500 Questions to Ask at a Sleepover

Sleepovers are always a blast! You get to stay up late, eat snacks, and just hang out with friends. But sometimes, when the excitement settles down, you might run out of things to talk about.

That’s when having a list of fun questions can come in handy. Whether you’re looking to get to know each other better, laugh until your stomach hurts, or share some deep secrets, asking the right questions can make the night even more memorable.

So, why not have a few ideas up your sleeve to keep the fun going? Ready to find out the questions that will make your next sleepover the best one yet?

Questions To Ask About Friends

1. Who’s your oldest friend?
2. How do you make new friends?
3. What do you think makes a good friend?
4. Have you ever lost a close friend? What happened?
5. What’s the most fun thing you’ve done with friends?
6. Do you have a friendship you regret?
7. Who’s the smartest friend you have?
8. What do you usually talk about with your best friend?
9. Have you ever had a crush on a friend?
10. What’s the biggest fight you’ve had with a friend?
11. Do you have any long-distance friends? 
12. How do you keep in touch?
13. Have you ever been jealous of a friend?
14. Do you have a friend who’s really different from you? How?
15. Who’s the funniest person in your friend group?
16. What’s the most embarrassing thing you’ve done in front of friends?
17. Do you share secrets with your friends?
18. Have you ever traveled with friends? Where did you go?
19. What’s the best gift you’ve received from a friend?
20. Do you have a friend who always gives good advice?
21. What’s the weirdest thing you and your friends have done?
22. Do you have a go-to friend for different problems?
23. Have you ever helped a friend in a big way?
24. Do your friends like the same things as you?
25. Have you ever had to say sorry to a friend?
26. What do you and your friends do for fun?
27. Do you think friends are more important than family? Why?
28. What’s the nicest thing a friend has done for you?
29. How do you solve problems with friends?
30. What are some inside jokes you have with friends?
31. Do you have any famous or celebrity friends?
32. Have you ever had an online friend you later met in person?
33. What’s the longest friendship you’ve ever had?
34. Do you and your friends have a favorite hangout spot?
35. How do you choose who to be friends with?
36. Do you have a friend who’s a great listener?
37. Have you ever borrowed something from a friend and forgotten to give it back?
38. Do you have a friendship that started in a really unusual way?
39. What’s the most important thing a friend should never do?
40. Have you ever been the “third wheel” with friends? How did that feel?
41. How often do you talk to your closest friends?
42. Have you ever been to a friend’s wedding?
43. Do your friends know your family well?
44. Have you ever had a friend surprise you in a really good way?
45. What’s the farthest you would go to help a friend?
46. Do you have any friends who are really into politics or activism?
47. Have you ever been friends with someone but never met their family?
48. Do you have friends from different cultural backgrounds? 
49. What have you learned from them?
50. Have you and a friend ever liked the same person? What happened?
51. Do you believe in “best friends forever”?
52. What’s the most challenging thing about maintaining friendships?

