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175 Funny First Date Questions To Ask Guys & Girls

The first date can be stressful as you anticipate that first conversational lull when you suddenly have nothing to say.

The best advice is to be yourself, try to relax, and ask questions to which you genuinely want to know the answer.

To help you along, I’ve listed some funny first date questions to keep the conversation going. 

Funny First Date Questions

Funny First Date Questions
  1. Should toilet paper hang over or under?
  2. What was the weirdest thing you did as a child that you are embarrassed about now?
  3. Could someone determine who you are based only on your Spotify or Netflix accounts?
  4. Did you ever hear someone call you the wrong name and not want to correct them? If so, what did they call you?
  5. Do you have a word you have pronounced wrong your whole life?
  6. What movie are you most embarrassed to admit you like?
  7. Which is a better awkward conversation starter, the weather or the food?
  8. How would you escape this date without being rude if you felt the need to leave?
  9. Are there any embarrassing things you’re afraid of? Are you afraid of something that most others wouldn’t find frightening?
  10. What two pictures would you choose if your life were an “expectation vs. reality” meme?
  11. Do you talk to your pets? What do you say to them?
  12. What’s the best WiFi name you’ve ever seen?
  13. How much time do you spend on TikTok every day?
  14. In what inappropriate moments have you found yourself giggling when you really shouldn’t have? 
  15. When you were younger, what did you often get into trouble for?
  16. What was the dumbest thing you ever did when trying to impress someone?
  17. What was one of those things you believed for too long as a child?
  18. Can you remember the worst middle school fashion trend you tried out? What is it? 
  19. What was your worst school photo?
  20. Have you ever been the victim of a practical joke? Have you ever pulled one off successfully?
  21. What would be the first thing you would do if you could switch genders right now?
  22. Is there a song you unknowingly sang the wrong lyrics to for a long time?

Watch this experiment where two strangers ask 36 questions to see if they will fall in love:

Funny First Date Questions To Ask A Guy

Funny First Date Questions To Ask A Guy
  1. Have you ever drunk texted anybody you wish you shouldn’t have?
  2.  Do you think I look the same as my social media profile pic?
  3. Which hangover food is your favorite?
  4. What’s your best dad joke?
  5. Do your best impression of me based on what you know of me so far?
  6. What is the cringiest thing you have ever Googled?
  7. What commercial made you decide not to buy the product advertised?
  8. Have you ever not made it to the toilet on the drive home?
  9. Which cartoon character would you say you are most like?
  10. If you were a DJ, what would your name be?
  11. If you survive the apocalypse, what would be your post-apocalyptic job?
  12. If you had to choose one absolute rule that everyone must follow for a day, what would it be?
  13. What would you choose to be if you had to become an inanimate object for a year?
  14. Where is the strangest place you’ve ever peed or pooped?
  15. What game are/were you really good at?
  16. Who would you marry if you had the chance to marry any fictional character?
  17. Suppose you were sent to prison for doing something bad. What would you have done?
  18. When was the last time you peed in a pool?
  19. What actor would be the best choice to portray you in a movie about your life?
  20. When you are about to get into a fight, what song plays as your soundtrack?

You might also like to read Cute Names To Call Your Crush

Funny First Date Questions To Ask A Girl

Funny First Date Questions To Ask A Girl
  1. Have you ever sent a text or email to someone you were bitching about by accident?
  2. What’s the most useless talent you have?
  3. Are you as cool in real life as you appear on Facebook?
  4. How many selfies do you take to find the perfect selfie?
  5. What is the most outrageous thing you’ve ever worn to a dress-up party?
  6. Would you rather have no eyebrows or hair like a troll doll?
  7. In case you had to smell like a particular food for the rest of your life, what would you choose?
  8. Do you think you could survive in a zombie apocalypse?
  9. Have you ever been so in love with a celebrity that you cried when they got a girlfriend?
  10. What are your thoughts on pineapple on pizza?
  11. Why did Cinderella’s shoe fall off if it fit well?
  12. Why did Mickey go into outer space?
  13. What would you prefer: permanently looking like a fish or permanently smelling like a fish?
  14. What is the funniest pick-up line that has been used on you?
  15. Is there one show, movie, or book you’re embarrassed to admit you enjoy?
  16. If you were unable to speak and could only communicate with an animal sound, which animal would you choose?
  17. Which celebrity couple would you consider relationship goals?
  18. What’s the most annoying habit an ex had? 

