions to help you connect more deeply.
1. What’s your favorite thing about where you grew up?
 
2. Who in your family are you the closest to and why?
 
3. If you could have any job, what would you choose?
4. If you wrote a book, what would it be about?
 
5. Did you go to school for anything?
 
6. Are you in a relationship, happily single, or somewhere in between?
7. If you could become an expert in one thing overnight, what would you choose?
 
8. Would you rather have a live-in chef or massage therapist?
 
9. If you could choose to live anywhere in the world, where would it be?
10. If you’re traveling, would you stay at a quaint Airbnb or a 5-star resort?
 
11. How do you choose a new restaurant to eat at?
Fun psychological questions to ask friends
The following questions are deep, but lighthearted enough to still keep conversation fun. Asking your friends the following questions will allow you to better understand them and how they see the world.
1. Would you ever want to be famous? If yes, for what?
 
2. Do you feel awkward standing on the bus?
 
3. How weird are the conversations you have with yourself?
4. Do you ever think about how weird it is to be alive?
 
5. What do you think would be the worst way to die?
 
6. If you could see into the future, would you want to?
7. If you could be really good at one thing, what would you want it to be?
 
8. What do you value the most in your life?
 
9. If you knew you were gonna die in 6 months, would you keep your life the same?
10. Do you think there is anything that’s too serious to joke about?
 
11. Do you ever do something and think to yourself, “I’m exactly like my mom/dad”?
 
12. Would you ever want to be the opposite sex? Why or why not?
13. Do you think it’s possible to change your personality?
 
14. How do you feel about your bad habits?
Funny “truth or dare” questions for friend
Questions games can be an amusing way for you to get to know your friend.. Some of these questions might put your friends in the hot seat, but they are a great addition to any game of truth or dare.
1. When was the last time you wet the bed?
 
2. What’s something you’re glad your mom doesn’t know about you?
 
3. Have you ever cheated on someone?
4. Meanest thing you’ve ever done to another person?
 
5. Do you have any fantasies?
 
6. Worst date you’ve ever been on?
7. What’s the most embarrassing thing you’ve ever done drunk?
 
8. Who in this room do you want to kiss?
 
9. Have you ever been arrested? If yes, for what?
10. When’s the last time you lied?
 
11. Have you ever accidentally hit something with your car?
 
12. What would you do if you knew you wouldn’t get in trouble for it?
13. Weirdest thing you’ve ever done in front of a mirror?
 
14. What’s the age of the oldest person you’ve dated?
 
15. What’s the most days in a row that you’ve worn the same pair of underwear?
Random fun questions to ask friends
Asking “yes or no” questions isn’t a great way to keep a conversation going. To spark some deeper conversation you can try asking one of the following 11 questions.
1. What’s the first memory you have?
 
2. Did you ever try to find the pot of gold at the end of a rainbow?
 
3. Who is the coolest person you’ve ever met?
4. How do you feel about spending time alone?
 
5. What’s your favorite way to spend a sunny day?
 
6. What book would you want to live inside?
7. Would you rather be able to teleport or fly?
 
8. What kind of dog are you most like?
 
9. Who is your all-time favorite musician?
10. What superpower would you want, and why?
 
11. If someone gives you the wrong order, do you say something or just eat it?
Fun deep questions to ask friends
Although these questions are on the fun side, they are still quite personal and aren’t appropriate to ask new friends. Deepen your relationship with your close friends with the following deep questions.
1. Does social media make your life better or worse?
 
2. What’s the best piece of advice you’ve ever been given? Did you listen?
 
3. Do you feel like you make the most of every day?
4. What’s your favorite part of your life right now?
 
5. How do you really feel about your in-laws?
 
6. What is a quality in someone that you can’t stand?
7. Are there any parts of your personality that you would never want to change?
 
8. On a scale from 1-10, how childish do you still feel?
 
9. Who are some of your biggest inspirations?
10. Are you good at sharing?
 
11. What job do you think you would be amazing at?
 
12. How do you picture your perfect day?
13. What do you think is the meaning of life?
 
14. Do you value spontaneity or stability more?
 
15. Is it important to you that your partner is funny?
16. What was your favorite animal growing up, and why?
Pop culture questions to ask your friends
The following questions are just for fun and probably won’t spark a deep conversation. Spice up your next sleepover with some pop culture trivia.
1. What are the names of Kim Kardashian and Kanye West’s kids? North, Saint, Chicago, Psalm
 
2. How many times did Ross get divorced on “Friends”? 3 times
 
3. What does the acronym “smh” stand for? Shake my head
4. How many Harry Potter movies are there? 8 movies
 
5. What day is “Star Wars” day? May 4th
 
6. What’s Rihanna’s real name? Robyn Fenty
7. What series is “Baby Yoda” from? The Mandallorian
 
8. Who is the godmother of Miley Cyrus? Dolly Parton
 
9. What fictional newspaper does Carrie Bradshaw from “Sex in the City” write for? The New York Star
10. What is Britney Spears’ most successful song? “Baby One More Time”
Fun would you rather questions to ask friends
Similar to “this or that,” “would you rather” questions are fun and easy questions to ask your friends. They are great conversation starters for groups, and can be used to spark up a conversation with a friend.
1. Would you rather have more time or money?
 
2. Would you rather be able to talk to animals or know every language?
 
3. Would you be sadder if no one showed up to your wedding or funeral?
4. Would you rather go camping or stay in a 5-star hotel?
 
5. Would you rather be beautiful or smart?
 
6. Would you rather be respected or well-liked?
7. Would you rather be single and wealthy for 10 years or poor and in a relationship?
 
8. Would you rather ride in a spaceship or submarine?