Questions To Ask About Crushes

1. When did you have your first crush?
2. What’s the most awkward thing you’ve done in front of your crush?
3. Do you believe in love at first sight?
4. Have you ever told a crush how you feel?
5. What’s your dream date?
6. Do you have a “type”?
7. Have you ever had a crush on a fictional character?
8. What’s the most romantic thing someone has done for you?
9. Have you ever had a crush on a friend’s sibling?
10. What’s the longest you’ve ever had a crush on someone?
11. Have you ever been friend-zoned?
12. What’s the weirdest thing you’ve done to get a crush’s attention?
13. Do you believe in soulmates?
14. What’s your go-to flirting move?
15. Have you ever had an online crush?
16. What’s the most important quality you look for in a crush?
17. Have you ever had a crush on a boss?
18. Do you have any celebrity crushes?
19. What’s the biggest age difference you would consider in a crush?
20. Have you ever liked someone but knew it wouldn’t work out?
21. Do you have a crush right now?
22. What’s a deal-breaker for you in a relationship?
23. Have you ever had a secret admirer?
24. How do you deal with rejection?
25. Have you ever had a crush on someone who was taken?
26. What’s the most romantic movie you’ve seen?
27. Do you believe in “the one”?
28. What song reminds you of your crush?
29. Have you ever been caught stalking a crush online?
30. Do you think long-distance relationships can work?
31. What’s the cutest text you’ve ever received from a crush?
32. Have you ever written a love letter? Did you give it to them?
33. What’s the biggest romantic risk you’ve ever taken?
34. Have you ever been someone’s secret crush?
35. Do you believe in love horoscopes?
36. What’s a TV or movie relationship that you wish you had?
37. Have you ever had a crush on someone you met while traveling?
38. What’s the most romantic place you can think of?
39. Have you ever had a crush on a family friend?
40. Do you talk about your crush with your parents or siblings?
41. What’s the most embarrassing thing you’ve ever Googled about love or relationships?
42. What romantic gesture makes you melt?
43. Have you ever had a dream about a crush that felt super real?
44. What’s a talent or skill that you find really attractive?
45. Have you ever pretended not to like someone that you actually liked?
46. What’s a movie quote that sums up your love life?
47. How would you feel if your crush knew you liked them?
48. What’s your ideal first kiss scenario?
49. Have you ever practiced talking to your crush?
50. What’s a piece of love advice that you swear by?

Questions To Ask About Funny Stories

1. What’s the funniest thing that’s ever happened to you?
2. Have you ever had a really embarrassing wardrobe malfunction?
3. What’s the most hilarious text or autocorrect fail you’ve had?
4. What’s the funniest prank you’ve ever pulled or had pulled on you?
5. Have you ever been caught doing something really silly?
6. What’s the most ridiculous rumor you’ve heard about yourself?
7. Do you have any hilarious pet stories?
8. What’s your most embarrassing family moment?
9. Have you ever laughed so hard you cried?
10. What’s the funniest thing you’ve ever said or done in your sleep?
11. What’s the weirdest or funniest thing you’ve done to impress someone?
12. What’s the funniest thing that’s happened to you on a date?
13. Have you ever had a hilarious misunderstanding with someone?
14. What’s your funniest childhood memory?
15. Have you ever accidentally sent a text to the wrong person?
16. What’s the most amusing way you’ve ever quit a job?
17. What’s the funniest thing that’s happened to you at school?
18. What’s the most ridiculous thing you’ve ever believed?
19. What’s the funniest thing you’ve heard a child say?
20. Have you ever been in a really funny or awkward situation with a stranger?
21. What’s the weirdest or funniest thing you’ve found in someone else’s bathroom?
22. Have you ever had a funny encounter with an animal?
23. What’s the funniest thing you’ve ever seen at a wedding?
24. What’s the most hilarious thing you’ve ever seen on social media?
25. Have you ever had a funny cooking or baking fail?
26. What’s the silliest thing you’ve ever done on a dare?
27. What’s the funniest thing you’ve done while bored?
28. What’s the most ridiculous thing you’ve done out of laziness?
29. Have you ever had a funny gym or workout moment?
30. What’s the funniest thing that’s ever happened to you on vacation?
31. Have you ever tried to create a viral video or post that totally flopped?
32. What’s the funniest excuse you’ve ever used to get out of something?
33. What’s the funniest misunderstanding you’ve had while learning a new language?
34. Do you have a hilarious holiday story?
35. Have you ever mixed up someone’s name, and how did you recover?
36. What’s the most awkward gift you’ve ever received?
37. What’s the funniest thing you’ve ever done while sleepy or half-awake?
38. Have you ever gone to the wrong event or party by mistake?
39. What’s the funniest thing you’ve seen someone else do in public?
40. Have you ever done something really silly on autopilot?
41. What’s the funniest thing you’ve accidentally overheard?
42. Have you ever been hilariously caught in a lie?
43. What’s the funniest thing you’ve done out of nervousness?
44. Have you ever mistaken a stranger for someone you know?
45. What’s the silliest thing you’ve convinced someone to believe?
46. What’s the funniest thing that’s happened to you at a job interview?

