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Do you want to know if a girl is just as weird as you? Tap into her weird side by asking her unusual and random questions! To help you spark an interesting conversation, we’ve compiled a list of 80 creative questions that are sure to keep her on her toes. These questions will let her show off her weirdness and will tell you more about her interests, values, and past.

Things You Should Know

  • Start a funny conversation with a random question, a game of “would you rather,” or a silly hypothetical situation.
  • Ask about her embarrassing moments, her funny childhood memories, and supernatural experiences.
  • Quiz her on her favorite foods, celebrities, movies, and items she collects.
1

“What food would you choose to build a house out of?”

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  1. How creative and unusual her answers are will tell you whether your weirdness levels are compatible. Ask her why she chose her food and start a funny debate if you think a different food is better. [1]
    • “How many butterflies would it take to beat a lion?”
    • “What liquid would you want to come out of your sink besides water?”
    • “What would computers taste like if they were edible?”
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2

“If you were a type of flower, what would you be?”

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  1. Her answer can give you insight into her personality. If she wants to be a rose, she might be more traditional but have an edge to her. If she wants to be a sunflower, she’s probably cheerful and bubbly.
    • “If you were a mythical creature, what would you choose to be?”
    • “If you were a type of writing instrument, what would you be?”
    • “If you were a piece of furniture, what would you be?”
3

“Would you rather travel to another galaxy or to a parallel universe?”

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  1. Get creative with your options to keep the game fun. Ask her why she chose her answer and share what you would choose too. [2]
    • “Would you rather know what people are thinking when you touch them or be able to mind control people, but they know that you’re controlling them?”
    • “Would you rather turn green when you’re lying or break out into polka dots when you’re mad?”
    • “Would you rather swallow a fly every time you drink water or wake up with a worm in your bed everyday?”
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4

“You discovered a new species of animal. What does it look like? What do you call it?”

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  1. You can take the question a step further by asking her what the new species sounds like and where it lives. Her answer might tell you more about her favorite animal and the places she’d like to go. [3]
    • “You can make any animal in the world talk. Which animal do you grant this power to?”
    • “If you could give any non-flying animal the ability to fly, what would you choose?”
    • “If you could make any bug in the world as big as a bear, what would you choose?”
5

“If you were invisible for a day, what would you do?”

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  1. What she chooses to do can tell you about the kind of person she is. She might be a risk taker and steal money from a bank, or be sneaky and listen to conversations she shouldn’t be a part of. [4]
    • “What wouldn’t you be scared to do if no one was watching?”
    • “Would you shoplift from your favorite store if you knew you wouldn’t get caught?”
    • “What room in the world would you fly into if you could be a fly on the wall?”
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6

“You can trade lives with your favorite celebrity for a day. Who do you choose and what do you do?”

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  1. These questions can give you an idea of the people that she admires and the kinds of movies and shows she enjoys. If she chooses Tom Holland, she’s probably a superhero fan, or if she chooses Julia Roberts, she’s likely a romcom lover. [5]
    • “If you could get dinner with any public figure, dead or alive, who would you choose?”
    • “If you were an assistant to any celebrity, who would you choose?”
    • “If you could go on a date with a celebrity, who would you choose?”
7

“What weather condition would you permanently set the world to?”

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  1. Is she all sunshine and rainbows or does she prefer it when it’s dark and gloomy out? Her answer might reveal her outlook on life. [6]
    • “If you could only see the world in one color, what color would you choose?”
    • “You have to set the world to be permanently hot or cold. What do you choose?”
    • “If you had to change the color of grass and trees, what color would you choose?”
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8

“What’s the most uncomfortable situation you’ve been in?”

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  1. Laughing and sharing awkward stories builds trust between you and can help you grow closer. Tell her your embarrassing stories too so she doesn’t feel uncomfortable opening up. [7]
    • “What’s something that makes you cringe?”
    • “What’s the most unbelievable lie you’ve told?”
    • “What’s your most embarrassing moment?”
9

“What 3 things would you grab from your bedroom if your house was on fire?”

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  1. If she chooses her phone, gym bag, and hiking boots, you can tell she values her friends and the outdoors. Or, if she chooses her sketchbook, favorite book, and journal, she probably appreciates the arts and her alone time. [8]
    • “If you were stranded on an island, what 5 things would you bring to help you survive?”
    • “You are granted 3 wishes. What do you wish for?”
    • “What one item could you not live without?”
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10

“You find a time machine that takes you 1500 years into the past or 500 years into the future. Which option do you choose?”

