110 Freaky & Flirty “21 Questions” Ideas to Ask Your Crush (2024)

Co-authored byBailey ChoReviewed byJohn Keegan

Last Updated: May 21, 2024Fact Checked

Fun & Flirty Questions to Ask Your Crush

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1. Ask spooky questions to break the ice and bond with someone. Trying to start a silly conversation that sends a chill down their spine? Ask someone about the supernatural, scary movies, or eerie hypothetical situations. It’s the perfect way to get to know them better and prompt a lively discussion!

   • Do you believe in aliens?
   • Do you have any phobias?
   • Have you ever used an ouija board?
   • Do you have any weird superstitions?
   • Do you believe in any conspiracy theories?
   • Have you ever experienced sleep paralysis?
   • What’s the worst nightmare you’ve ever had?
   • What do you want etched on your tombstone?
   • Would you rather be a werewolf or a vampire?
   • Would you rather swim with sharks or jellyfish?
   • Have you ever had a supernatural experience?
   • Which horror movie still scares you till this day?
   • Would you ever spend the night in a haunted house?
   • Do you think you could survive a zombie apocalypse?
   • Would you rather be in a room full of spiders or snakes?
   • If you could direct a new horror movie, what would the plot be?
   • If you were trapped in a horror movie, which one would you choose?
   • Would you rather know the date of your death or the cause of your death?
   • Would you rather be the only survivor in a zombie apocalypse or when machines take over?
   • Which character would you be in a horror movie—the first to die, the last one standing, or the killer?

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1. Spice up game night by asking your crush a cute or flirty question. If you’re playing with your crush, use the game as an opportunity to see if they like you back. Find out their turn-ons, usual type, and everything in between—it’s the perfect way to gauge if you’d be a good match too!

   • What’s your toxic trait?
   • What’s your usual type?
   • What gives you the “ick”?
   • What’s your love language?
   • What song puts you in the mood?
   • Do you prefer kissing or cuddling?
   • When did you have your first kiss?
   • Do you think you’re a good kisser?
   • Do you believe in love at first sight?
   • What’s your biggest guilty pleasure?
   • What’s your favorite thing about me?
   • What’s your idea of the perfect date?
   • What was your first impression of me?
   • Have you ever had a dream about me?
   • What are your green flags in a relationship?
   • What’s the most attractive physical feature?
   • Who’s the hottest person in our friend group?
   • What’s the best pick-up line you’ve ever used?
   • Would you rather be single or in a relationship?
   • Have you ever sent a dirty text to the wrong person?
   • What’s the funniest excuse you’ve used to get out of a date?
   • What’s the craziest thing you’ve ever done to get someone’s attention?

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1. Crank up the heat with these spicy and suggestive questions. If you’ve known the other players for a while and they’re pretty open about their sex lives, up the stakes with some risqué questions. Just make sure that everyone is comfortable while you’re playing, and throw out some tamer questions throughout the game so things don’t get too spicy.

   • What’s your favorite position?
   • Who’s your celebrity hall pass?
   • Do you prefer giving or receiving?
   • How often do you think about sex?
   • Fast and fiery, or slow and sensual?
   • What’s your biggest sexual fantasy?
   • Have you ever gone skinny dipping?
   • What’s your favorite part of my body?
   • Have you ever been caught in action?
   • Have you ever been turned on at work?
   • What’s your favorite place to be kissed?
   • Do you have any weird kinks or fetishes?
   • Do you prefer being on top or on bottom?
   • What’s the craziest place you’ve had sex?
   • Do you prefer loud or silent people in bed?
   • Do you prefer morning sex or evening sex?
   • What’s your hottest memory of the two of us?
   • What’s your most awkward sexual experience?
   • What clothing do you think I look the sexiest in?
   • What’s the first thing you told your friends about me?
   • Did you stalk me on social media before we started dating?
   • What’s the first thing that comes to mind when you think of me?

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1. Throw out funny and playful questions to lighten the mood. If you want to have fun with your friends, introduce a quirky and thought-provoking question to catch everyone off guard. Asking a “what if” or “would you rather” style question is a great way to elevate the game, but feel free to ask something silly or random to make everyone laugh.

   • What’s your favorite scent?
   • Do you have any hidden talents?
   • What’s your biggest irrational fear?
   • What’s the theme song of your life?
   • Are you a night owl or an early bird?
   • What’s the #1 thing on your bucket list?
   • Did you go through any phases as a kid?
   • What’s your unpopular opinion or hot take?
   • Do you prefer watching movies or TV shows?
   • Would you rather explore space or the deep sea?
   • If you were invisible for a day, what would you do?
   • What’s the funniest thing you believed in as a child?
   • If you could have any superpower, what would it be?
   • If you could fight any historical figure, who would it be?
   • If you could time travel, which decade are you going to?
   • If you could change your name, what would you choose?
   • What’s an embarrassing song or band you secretly love?
   • If you could live in any fictional world, where would you go?
   • Would you rather talk like Yoda or breathe like Darth Vader?
   • What’s one inanimate object you would remove from existence?
   • If you were given the death penalty, what would your last meal be?
   • If you could create your dream band with 5 artists, dead or alive, who would be in it?

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1. Ask about their past and personality to delve into a deeper conversation. Ready to deepen your connection with everyone in the room? Touch on meaningful topics that move beyond the surface, such as their dreams, fears, beliefs, and childhood. If you’re worried about bringing up personal questions, preface by saying it’s okay not to respond if anyone feels uncomfortable.^[1]

   • Are you religious?
   • Who’s your role model?
   • What’s your top goal in life?
   • What keeps you up at night?
   • When’s the last time you cried?
   • What are you most grateful for?
   • What are you the most proud of?
   • What’s your biggest regret in life?
   • Do you believe in fate or free will?
   • Is the glass half-full or half-empty?
   • What’s something you can work on?
   • What was your dream job as a child?
   • Where do you see yourself in 10 years?
   • What’s your favorite childhood memory?
   • Do you think money can buy happiness?
   • How have you changed in the past year?
   • What’s something you’re insecure about?
   • What are 3 things you love about yourself?
   • What role do you play in your friend group?
   • Do you think physical or emotional pain is worse?
   • What’s the best piece of advice you’ve ever received?
   • What’s the biggest misconception people have about you?
   • If you could solve one problem in the world, what would it be?
   • If your life was a book, what’s the title of the chapter you’re in now?

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1. Take turns asking questions and letting each person answer them aloud. While you only need 2 people to play 21 Questions, it’s more fun if you have a large group of 4 or more players. The goal of the game is for everyone to answer 21 questions, so choose someone to ask the first question and wait for everyone to respond. Once everyone has answered, move onto the next person.^[2]

   • Before playing, determine questions that are “off-limits,” such as ones about sex and intimacy, past relationships, or family upbringing.
   • Be mindful of your questions and set rules that allow each person to skip a turn. If you think your question might be too serious or make someone feel uncomfortable, it’s best to save it for another occasion, such as a one-on-one conversation with the other person.

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