Questions To Ask About Music

1. What’s a song that always makes you dance?
2. What’s your go-to karaoke song?
3. What’s the first concert you ever went to?
4. What’s a song that always makes you emotional?
5. Do you prefer music festivals or small gigs?
6. What’s the weirdest music genre you enjoy?
7. What’s the most overrated song, in your opinion?
8. Who’s your musical guilty pleasure?
9. Do you have a song that reminds you of your childhood?
10. What’s your favorite line from a song?
11. What’s your favorite music video?
12. What’s a song you can’t stand but can’t get out of your head?
13. Who’s an artist you wish you could see live?
14. What’s a really popular song you actually hate?
15. What’s a song that always makes you feel good?
16. What was the last song you listened to?
17. What’s a song you like to work out to?
18. What’s your favorite song lyric?
19. Have you ever discovered a band or artist before they got famous?
20. What’s your favorite album of all time?
21. Do you play any musical instruments?
22. What’s your favorite live performance you’ve watched online?
23. What’s the most memorable concert you’ve attended?
24. What’s a song you love from a genre you usually don’t like?
25. What’s a song that helps you relax?
26. Do you like to listen to music while you work or study?
27. What’s a song you listen to when you’re feeling down?
28. What’s your favorite one-hit wonder?
29. Have you ever met a musician or band you admire?
30. What’s a song you’re embarrassed to admit you like?
31. What famous song that took you a while to warm up to?
32. What’s your favorite cover song?
33. What’s a song you think everyone should listen to?
34. What’s the best music concert or festival you’ve been to?
35. What’s a song that you think is underrated?

Questions To Ask About Movies

1. What’s your all-time favorite movie?
2. Do you have a movie that you can quote line for line?
3. Have you ever cried during a movie? Which one?
4. Who’s your favorite actor or actress?
5. What’s the last movie you saw in theaters?
6. What’s a movie that everyone loves but you don’t?
7. Do you have a movie that reminds you of an ex?
8. What’s a movie you love but are embarrassed to admit?
9. What’s a movie you could watch over and over again?
10. What’s your favorite movie soundtrack?
11. Who would play you in a movie about your life?
12. What’s the most disappointing movie you’ve ever seen?
13. What’s your favorite Disney movie?
14. What’s a movie that scared you as a kid?
15. Do you listen to any podcasts about movies?
16. What movie do you think everyone should watch at least once?
17. What’s your favorite movie genre?
18. Who’s your favorite movie villain?
19. What’s the best movie you’ve seen recently?
20. What’s your favorite animated movie?
21. Do you prefer watching movies at home or in the theater?
22. Have you ever walked out of a movie because it was bad?
23. What movie do you wish had a sequel?
24. What’s the scariest movie you’ve ever seen?
25. What’s a film that made you laugh until you cried?
26. Have you ever seen a movie more than three times in the theater?
27. Who’s your favorite movie director?
28. What’s your favorite movie quote?
29. What movie has the best special effects, in your opinion?
30. What’s a film that you think is overhyped?
31. What’s the worst movie adaptation of a book you’ve seen?
32. What’s your favorite romantic movie?
33. What’s a movie that always makes you cry?
34. What’s a movie you love to watch with friends?
35. What’s a classic movie you’ve never seen but want to?
36. Which movie world would you like to live in?
37. What’s a movie that completely blew your mind?
38. What’s a movie you loved as a kid and still love now?
39. Do you have a favorite movie soundtrack song?
40. What’s the first movie you remember seeing in a theater?
41. What movie do you think deserved an Oscar but didn’t get one?
42. Which actor or actress do you think is really underrated?
43. What’s the longest movie you’ve ever watched?
44. What’s your favorite foreign film?
45. What movie do you wish you could experience again for the first time?
46. Have you ever dressed up as a movie character for Halloween or a party?
47. What’s a movie that you think had the perfect ending?
48. What’s the funniest movie you’ve ever seen?
49. What movie scared you so much you had to sleep with the lights on?
50. Do you like watching behind-the-scenes or making-of videos about movies?
51. Who’s your favorite animated movie character?
52. What’s your go-to feel-good movie?
53. What’s a movie that taught you something new?

