150 Funny Questions to Ask Your Boyfriend

Silly Hypotheticals to Get Him Talking

These start small and get weird fast. Watch how long he actually thinks before answering.

1. If you woke up as a golden retriever for a day, whose shoes would you chew first?
2. Would you rather have spaghetti for hair or sweat maple syrup?
3. If our fridge could talk, what embarrassing thing would it say about you?
4. What would your wrestling name and entrance song be?
5. If you had to replace your laugh with an animal sound, which one are you picking?
6. Would you rather fight one horse-sized duck or a hundred duck-sized horses, and what's your strategy?
7. If you were a kitchen appliance, which one would you be and why?
8. Which cartoon villain do you secretly think had a point?
9. If a ghost moved into your apartment, what chore would you make it do?
10. Would you rather only whisper or only shout for the rest of the week?
11. If you could shrink one thing in the world to pocket size, what would it be?
12. What's the dumbest superpower you would still happily accept?
13. If your life had a laugh track, which moment this month would get the biggest laugh?
14. Would you rather narrate your life out loud or have a stranger narrate it?
15. If you were stuck in an elevator with a celebrity, who would annoy you most?
16. Which fast food mascot would you trust to babysit?
17. If pets could vote, who do you think they'd elect?
18. Would you survive a zombie movie past the first scene?
19. If you could rename every day of the week, what names are going on the calendar?
20. What would your ice cream flavor be called if they named one after you?
21. If you had to wear one costume every day for a year, what's the pick?
22. Which vegetable do you think would be the rudest if it could talk?
23. If you were a ghost, how would you haunt me?
24. What's the most useless invention you'd pitch on a shark tank show?

Questions About His Weird Habits

Every guy has quirks he thinks nobody notices. These let him own them.

1. What's something you do alone that you'd be mortified if I saw?
2. Do you talk to your car, and what do you usually say?
3. How do you really eat an Oreo when nobody is watching?
4. What song do you sing in the shower when you think I can't hear?
5. Which weird food combo do you swear by?
6. What's the strangest thing in your nightstand drawer right now?
7. Do you have a secret nickname for any of our neighbors?
8. What's your go-to dance move when a good song comes on in the kitchen?
9. How many unread texts are sitting on your phone this second?
10. Which of your habits do you think drives me the most bonkers?
11. What do you actually do in the bathroom for twenty minutes?
12. Have you ever practiced a conversation in the mirror?
13. What's one thing you refuse to throw away even though it's useless?
14. Do you rehearse your coffee order before you get to the counter?
15. Have you ever pretended to know a song at a party?
16. Which chore do you pretend you don't know how to do?
17. What's the oddest thing you've ever googled at two in the morning?
18. Do you ever wave back at someone who wasn't waving at you?
19. Which snack have you hidden from me before?
20. What's your weirdest superstition that you actually follow?
21. How long could you go without checking sports scores or your phone?
22. What's a word you always mispronounce on purpose?
23. Which sock goes on first, and do you have a reason?

Funny Questions About Us

Inside jokes are built from questions like these. Keep your phone handy for the answers.

1. What was your honest first thought when you saw me?
2. Who do you think would win if we played a board game with no rules?
3. If we starred in a reality show, what would it be called?
4. Which one of us would get eliminated first on a cooking competition?
5. What's my most annoying habit that you secretly find cute?
6. Who is the bigger baby when we're sick?
7. If our relationship was a sitcom, who would be the comic relief?
8. What's the most ridiculous thing we've ever argued about?
9. Which of my outfits do you quietly hope I throw away?
10. Who would our pets say is their favorite?
11. What's a moment from one of our dates that still makes you laugh?
12. If we swapped bodies for a day, what's the first thing you'd do?
13. Which of my friends would you trade me for in a trivia night?
14. Who takes longer to get ready, really?
15. Which of my family members do you do the best impression of?
16. What's the worst gift you've pretended to like from me?
17. Who is more likely to get us lost on a road trip?
18. If we opened a restaurant together, what would go wrong first?
19. What's something I say that you've started saying too?
20. Which of my snoring sounds is your favorite?
21. Who would survive longer on a deserted island, you or me?
22. What would our theme song be if we walked into every room together?
23. Who hogs the blanket, and are you ready to admit it?

Embarrassing Stories He Might Not Want to Tell

Go easy on these. The goal is to laugh with him, not at him.

