100 Questions to Ask Your Crush to Spark Meaningful Conversations

Starting a conversation with your crush can feel like navigating uncharted territory. What should you ask? How do you steer the conversation from light and playful to something deeper without coming on too strong? Whether you’re chatting face-to-face or over text, having the right questions ready can help you learn more about your crush and set the foundation for a meaningful connection.

At Pure Intentions, we believe in fostering deeper connections, so we’ve put together a list of more than 100 questions to help you get to know your crush on a more intentional level. These questions aren’t just designed to pass the time—they’re carefully crafted to reveal more about your crush’s personality, values, and desires.

Plus, for those moments when conversation alone isn’t enough, our Icebreakers Dating Game Cards and Pure Intentions Blocks provide thought-provoking questions to guide you toward a deeper understanding of one another.

Now, let’s dive into the questions that will spark a genuine connection:

I’m passionate about intentional dating, so I created the Icebreakers conversation starter cards. Imagine pulling out a deck of playing cards with interesting questions while on a date and transforming it into something spectacular! Here’s a handful of thought-provoking cards from one of the decks:

• What did love look like to you in your childhood?
• Everyone needs healing; what is one thing from your past that you feel is hard to let go of?
• If your ex could describe how you are in a relationship, what do you think they would say?
• If we were in a committed relationship and I had to move out of state, do you feel you would be able to handle that, and how?
• Name one experience you’ve had in your life that you would say has made the greatest impact on who you are today.

Good Questions to Start the Conversation

Start with these casual, light-hearted questions to break the ice and set the tone for an engaging chat.

• What’s your favorite way to spend a Sunday?
• What’s one thing you’ve always wanted to learn?
• What’s the best advice you’ve ever received?
• What’s your go-to comfort food?
• If you could live anywhere for a year, where would it be?
• What’s your favorite type of music?
• What’s your go-to weekend activity?
• Do you have any hobbies that most people don’t know about?
• If you could be any animal, what would you be and why?
• What’s your favorite way to relax after a long day?
• What’s the best meal you’ve ever had?
• If you could travel anywhere in the world, where would you go?
• Do you have any hidden talents?
• What’s something that always makes you laugh?
• What’s your favorite season and why?

Fun and Flirty Questions

Once you feel the vibe is right, use these questions to hint at deeper interest.

• What’s the most romantic thing you’ve ever done for someone?
• What’s your idea of a perfect date?
• What do you find most attractive in a person?
• What’s one thing you’ve always wanted to ask me but haven’t?
• Do you believe in love at first sight?
• What’s the most spontaneous thing you’ve ever done?
• What’s your idea of the perfect date?
• What’s the most romantic thing someone’s ever done for you?
• What’s your biggest turn-on?
• If you could plan the ultimate date, what would it be?
• What’s one thing you’ve always wanted to ask me but haven’t yet?
• Do you believe in love at first sight?
• What do you find most attractive about someone?
• What’s something you find irresistible?
• What would you say is your love language?

Deep Questions to Get to Know Them Better

When you’re ready to dig deeper, these questions will help you learn more about your crush’s personality, values, and life experiences.

• What’s a defining moment in your life?
• How do you handle stress and tough situations?
• What’s something you’re passionate about that you wish more people understood?
• What’s the biggest lesson you’ve learned in the last year?
• Who has had the greatest impact on who you are today?
• What’s the biggest challenge you’ve overcome?
• How do you handle stress or pressure?
• What’s a life goal you’re currently working toward?
• Who do you look up to the most?
• What’s the most important lesson you’ve learned in life so far?
• How do you define success?
• What’s something you’re passionate about that others may not understand?
• What’s the best decision you’ve ever made?
• What’s something you want to improve about yourself?
• What do you value most in a friendship or relationship?

Spicy Questions for a Little More Fun

When the conversation is going well and you both feel comfortable, add a little playful spice with these questions.