Questions To Ask About Travel And Adventure

1. What’s the coolest place you’ve ever been to?
2. Where’s your dream travel destination?
3. Have you ever traveled alone?
4. What’s the most adventurous thing you’ve ever done?
5. Do you prefer the beach or the mountains?
6. Have you ever gone camping? How was it?
7. What’s the longest flight you’ve ever been on?
8. Do you like road trips?
9. Have you ever traveled out of your country?
10. What’s the weirdest food you’ve tried while traveling?
11. Do you collect souvenirs when you travel?
12. What’s a place you’d never want to visit?
13. What’s your favorite travel memory?
14. Do you prefer hotels, hostels, or Airbnbs?
15. What’s the most beautiful place you’ve ever seen?
16. Have you ever been on a cruise?
17. What’s the most interesting cultural experience you’ve had?
18. What’s the next place on your travel bucket list?
19. Do you like visiting museums when you travel?
20. Have you ever gotten really lost while traveling?
21. Do you like flying, or does it make you nervous?
22. Have you ever traveled for a festival or event?
23. What’s the best travel tip you’ve ever received?
24. What’s a travel mistake you’ve made that you learned from?
25. Have you ever volunteered while traveling?
26. What’s the most exotic animal you’ve seen while traveling?
27. What’s your must-have travel item?
28. Do you prefer traveling with friends or family?
29. How do you entertain yourself on long journeys?
30. What’s the most spontaneous trip you’ve ever taken?

Questions To Ask About Hobbies And Interests

1. What’s a hobby you wish you had more time for?
2. Do you have any hidden talents?
3. What hobby do you love to get into but haven’t yet?
4. What’s the most recent hobby you picked up?
5. Do you play any sports?
6. Are you into video games?
7. Do you like to cook or bake?
8. What’s your favorite book?
9. What’s a hobby that relaxes you?
10. Do you do any creative writing?
11. Are you into photography?
12. Do you like to draw or paint?
13. What’s something you love to do outdoors?
14. Are you into gardening?
15. Do you have any favorite podcasts?
16. Do you play a musical instrument?
17. What’s your favorite board game or card game?
18. Do you enjoy puzzles or brainteasers?
19. Do you collect anything?
20. Are you into fashion?
21. Do you enjoy hiking or nature walks?
22. What’s a movie or show you can’t get enough of?
23. Do you enjoy DIY projects?
24. What’s your favorite YouTube channel?
25. Are you into astrology?
26. Do you like to dance?
27. Do you enjoy swimming?
28. Do you do any crafting like knitting or scrapbooking?
29. What’s your go-to workout?
30. Do you enjoy watching or playing any esports?
31. What’s the coolest thing you’ve ever built or made?
32. Do you enjoy any water sports like surfing or kayaking?
33. Do you like to go fishing or hunting?
34. Are you into any extreme sports like skateboarding or mountain biking?
35. Have you ever tried a hobby and realized it wasn’t for you?
36. Do you like watching documentaries?
37. What’s the last thing you binge-watched?
38. Are you into any specific types of art, like sculpture or digital art?
39. Have you ever tried geocaching?
40. What’s your favorite type of dance?
41. Do you like going to live sports events?
42. What’s the most challenging hobby you’ve ever taken up?
43. Have you ever tried acting or been in a play?
44. Do you enjoy singing, even if it’s just in the shower?
45. What’s a hobby that you think is really underrated?
46. Do you enjoy any winter sports like skiing or snowboarding?
47. What’s your favorite animal to see at the zoo or aquarium?
48. Are you into astronomy or stargazing?
49. What’s a hobby you used to love but don’t have time for now?
50. Do you enjoy learning about history or visiting historical places?