Funny Deep Questions To Ask 

Funny Deep Questions To Ask 
  1. What’s your most embarrassing date story?
  2. Are you more of a right-brain or left-brain person?
  3. Do you know what your love language is?
  4. If you found yourself suddenly transformed into a man/woman, what would you do?
  5. What is your worst first date experience?
  6. What are three words your mom would use to describe you?
  7. Do you think everyone has that ‘one’ person or soul mate they’re meant to be with?
  8. If you only had 48 hours left to live, what would you want to do in those last few hours?
  9. Tell me two truths and a lie, and I’ll try to guess which is the lie.
  10. What hobbies would you like to pursue if you had the time and money?
  11. Do you speak any other languages?
  12. Do you consider yourself a morning person or a night owl?
  13. Tell me the craziest thing on your bucket list.
  14. What’s the worst outdoor date you’ve been on? 

Funny Questions To Make You Think

Funny Questions To Make You Think
  1. Which bread do you think would fly the furthest – a naan tossed like a Frisby or a baguette thrown like a javelin?
  2. Which would you prefer: a horrible short-term memory or a terrible long-term memory?
  3. If you were arrested and no explanation was given, what would your friends and family suppose you had done?
  4. What mildly annoying curse would you like to throw at people?
  5. What color will the Smurf turn when you choke it?
  6. Which fictional location would you like to visit the most?
  7. Can eyebrows be considered facial hair?
  8. If you were a dog, what breed would you want to be?
  9. Would you rather be constantly itchy or constantly sticky?
  10. When you know the batteries on your remote control are dead, why do you press harder on the buttons?
  11. What sport would be the funniest if it had a mandatory amount of alcohol?
  12. Which would you rather do: Say all your words backward or communicate through charades for a week?
  13. Why are hemorrhoids called hemorrhoids instead of asteroids? 
  14. Coconut oil comes from coconut, so where does baby oil come from?
  15. What do you think your dog thinks of you?
  16. Why doesn’t glue stick on the inside of its container?
  17. Why is it that round pizzas come in square boxes?
  18. Why does ketchup not taste good on potatoes, but it does on French fries?
  19. If a turtle does not have a shell, is he naked or homeless?
  20. If the Energizer Bunny attacks someone, is it charged with battery?
  21. Which would you rather fight, a Ninja or a Navy Seal? 

Funny Questions To Ask In Online Dating

Funny Questions To Ask In Online Dating
  1. Are you embarrassed to be on a dating app?
  2. Are you looking for someone who can kill spiders for you?
  3. Do you like pineapple on your pizza?
  4. What is the most embarrassing fashion mistake you have ever committed?
  5. How do you react when people sing “happy birthday” to you in a restaurant?
  6. Which is the corniest one-liner you’ve ever received on this dating app?
  7. Have you ever laughed so hard that you spilled food or water on someone?
  8. My dog looks just like yours. Do you think they’re related (insert picture of dog)?
  9. Would you spend a night in a haunted house if you could?
  10. The only condiment you can use for the rest of your life is ketchup, ranch, or hot sauce. What will you choose?
  11. Have you ever accidentally liked an old picture or a comment on your crush’s profile while browsing their profile?
  12. Who do you think you might have been in a past life?
  13. When you were a kid, what was the first poster you hung on your wall?
  14. What would be your line if you wanted to pick up a guy in a bar?
  15. Have you ever made a TikTok dance?
  16. Would you rather have a roommate who snores or farts?
  17. Which would you choose – date the most irritating person you have ever met for a month, or not date at all for a year?
  18. If you got stuck on an elevator, who would be the worst person to be with?
  19. What would peanut butter be called if it wasn’t called peanut butter?
  20. What would your stage name be if you became famous?
  21.  Have you ever been in a food fight? 