• What’s your biggest turn-on?
• What’s something you find irresistibly attractive about someone?
• Have you ever had a crush on someone you shouldn’t have?
• What’s a guilty pleasure of yours?
• Do you think we’d make a good couple?
• What’s your guilty pleasure?
• Have you ever had a crush on someone you shouldn’t have?
• What’s the craziest thing you’ve ever done for love?
• What’s something you’ve always wanted to try in a relationship?
• What’s your biggest fantasy?
• What’s something you find incredibly sexy about a person?
• Have you ever made the first move?
• What’s a flirtatious compliment you’ve received that you loved?
• What’s your favorite way to be kissed?
• Do you think we’d make a good couple?

Thought-Provoking Questions

• For a more introspective and meaningful conversation, these questions will get you thinking.
• What’s one belief you hold that you feel strongly about?
• What’s your favorite childhood memory?
• If you could change one thing about the world, what would it be?
• What does happiness mean to you?
• How do you think people grow and evolve in relationships?
• What’s something you’ve learned about yourself from past relationships?
• What’s the most important quality in a partner?
• How do you define love?
• What’s something you think everyone should experience at least once?
• What’s a cause you deeply care about?

Questions to Learn About Their Past

Understanding someone’s past experiences can give insight into who they are today.

• What’s a childhood dream you had that you never gave up on?
• What was your favorite thing to do as a kid?
• What’s the most memorable trip you’ve ever taken?
• What’s a mistake you’ve made that taught you something valuable?
• What’s one thing you miss about being younger?
• How did your first relationship end, and what did you learn from it?
• Who was your biggest influence growing up?
• What’s the scariest thing you’ve ever done?
• What’s one thing you would tell your younger self if you could?
• What’s something from your past you’re really proud of?

Funny Questions to Keep It Light

Keep things fun and lighthearted with these humorous questions.

• What’s the weirdest food you’ve ever tried?
• If you could have any superpower, what would it be?
• What’s the most embarrassing thing that’s ever happened to you?
• If you were a character in a movie, who would you be?
• What’s the most random thing you’ve Googled recently?
• If you could switch lives with any fictional character for a day, who would it be?
• What’s the funniest joke you know?
• What’s the silliest thing you’ve ever done to impress someone?
• If you were a meme, which one would you be?
• What’s your most irrational fear?

Romantic Questions for When the Time Is Right

Once things start heating up, try these romantic questions to keep the spark alive.

• What’s your idea of a perfect kiss?
• How do you know when you’re falling for someone?
• What’s your favorite thing about being in love?
• What’s the most romantic gesture you’ve ever made?
• What’s something small that can instantly make you feel loved?
• What’s your favorite memory of us so far?
• How do you show someone you care about them?
• What’s one thing you would never compromise on in a relationship?
• What’s a romantic fantasy you’ve always had?
• What’s your idea of a perfect romantic getaway?

Questions About Their Future

Looking to the future together? These questions can help you understand their aspirations.

• What’s something you hope to achieve in the next five years?
• Where do you see yourself living in the future?
• What’s one thing you’re working toward in your personal life?
• Do you want to travel a lot in the future?
• What’s something you’re excited to do in the next year?
• How do you imagine your dream life in 10 years?
• What’s a new skill or hobby you’d love to learn?
• What are your top priorities in life right now?
• How do you see your relationships growing over time?
• What’s a big goal you’ve always wanted to achieve?

Questions to Reflect on Your Connection

When the relationship starts progressing, use these questions to reflect on your connection.

• What’s something you appreciate about our time together?
• How do you feel when we’re apart?
• What’s your favorite thing about me?
• What’s something you think we could do to get closer?
• How do you think our relationship has grown since we first met?
• What’s a memory of us that always makes you smile?
• How do you feel about where we’re headed?
• What’s something you’re looking forward to doing together?
• What’s one thing you think I could do to make you feel more loved?
• How do you know when a relationship is worth fighting for?

Finding Meaning Through Conversation

Asking the right questions can make all the difference when it comes to building a meaningful relationship. By being intentional about the questions you ask, you can gain a deeper understanding of your crush and see if your connection has the potential to develop into something more lasting.

For more thoughtful questions to guide your dating experience, check out our Icebreakers Cards and Pure Intentions Blocks, both designed to help you take your conversations to the next level.

Ready to take the next step in your dating journey? Explore our Dating Games for interactive ways to break the ice and connect on a deeper level. Shop Our Dating Games!