Questions To Ask About School

1. What’s your favorite subject? Why?
2. Do you have a favorite teacher? Who and why?
3. What was your most embarrassing school moment?
4. What’s the hardest class you’ve ever taken?
5. Do you like group projects? Why or why not?
6. Have you ever cheated on a test?
7. What’s your favorite school lunch?
8. What clubs or sports do you do at school?
9. What’s your least favorite subject? Why?
10. What’s the best grade you’ve ever gotten?
11. Have you ever had a crush on a teacher?
12. What’s the most boring class you have?
13. Have you ever gotten in trouble at school? What happened?
14. Do you like doing homework?
15. Have you ever been the new kid at school?
16. How do you usually get to school?
17. What’s the coolest project you’ve ever worked on?
18. Do you have a study buddy or a homework group?
19. Have you ever skipped school? Why?
20. What’s your favorite part of the school year?
21. Do you ever feel pressure to get good grades?
22. Do you have a rival at school?
23. What’s your go-to school outfit?
24. Have you ever been bullied? How did you handle it?
25. How do you deal with stress from school?
26. What’s the weirdest school rule you have?
27. What’s the most interesting thing you’ve learned this year?
28. Do you like your school’s mascot?
29. Have you ever won any school awards?
30. What are your plans after high school?
31. Have you ever pulled an all-nighter studying?
32. Do you have a favorite spot in the school library?
33. What’s the weirdest elective or optional class you’ve taken?
34. Did you ever have a teacher who changed your life?
35. Do you participate in school spirit days or events?
36. Have you ever had to retake a class?
37. What was the first club or team you joined in school?
38. Do you have a go-to snack for long school days?
39. Have you ever been part of a school play or musical?
40. What’s the most useless thing you’ve had to learn for school?
41. Have you ever failed a subject? How did you deal with it?
42. Did you ever have an embarrassing nickname at school?
43. What’s your strategy for taking notes in class?
44. Do you like taking online classes?
45. Do you have a best friend at school who you don’t see outside of school?
46. Have you ever gotten a grade you didn’t agree with?
47. What do you think about school uniforms?
48. Have you ever had to give a big presentation in class?
49. Do you prefer writing essays or solving math problems?
50. What’s one thing you wish you could change about your school?
51. What’s the most creative project you’ve done for school?
52. Have you ever had a substitute teacher who was really cool or really weird?
53. What’s your go-to study music?
54. Do you have a lucky pen or pencil for exams?
55. What’s the best field trip you’ve ever gone on?
56. How do you deal with difficult classmates?
57. Do you have any teachers who are also on social media?
58. Do you prefer morning or afternoon classes?
59. Have you ever been part of a student organization or student government?
60. How do you stay organized with your schoolwork?
61. Have you ever helped plan a school event?
62. What’s your biggest school-related fear?
63. Do you eat breakfast before going to school?
64. How do you usually spend your lunch break?
65. What’s the most recent book you’ve had to read for school?
66. Have you ever been to a school dance?
67. Do you prefer textbooks or online resources?
68. Have you ever won a school raffle or contest?
69. What’s the most challenging part about balancing school and social life?
70. What would you change if you could be the principal for a day?

Questions To Ask About Future Dreams

1. What’s your dream job?
2. Where do you see yourself in 10 years?
3. What’s a big life goal you have?
4. If you could live anywhere in the world, where would it be?
5. What’s something you want to achieve by next year?
6. Do you plan on getting any pets in the future?
7. What’s something you want to learn how to do?
8. Do you want to get married someday? Why or why not?
9. What would you do if you won the lottery?
10. Would you ever consider starting your own business?
11. What’s a skill you want to master in the future?
12. What’s your dream vacation?
13. Do you want to go back to school for anything?
14. What’s a country you want to visit before you die?
15. What’s something you hope to change about yourself in the next few years?
16. Do you see yourself staying in your current town or city?
17. What cause or issue do you want to advocate for in the future?
18. Do you have any plans to write a book or create something big?
19. What kind of legacy do you want to leave?
20. Do you plan on having kids? How many?
21. What’s an adventure you want to go on?
22. Would you ever consider living in another country?
23. What’s a fear you want to overcome?
24. Do you have any retirement dreams?
25. What would your dream house look like?
26. Do you have a dream car?
27. What’s something you want to be remembered for?
28. What job would you never want to have, even if it paid well?