Funny Icebreaker Questions For Dating

Funny Icebreaker Questions For Dating
  1. What would you most likely be doing if someone took a candid photo of you?
  2. What would the police find you doing if they suddenly broke into your house in the middle of the day?
  3. How long have you ever binge-watched Netflix?
  4. Do you ever text random people for fun?
  5. Where would you want to go if we could travel anywhere right now?
  6. What animal would you rather trade lives for a day: your cat or your dog?
  7. Do you sort your laundry by color or just mix it all together?
  8. If you had to choose one song to perform at karaoke, what would you pick?
  9. What TV show/movie character were you scared of when you were a child?
  10. Do you have a commercial song that always gets stuck in your head?
  11. What superpower would you like to have?
  12. What emoji do you have a bad relationship with?
  13. If you had your own talk show, what would it be called?
  14. What’s the funniest dream you’ve ever had?
  15. What is your favorite pick-up line? 

Funny First Date Conversation Starters

Funny First Date Conversation Starters
  1. Which is the worst excuse you’ve ever used to call in sick to work?
  2. What is the funniest injury you have ever been hospitalized with?
  3. Name one food that you would never try even if someone offered you a hundred dollars to try it.
  4. If you could go back in time, what would you advise yourself as a teenager?
  5. As an elementary school student, were you awkward or cool?
  6. What is your favorite random food combination?
  7. What are your pet peeves?
  8. What is cleaner: your car or your bedroom?
  9. What would you rather be – a fly on the wall of the White House for an entire day or a gardener at the White House for a whole week?
  10. Which food would you eat if you could only eat one for the rest of your life?
  11. Do you think I look like my profile picture on social media?
  12. Would you still work if you won $10 million in the lottery?
  13. Of all the stale jokes out there, what’s the worst joke you’ve ever heard?
  14. If you have an itch in your nose, butt, and eye, which one do you scratch first?
  15. Zombie invasion. Who are the three people on your defense team?
  16. What three apps would you keep on your smartphone if you had to choose only three?
  17. If you could have one thing in unlimited supply for the rest of your life, what would it be? 

Terrible Funny Things To Say On First Date

Terrible Funny Things To Say On First Date

These pick-up lines won’t work, so don’t even try them. However, your date may ask you about the worst pick-up line you’ve ever heard, so here are some of the most terrible yet funny things you could say.

  1. You’re So Beautiful; I Just Forgot My Pick-Up Line.
  2. How did I get into organ donation so early in life? My heart is already yours.
  3. Have you tied my shoelaces together? Because you’ve got me tripping over you. 
  4. I’m trying to look cool, so please stop making me so interested in you
  5. Got Band-Aid? I scraped my knee falling for you.
  6. You have something beautiful on your face. Oh wait, that’s just you.
  7. You’re making my knees weak for falling for you.
  8. Was it painful? When you fell out of heaven?
  9. Are you lost? Heaven is far from here.
  10. Are You Religious? You’ve been the answer to all of my prayers.
  11. Now sit down and take a break. You’ve been running through my mind all day long.
  12. Millions of dollars are wasted on research when the true cause of global warming is right in front of me.
  13. I don’t need a camera to make me smile, just make me look at you!
  14. Have you ever been arrested before? It’s illegal for you to look that good. 

Here are some more super terrible yet funny questions men want to ask but shouldn’t:

Related First Date Questions

What questions should you avoid on a first date?

  1. Why did you and your ex break up?
  2. How’s your relationship with your parents?
  3. How many people have you slept with?
  4. Do you want to get married?
  5. How much money do you make? 
  6. What religion do you believe in?
  7. What do you think is the most important political issue at the moment?
  8. Do you always wear this much makeup? 

What are good topics of conversation for a first date?

  1.  Talk About Where You’re From
  2. Talk about your childhood
  3. Talk about your ambitions
  4. Talk about each other’s typical day
  5. Say something about your favorite movies, TV shows, and books
  6. Open up about your hobbies
  7. Chat about your favorite music
  8. Start a conversation about travel
  9. Talk About Food 

Should you kiss on the first date?

 Intimacy is something that varies significantly from person to person, depending on how at ease you are expressing it. People express physical intimacy at a different pace, and sometimes it might be appropriate to do so in certain circumstances. Kissing someone you’re just getting to know depends on how your date feels about it and whether you feel comfortable doing so. If you both feel a connection then go for it!