65 Amazing Questions to Ask Your Crush


Opening hook

You’ve been eyeing that special someone for a while now, and you’re ready to take the plunge and strike up a conversation. But where do you start? Asking the right questions can be the key to breaking the ice and building a connection with your crush.

Importance of asking questions

Asking questions is a crucial part of getting to know someone on a deeper level. It shows that you’re interested in learning more about them and allows you to uncover common interests, shared values, and potential compatibilities.

Thesis statement

In this article, we’ll explore 65 questions to ask your crush to kickstart a meaningful conversation, build rapport, and potentially take your connection to the next level.

Building Rapport

Basic get-to-know-you questions

Before diving into more personal territory, it’s essential to establish a foundation of familiarity by asking some basic get-to-know-you questions.

Questions to Ask Your Crush


  • “Do you have any siblings?”
  • “What do your parents do for a living?”
  • “Are you close with your extended family?”

Hobbies and Interests

  • “What kind of activities do you enjoy in your free time?”
  • “Are you into any sports or outdoor activities?”
  • “What’s the last book you read that you really enjoyed?”


  • “What’s your favourite type of music?”
  • “Do you have a favourite movie or TV show?”
  • “If you could only eat one food for the rest of your life, what would it be?”

Finding common ground

Discovering shared interests can help you build a stronger connection and find common ground.


  • “What kind of music are you into lately?”
  • “Have you been to any concerts recently?”
  • “Who’s your favourite artist or band?”

Movies/TV shows

  • “What’s the last great movie you saw?”
  • “Are you currently binge-watching any shows?”
  • “Do you prefer comedies, dramas, or action movies?”


  • “Are you a fan of any particular sports teams?”
  • “Do you play any sports yourself?”
  • “What’s your favourite sporting event to watch or attend?”

Deepening the Connection

Personality questions

As you start to feel more comfortable with each other, you can delve into questions that reveal more about your crush’s personality, values, and life outlook.

Questions to Ask Your Crush

Values and Beliefs

  • “What are some of your core values or beliefs?”
  • “Is there a cause or issue you’re particularly passionate about?”
  • “How important is faith or spirituality in your life?”

Life goals

  • “What are some of your long-term goals or ambitions?”
  • “Where do you see yourself in 5 or 10 years?”
  • “If money wasn’t an issue, what would be your dream job or lifestyle?”

Relationship views

  • “What do you think are the most important qualities in a partner?”
  • “Have you ever been in a serious relationship before?”
  • “How do you feel about long-distance relationships?”

Thought-provoking questions

These questions can help you gain insight into your crush’s thought processes and stimulate deeper conversations.

Hypothetical scenarios

  • “If you could have dinner with anyone, living or dead, who would it be and why?”
  • “If you won the lottery, what’s the first thing you would do?”
  • “If you could live anywhere in the world, where would you choose and why?”

Philosophical questions

  • “Do you believe in fate or do you think we have control over our destinies?”
  • “What do you think happens after we die?”
  • “If you could change one thing about the world, what would it be?”

Deep conversations

  • “What’s the most important lesson life has taught you so far?”
  • “What’s your biggest fear or insecurity?”
  • “If you could go back and change one decision in your life, what would it be?”

Getting Flirty

Playful questions

Once you’ve established a comfortable rapport, you can start to inject a bit of playfulness and flirtation into the conversation.

Questions to Ask Your Crush

Funny scenarios

  • “If you were an animal, what would you be and why?”
  • “If you had to choose a superhero name, what would it be?”
  • “What’s the weirdest dream you’ve ever had?”

Silly would-you-rather questions

  • “Would you rather be able to fly or breathe underwater?”
  • “Would you rather have a pet dragon or a unicorn?”
  • “Would you rather never have to sleep again or never have to eat again?”

Flirtatious questions

  • “What’s your idea of the perfect date?”
  • “What do you find most attractive in a partner?”
  • “Do you believe in love at first sight?”

Complimentary questions

Offering sincere compliments can be a great way to show your interest and make your crush feel appreciated.

Physical appearance

  • “Has anyone ever told you that you have really beautiful eyes/smile/etc.?”
  • “You always look so put together. How do you manage to look so stylish all the time?”
  • “You have such a great sense of fashion. Where do you get your style inspiration?”

Personality traits

  • “You always seem so positive and upbeat. What’s your secret?”
  • “I really admire your confidence and ability to speak your mind.”
  • “You have such a great sense of humour. You always manage to make me laugh.”

Talents and Achievements

  • “I heard you’re an amazing singer/artist/athlete. How did you get started with that?”
  • “Congratulations on your recent accomplishment! That must have taken a lot of hard work and dedication.”
  • “I’m always impressed by how knowledgeable you are about (topic). How did you become so interested in that?”

Building Intimacy

Personal questions

As your connection deepens, you may feel comfortable broaching more personal topics that allow you to truly get to know each other on a deeper level.

Questions to Ask Your Crush


  • “What’s your fondest childhood memory?”
  • “Did you have any funny or embarrassing childhood stories?”
  • “What was your relationship like with your parents growing up?”

Fears and insecuritie

  • “What’s one of your biggest fears or insecurities?”
  • “Is there anything from your past that still haunts you?”
  • “How do you typically cope with stress or anxiety?”

Dreams and Aspirations

  • “If you could accomplish anything in life, what would it be?”
  • “What’s one dream you have that you’ve never shared with anyone before?”
  • “What’s something you’re really passionate about pursuing?”