1. What's the most embarrassing thing that happened to you in middle school?
2. Have you ever walked into a glass door in public?
3. What was your worst haircut and who talked you into it?
4. Did you ever get caught lip syncing badly?
5. What's the worst pickup line you've actually used?
6. Have you ever sent a text to the wrong person?
7. What's the most awkward thing you've said to a boss?
8. Did you have a cringey screen name as a teen?
9. What's the silliest reason you've ever gotten in trouble?
10. Have you ever tripped on stage or in front of a crowd?
11. What's the most embarrassing thing your parents have told me about you?
12. Did you ever wear a trend you now deeply regret?
13. What's the worst thing you've ever cooked for someone?
14. Have you ever fallen asleep somewhere really inappropriate?
15. What's a lie you told as a kid that got way out of hand?
16. Have you ever waved at a stranger thinking it was a friend?
17. Which old photo of you should never see daylight?
18. What's the goofiest thing you did to impress a crush?
19. Have you ever laughed at a completely wrong moment?
20. What's the worst karaoke song you've ever attempted?

Would You Rather for Boyfriends

Quick picks that make great car ride or waiting-in-line questions.

1. Would you rather give up pizza forever or give up tacos forever?
2. Would you rather live in a treehouse or a houseboat?
3. Would you rather always have a pebble in your shoe or a tag scratching your neck?
4. Would you rather be famous for a terrible song or unknown for a great one?
5. Would you rather lose your eyebrows or your ability to whistle?
6. Would you rather wear socks with sandals every day or flip-flops in the snow?
7. Would you rather have a pet dinosaur or a pet dragon the size of a cat?
8. Would you rather always be ten minutes late or an hour early?
9. Would you rather speak every language or talk to animals?
10. Would you rather eat cereal with orange juice or pizza with ketchup?
11. Would you rather never use a phone again or never watch TV again?
12. Would you rather live one day as your dad or one day as your boss?
13. Would you rather have your search history read out loud or your texts?
14. Would you rather win a lifetime of free burgers or free video games?
15. Would you rather relive your best birthday or skip your worst one?
16. Would you rather be a famous chef or a famous athlete?
17. Would you rather have my morning mood or my hangry mood?

Random Questions for Late Night Laughs

Save these for when you're both tired, giggly, and not ready to sleep.

1. What do you think cats are thinking when they stare at the wall?
2. Why do you think we park on driveways and drive on parkways?
3. How many chickens do you think you could fight at once?
4. Which conspiracy theory would you believe if you were half asleep?
5. What's the best name for a pet goldfish you've ever heard?
6. How do you think penguins would describe humans?
7. Who invented the idea that breakfast has to be sweet?
8. What's the worst possible thing to hear during a surgery?
9. How would you explain the internet to a pirate?
10. Which emoji best describes your personality today?
11. What do you think aliens would find weirdest about us?
12. Who would win in an arm wrestle, a kangaroo or a gorilla?
13. How long could you survive on only gas station snacks?
14. What would you rename the moon if you got the chance?
15. Which dinosaur do you think would make the worst roommate?
16. What's the most suspicious thing about pigeons?
17. How many bananas tall do you think you are?
18. What's a job that probably exists that sounds totally made up?
19. Which sound effect would you want every time you sit down?
20. If socks disappear in the dryer, where do you think they end up?
21. What's the most overrated holiday and why?
22. Which fruit would make the funniest hat?
23. How would you describe me to a squirrel?
24. What's the worst flavor of chips you can imagine?
25. Which song would you pick as the official anthem of naps?
26. What would you teach a parrot to say to annoy guests?
27. Who in your family would be the worst at hide and seek?
28. What's the strangest dream you can still remember?
29. Which nursery rhyme makes the least sense to you?
30. If you could only eat foods of one color, which color wins?
31. What's the funniest word in the English language?
32. Which tiny animal would be scariest if it were giant?
33. How would a toddler describe your job?
34. What's the best excuse for being late you've ever heard?
35. Which cereal mascot do you think has the most drama?
36. What should the national sport be if it had to involve cheese?
37. Who would you call first if you got arrested for something silly?
38. What sound do you think a giraffe makes?
39. Which store would be the best place to hide during a sleepover?
40. What would be the worst thing to yell at a library?
41. Which kids board game would you cheat at to beat me?
42. What would a raccoon steal first from our kitchen?
43. Which celebrity do you think smells like pancakes?

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