Questions To Ask About Family

1. What’s your favorite family tradition?
2. Who are you closest to in your family?
3. What’s the funniest family story you’ve heard?
4. Do you have any siblings? What’s it like with them?
5. What’s your favorite home-cooked meal?
6. Do you have any family secrets?
7. Have you ever gone on a big family trip?
8. What’s a typical family dinner like at your house?
9. What do you and your family do for the holidays?
10. Who’s the goofiest person in your family?
11. Do your parents have any weird rules?
12. What’s something your family taught you that you’ll never forget?
13. How do you all handle arguments?
14. Do you have any pets? What are they like?
15. What’s your family’s favorite game to play together?
16. What does your family think about your friends?
17. Are there any famous or super-talented people in your family?
18. Who’s the best cook in your family?
19. Do you have family movie nights? 
20. What do you usually watch?
21. What’s the most important thing your family has given you?
22. What’s the oldest family heirloom you guys have?
23. Is there a family business?
24. How do your parents feel about your grades?
25. What’s your family’s go-to snack?
26. Is your family religious?
27. What’s the most surprising thing you found out about your family?
28. Do you all live close to your extended family?
29. What’s your favorite childhood memory with your family?
30. How does your family celebrate birthdays?
31. Have you ever had to keep a secret from a family member?
32. Who’s the best storyteller in your family?
33. Does your family have any weird habits?
34. Have you ever had a big family reunion? What was it like?
35. Who in your family can you always rely on for good advice?
36. Do you have a family member in the military?
37. What are some of your family’s New Year’s resolutions or traditions?
38. How does your family celebrate big achievements?
39. Is there a family member who’s really into technology?
40. Does your family do any charity work or volunteering?
41. Do you have any cousins you’re really close to?
42. What’s the longest time you’ve been away from your family?
43. Have any of your family members lived in another country?
44. What’s a typical weekend like at your house?
45. How does your family feel about you having sleepovers?
46. Do you have a favorite aunt or uncle? Why are they your favorite?
47. What’s the youngest memory you have of being with your family?

Fun Questions To Ask At A Sleepover

1. If you could have any superpower, what would it be?
2. What’s the first thing you’d do if you were president?
3. What’s your go-to dance move?
4. If you could switch lives with any celebrity for a day, who would it be?
5. What’s your zombie apocalypse survival plan?
6. If you could be any animal, what would you be?
7. What’s the most useless talent you have?
8. What’s your spirit animal?
9. What’s your favorite meme or internet joke?
10. If you were a character in a movie, who would you be?
11. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
12. If you could time travel, where and when would you go?
13. What’s the weirdest food combo you love?
14. If you were a superhero, what would your name be?
15. What’s the last photo you took on your phone?
16. What’s a silly fear you have?
17. If you could be on any game show, which would you pick?
18. What’s your signature dance move?
19. Do you have any weird rituals or habits?
20. What’s your favorite joke?
21. If you could talk to animals, what would you ask them?
22. What have you always wondered but been too afraid to ask?
23. What’s the craziest dream you’ve ever had?
24. If you had to eat only one food for the rest of your life, what would it be?
25. What’s your most embarrassing moment?
26. If you had to be on a reality TV show, which would you choose?
27. What’s the most recent show you binge-watched and loved?
28. What’s the weirdest nickname you’ve ever had?
29. If you had a boat, what would you name it?
30. Do you believe in aliens? Why or why not?
31. What’s the most daring thing you’ve ever done?
32. What’s the weirdest thing you’ve ever Googled?
33. If you had to listen to one song for the rest of your life, what would it be?
34. What’s the funniest YouTube video you’ve ever seen?
35. If you had three wishes, what would you wish for? (No wishing for more wishes!)
36. What’s your favorite board game to play?
37. If you could invent a holiday, what would it be, and how would we celebrate it?
38. Who would you be if you could swap lives with a cartoon character?
39. If you could instantly become an expert in something, what would it be?

---

Frequently Asked Questions

---

Final Thoughts

Asking the right questions can turn a simple night into one filled with laughter, stories, and maybe even a few secrets. The key is to keep things light, be open to everyone’s responses, and make sure everyone feels included.

So, next time you’re at a sleepover, don’t worry about what to say. Just relax and let the conversation flow with these questions. Who knows? You might learn something new about your friends and make the night one to remember.