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  1. This is a fun way to learn more about her personality and interests. If she says the future, she might love technology and new things. If she wants to go back to the past, she might be more of an old soul. [9]
    • “Where would you want to travel if you had an unlimited budget?”
    • “If you could travel into the past, how far back would you go and where would you like to be?”
    • “If you could choose where in the world you were born, what country or city would you choose?”
11

“What’s your favorite smell?”

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  1. It can be predictable to ask about her favorite food, color, and animal, so keep her on her toes and interested with these random questions. Keep the conversation going by asking why and telling her what your favorite is too! [10]
    • “What’s your favorite Halloween costume you’ve worn?”
    • “Who is your favorite cartoon character?”
    • “What’s your favorite type of french fry?”
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12

“What’s the weirdest conversation you’ve overheard?”

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  1. Maybe she overheard a dramatic break up or two friends thinking of crashing a wedding. You can ask her where she was when she heard the conversation to learn about places she’s traveled to and the unusual people she’s met. [11]
    • “What’s the most unusual interaction you’ve had with a stranger?”
    • “What’s the weirdest text you’ve ever received?”
    • “What’s the juiciest gossip you’ve heard about complete strangers?”
13

“Have you ever had a supernatural experience?”

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  1. You might be surprised to find that she secretly believes there’s monsters and ghosts lurking in the shadows. Be prepared to hear a spooky story that will raise the hairs on the back of your neck! [12]
    • “Do you believe in witches?”
    • “Have you ever played with an Ouija board? Did anything happen?”
    • “Are there any urban legends or conspiracies that you believe are true?”
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14

“What’s the weirdest gift you’ve ever received?”

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  1. What she says can tell you a lot about her hobbies and things she enjoys. She might have received a fossilized mosquito because she likes to collect bugs. [13]
    • “Is there anything you collect?”
    • “If you had all of the money in the world to collect one thing, what would you choose?”
    • “What’s the best gift you’ve ever received?”
15

“What’s the weirdest thing you’ve ever eaten?”

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  1. This can tell you if she’s an adventurous or picky eater. Ask her where she ate the food and whether she’d try it again! [14]
    • “What 2 foods do you think go well together that other people don’t?”
    • “If you could only eat one dessert for the rest of your life, what would it be?”
    • “If you could only eat foods that start with the same letter, what letter would you choose?”
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16

“What’s a movie you love, but everyone else seems to hate?”

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  1. She might say that she genuinely liked Cats , which can tell you that she’s a musical fan, a cat lover, or both! Be sure to share your answer so she can tease you too. [15]
    • “What’s your guilty pleasure movie or show?”
    • “What movie could you watch over and over?”
    • “What show, book, play, or podcast do you think should be made into a movie?”
17

“What unusual thing did you believe in as a kid?”

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  1. Maybe she thought swallowing a watermelon seed would make it grow in her stomach or that teachers lived at school. You can discover a lot about her upbringing, family, and memories that make her laugh by asking about her childhood. [16]
    • “What’s your funniest childhood memory?”
    • “What impressed you as a child that is normal to you now?”
    • “Who’s the weirdest person in your family?”
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18

“What’s a random fact that no one else knows about you?”

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  1. Chat about her skills and the obscure things about her that she doesn’t usually tell anyone. You might be surprised to learn that she can burp the “ABCs” or that she has 11 toes. [17]
    • “What’s a useless skill you have?”
    • “What’s a funny quirk or ability that you’re known for?”
    • “What’s something that you’re good at that you’ve never shown or told anyone about?”
19

“What is the healthiest and unhealthiest thing you do?”

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  1. You might be surprised to find out that she loves to run but stays up until 1 am every night watching reality TV. Don’t be ashamed to share your funny quirks with her too! [18]
    • “How many pillows do you sleep with?”
    • “What’s your weirdest habit?”
    • “What do you like to do when you’re stressed?”
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20

“What’s the greatest advice you’ve been given?”

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  1. Questions like this can tell you a lot about her goals and what she values. Keep the question random and fun, but give her the opportunity to share something more personal if she wants. [19]

Expert Q&A

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  • Question
    How do you ask a girl intimate questions?
    John Keegan
    Dating Coach
    John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.
    Dating Coach
    Expert Answer
    Make sure that the setting and tone of your date fit that type of conversation, as you don't want to come off as creepy. If you're okay with moving the date away from any friend zone vibes, you could move the conversation to a more intimate zone with a question like "What's the weirdest place you've ever had sex?"
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      Tips

      • Be genuinely curious about the answers she gives you! Listen to her and explore her response.

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      • Keep in mind that any one of these great questions could blow the conversation wide open, so there's no need to ask a specific number of questions.
      • You don't need to ask a bunch of questions. One or two questions can lead to an hour or more of flowing conversation.
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