Romantic questions

As you start to explore the romantic potential of your connection, these questions can help gauge your crush’s feelings and expectations.

Dating preferences

  • “What’s your ideal first date?”
  • “Are you more of a romantic or a pragmatist when it comes to relationships?”
  • “Do you prefer to take things slow or move quickly in a new relationship?”

Relationship expectations

  • “What are your thoughts on marriage and commitment?”
  • “How important is physical intimacy in a relationship for you?”
  • “What are some dealbreakers for you in a relationship?”

Intimate questions

  • “Have you ever been truly in love before?”
  • “What’s the most romantic thing anyone has ever done for you?”
  • “If we were to start dating, what would be your biggest concern or worry?”

Flirty Questions to Ask Your Crush

If you’ve got your eye on someone special, it’s time to break the ice and get flirtatious. Asking the right playful questions can help create a fun, flirty vibe and get you both feeling those butterflies. Here are 15 flirty questions that just might help you connect with your crush:

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  1. If you could only eat one meal for the rest of your life, what would it be?
  2. What’s your dream vacation spot?
  3. What’s something you’re weirdly good at?
  4. Do you prefer movies or TV shows? What’s your favorite?
  5. If you won the lottery, what’s the first thing you’d do?
  6. What’s the worst pick-up line you’ve ever heard?
  7. Do you have any pet peeves or weird pet names?
  8. What’s your go-to karaoke song?
  9. What takes up too much of your time that you wish you could quit?
  10. If you could star in a movie, what genre would it be?
  11. Have you ever had an embarrassing moment that still makes you cringe?
  12. What’s the most spontaneous thing you’ve ever done?
  13. What’s your spirit animal and why?
  14. What weird talents do you wish you had?
  15. If you could time travel, what year would you visit?

The best flirty questions are a mix of fun, playful, and just a little bit personal. Keep things light and listen closely to your crush’s answers – you might just learn something that could help you connect even more. Most importantly, relax and let your own personality shine through. Flirting should be all about enjoying each other’s company.

Questions to Ask Your Crush in Truth or Dare

Here are some good truth or dare questions to ask your crush in a flirty game of truth or dare:

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Truth Questions:
  1. Who was your first celebrity crush?
  2. What’s the most outrageous flirting attempt someone has tried on you?
  3. What’s your biggest turn-on?
  4. What’s your most embarrassing dating story?
  5. Have you ever had a crush on a friend?
  6. What’s the worst pick-up line you’ve ever used (or had used on you)?
  7. What’s your dream romantic fantasy?
  8. Have you ever been skinny dipping?
  9. When was the last time you were naked in public?
  10. Do you have any weird relationship dealbreakers?
Dare Questions:
  1. I dare you to let me put my number in your phone.
  2. I dare you to send a flirty selfie to someone in this room.
  3. I dare you to describe your biggest turn-on without using any words.
  4. I dare you to give me a piggyback ride for 2 minutes.
  5. I dare you to slow dance with me to no music for 1 minute.
  6. I dare you to send the person to your left a flirty text.
  7. I dare you to lick salt off the back of my hand.
  8. I dare you to wink at the person you find most attractive in this room.
  9. I dare you to blow in my ear seductively.
  10. I dare you to stare into my eyes for 30 seconds without laughing.

The key is to start mild and build tension, getting bolder as you go. Make sure to match the heat level to how well you know your crush. Truth or dare can be a flirty way to break the ice and create fun, flirtatious moments!



Asking the right questions can be a powerful tool for building a connection with your crush. By starting with basic get-to-know-you questions, finding common ground, and gradually delving deeper into more personal and intimate topics, you can peel back the layers and truly get to know the person behind the crush.

Final thoughts

Remember, the key is to strike a balance between showing genuine interest and respecting boundaries. Pay attention to your crush’s body language and responses, and don’t be afraid to follow their lead. With a little courage and the right questions, you might just turn that crush into something more meaningful.


Q: What if my crush seems uncomfortable or hesitant to answer certain questions?

A: If your crush seems uncomfortable or hesitant to answer certain questions, it’s essential to respect their boundaries. Don’t push too hard or make them feel pressured to share more than they’re comfortable with. Instead, steer the conversation back to more neutral topics and give them space.

Q: How can I tell if my crush is interested in me or just being friendly?

A: It can be challenging to read romantic interest sometimes. Pay attention to body language cues, such as maintaining eye contact, leaning in closer, playing with their hair or touching you casually. However, don’t read too much into these signs alone. Look for a pattern of behavior and responses that suggest a deeper connection.

Q: What if I run out of questions to ask?

A: If you find yourself running out of questions, don’t panic. Use the conversation as a jumping-off point to share your own thoughts, experiences, or stories related to the topic. Encourage your crush to elaborate or ask you questions in return. A good conversation should flow naturally between both parties.

Q: Is it better to ask questions in person or via text/online?

A: While some questions can be asked over text or online, it’s generally better to have more meaningful conversations in person. Face-to-face interactions allow you to pick up on important non-verbal cues and create a more authentic connection. Save the deeper, more personal questions for when you’re together in person.

Q: How do I know when it’s the right time to ask more intimate or romantic questions?

A: There’s no one-size-fits-all answer, as the right time will depend on the specific connection and comfort level between you and your crush. However, a general rule of thumb is to build up to more intimate questions gradually, rather than diving in too quickly. Pay attention to the flow of the conversation and your crush’s responses to gauge when it might be appropriate to take things to a deeper level.