25 Witty Icebreaker Questions for a Memorable First Date

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First dates are a rollercoaster ride of emotions, anxiety, and the occasional panic-induced sweat. However, they don’t have to be. You can get some little practice from learning some icebreaker questions to help you soothe into the date.

Whether you are a pro at love or a rookie, you can still master the art of first-date conversation with icebreaker questions. What better way to make your date comfortable than with a simple kickstarter?

These questions are not for the faint-hearted, so brace yourself for weird answers and giggles.

1. If you could be any superhero, who would you choose to be and why?

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Nothing screams character like their choice of spandex-wearing superhero. Will your date go for the classic superheroes like Batman and Superman? Or do they prefer dark superheroes like Deadpool and Wolverine? All in all, you are in for a giggle, especially when they start explaining why.

2. What would they be if you were stuck on a desert island and could only bring one to three things?

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Here you go if you want an icebreaker question to reveal your date’s priorities. Will they go for survival necessities or unusual things like a power bank, pizza, and satellite?

3. What’s the most embarrassing thing that happened to you?

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You should skip this question if you easily cringe from secondhand embarrassment. Besides breaking the ice, this question will help you start with hilarious inside jokes. Expect anything, from wardrobe malfunctions, cringing, snorting laughs to a possible tear. 

4. What weird food combination have you tried?

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Everyone has a guilty pleasure, and it may be weird for some people. The culinary adventures of your date will show you how daring they are when it comes to food. Additionally, this question will help you score a second food-tasting date. Wink! Wink!

5. If you could swap lives with a fictional character, who would you want to be and why?

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You may hear a lot of Disney princess stories and Harry Potter characters. Everyone has a fictional alter ego that comes alive whenever they watch a movie or TV show. Through this question, you will know if your TV culture preferences match in case the next date night is a movie night.

6. What’s your favorite Karaoke song, and can I get a short sample?

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Karaoke screams confidence and vocal ability. You will get to know the music taste of your date, and it also gives you a chance to join in and duet, making the date memorable. Just pray they don’t choose a Micheal Jackson song because the moonwalk may be in the preview.

7. Would you rather fight a hundred duck-sized horses or one horse-sized duck?

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The allure of hypothetical questions will have you battling your mind for hours. Any hypothetical question you decide to ask will show you how strategic and competitive your date can get.

8. Who would you choose if you could have dinner with a historical person?

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There are endless possibilities. More often than not, you cannot guess what your date will say. You will get to enjoy a lengthy discussion of philosophy and history. Don’t make it boring by forcing them to choose from an era you like.

9. What skill would you like to master instantly and why?

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The answers to this question always get weird. You can learn what your date likes to do to pass the time, their aspirations, dreams, and hidden talents. You might find a potential client or business partner with the answer to this question.

10. If you could watch one movie or TV show for your entire life, which would it be?

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Everyone has that one movie or TV show they can watch on repeat for eternity. You will learn the movie and TV show tastes of your date. You may also debate the best actor if you share the same taste.

11. What conspiracy theory do you secretly believe in?

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Conspiracy theories are entertaining. Get ready to hear crazy stories, from octopi taking over the world to werewolves roaming the streets during a full moon. Conspiracy theories help you see how imaginative your date can get. Some of them make sense, while others may not.

12. What’s the most embarrassing thing you’ve ever laughed at publicly?

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Inappropriate laughter gives you a glimpse of how much dark humor your date can table. We all have had a moment where we’ve laughed in an unacceptable situation, from horror movies to sad funerals. Not only will this question break the ice, but it will set the stage for hilarious confessions.

13. What superpower would you wish to have and why?

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Invisibility, flying, underwater breath control, the answers will have you glued to the edge of your seat. Expect debates, humor, and a possible fight on who would win a battle if you went toe-to-toe.

14. What’s your go-to comfort food?

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Everyone has that one email that soothes their soul and tummy. The first meal that pops into your mind when you think about eating. If you like cooking, use this as a gate pass to ask for another date.

15. What’s at the top of your bucket list?

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If you like spontaneity, this might be your cue to open your notepad and table down some notes. You can use your date’s bucket list to plan your next date. Helping someone tick their boxes will make you more memorable.

16. You are hosting a dinner party and can invite three people, dead or alive; who would you bring?

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Nothing says ‘fun dinner’ like having a good conversation with Princess Diana and Rihanna. Get ready for some weird guest combinations and a possible snorting laugh.

17. What did you aspire to be when you were a child?

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Let’s rewind the clock and listen to adorable baby stories. The stories get even better if there are baby pictures to show as you tell your story. You will hear some adorable and hectic aspirations like being a superhero by night and an astronaut by day.

18. If you could learn a language overnight, what would it be and why?

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Some people want to learn a language to travel or advance their careers. Others just want to understand song lyrics, and that’s okay. You can use this as a stepping stone to becoming Duolingo partners.

19. If you could have any job in the world for a day, what would it be and why?

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Be prepared for a wholesome debate on who gets to work at the Daily Planet right across from Superman or at Willy Wonker’s Factory. The career possibilities are a lot. Asking this question will give you a glimpse of what career your date would have pursued if it was up to them.

20. What’s your favorite dad joke?

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Who doesn’t love a good, funny dad joke? Whether you are cringing or snorting with laughter, we can all agree that dad jokes hit the spot. Don’t be afraid to show off your goofy side.

21. If you could invent a holiday, what would it be?

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You can go the extra mile in this question to learn how your date would want the holiday to be celebrated. Allow your date’s imagination to run wild, and you will not be disappointed. The answer to this question might get extremely funny or weird.

22. What is your spirit animal, and why?

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A spirit animal is an animal that embodies someone’s character. An animal you feel connected to because of its character. You could choose to be a loyal dog or a majestic eagle. Figure out which animal resonates with your character and enjoy your self-discovery.

23. What’s a ridiculous rumor you’ve heard about yourself?

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From workplace issues to school gossip, anything goes wrong when answering this question. Prepare to hear the most outrageous false facts about your date and ensure they set the record straight after having a good laugh.

24. What’s the most embarrassing thing you’ve ever googled?

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Google knows everything. Let’s face it: we have all googled something strange on the internet, whether it’s what your crush’s statement meant or the lyrics to an anime song. 

25. What’s the most embarrassing thing that ever happened to you on a date?

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Dating disasters are more common than you think. Maybe you’ve had a similarly embarrassing moment with your date. It could be getting food stuck in your teeth, accidentally knocking off a glass of wine from a table, or bumping into a waiter.

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