I was chatting with a woman I liked one time. We had hit… dead air. You know that awkward point in a conversation when idle chit-chat just can’t carry the conversation any longer and you’ll literally do anything to find something meaningful to talk about.
It was around then that I learned an important lesson: If you want to make a real connection with someone, you have to ASK questions.
If you’re hoping to get closer to your crush but aren’t sure where to start, this guide is for you.
Below are 50 deep questions to ask your crush. Practical. Impactful. Romantic. I compiled this list so you can work these questions into your conversations and really understand who your crush is on a personal level.
Let’s jump in!
1. What’s your earliest memory that makes you smile?
We all have that adorable, happy-go-lucky moment in our lives that we’ll never forget. Not only does this question help break the ice, but it also allows you to see your crush’s cute or childish side
2. If you could relive any day of your life, which day would you pick?
You’ll get them to open up about a special memory they’ll never forget. It also helps you learn about important moments that have affected them.
3. What’s the most important lesson you’ve learned so far?
Life is a series of lessons. This question helps you determine what aspects of life they value most—whether that be love/relationships, family, career, or otherwise.
Read also: 18 Tips for Texting Your Crush
4. Who in your life has influenced you the most?
Digging deep into the heart always uncovers emotions. By asking who has influenced them the most, your crush will reveal who they look up to—whether that be a role model, family member, coach, teacher, friend, etc.
5. What’s your biggest fear right now?
Nothing says bonding like diving straight into a person’s deepest fears. Be careful with this question though, as you should prepare yourself to listen once they open up to you.
6. What’s something you’ve always wanted to try but haven’t yet?
The dreams we have (and don’t tell anyone) can tell you a lot about a person’s personality. You’ll find what their biggest ambitions are by asking this simple question.
Read also: 10 Signs Your Crush Likes You Back
7. How do you define success?
Is wealth important to your crush? Is happiness? Knowing how they define success allows you to learn what they care about when it comes to life.
8. What’s the most challenging experience you’ve ever faced?
You never know what your crush has been through. By hearing about the toughest times in their life, you’ll gain a deeper understanding for who they are as a person and admire their story.
9. What’s one habit you wish you could change about yourself?
We all have our quirks. See what your crush wishes they could improve about themselves. This is also a great question to ask if you know them well enough to playfully tease them about their habits.
10. If you could travel anywhere in the world, where would you go?
Asking about travel opens up a deep insight into their sense of adventure, curiosity, and personal interests.
11. What’s a book, movie, or song that really changed your perspective?
Similar to question #10, the media we digest help shape our world for the better. You’ll find common interests with your crush while uncovering deep insights about them by asking this.
12. What does your perfect day look like?
Dream questions always allow your crush to use their imagination and tell you a story. You’ll also learn what they value—whether that be relaxing, spending time with friends/family, or going on adventures.
13. How do you handle stress or difficult situations?
This question allows you to peek into how they keep their cool under pressure. You’ll learn about their emotional intelligence and how they reflect on important matters.
14. What’s your idea of a meaningful friendship?
The way your crush answers this question can tell you a lot about how they view romantic relationships. You’ll learn if they value honesty, loyalty, openness, etc.
15. What’s the most spontaneous thing you’ve ever done?
Every person loves to feel adventurous sometimes. This question allows your crush to show off their spontaneous side.
16. Do you believe in soulmates or fate?
This question goes DEEP. You’re diving straight into their beliefs about love and what it means to them.
17. What’s one thing that instantly makes you happy?
Want to know what truly makes your crush smile? Ask them this question. It also allows you to reward them with small gestures that will brighten their day.
18. What’s your favorite childhood tradition?
Traditions are important. Learn about what your crush valued as a kid—whether it be family, culture, or just fun memories.
19. What kind of people do you admire most?
You can tell a lot about a person by who they choose to look up to. Asking your crush this allows you to understand the qualities that matter most to them.
20. How do you usually spend time by yourself?
You learn a lot about a person by what they like to do when they have no one but themselves. Ask them this question to gain more insight into what truly matters to them outside of social outings.
21. What’s the best advice you’ve ever received?
The best piece of advice you learned early on was to always trust your gut. Everyone has that one person who they trust the most when it comes to advice. By asking this question, you’ll learn who that person is to your crush.
22. If you had all the free time and money in the world, what would you do?
Take this question beyond superficial things and dive into what your crush’s passions are. You’ll learn what they love to do that they wish they had more time to do.
23. What’s a misconception people usually have about you?
We all hate it when people try to label us. Let your crush clear up the rumors by telling you what qualities people assume they have.
24. Do you believe people can truly change?
This question goes deep into their beliefs on empathy and personal growth. You’ll determine if they believe people can learn from their mistakes by asking this.
25. How do you express love or affection towards others?
If you want to know if you and your crush will have a romantic connection, ask them this question. It allows you to peek into the way they give and receive love from others.
26. Have you ever had your heart broken? How did you deal with it?
Heartbreak is something we can all relate to. Not only will your crush open up to you by sharing their experience, but you’ll be able to support them by letting them know you understand how they felt.
27. What’s the most meaningful compliment you’ve ever received?
The best compliments we receive are the ones we never forget. You’ll learn some interesting things about your crush by hearing what compliments they cherish.
28. What makes you get out of bed in the morning?
We all wake up for different reasons. Some of us have jobs we love, others have families who depend on us. You can understand what your crush values most by asking this question.
Read also: 10 Hints to Give Your Crush Without Looking Desperate
29. How do you decide whether or not you can trust someone?
Learning if your crush is loyal allows you to determine if they’ll be faithful to you one day. You’ll understand how they judge others—whether they are quick to trust or never trust people again.
30. Do you prefer being alone or being around others?
This question is great for learning if your crush is an introvert or extrovert. You’ll understand what environments they feel most comfortable in.
31. What’s one thing you wish people understood about you?
Take this question as an opportunity to let your crush be vulnerable with you. More often than not, they will tell you something about themselves on a deeper level that they don’t normally share.
32. How do you deal with failure?
We’ve all had our fair share of failure. Ask your crush this question to learn about their ability to bounce back from disappointment.
33. What’s the most random compliment you’ve given or received?
This question is fun and allows your crush to share stories about their thoughtful or silly side.
34. What are the little things that make your day?
The little things in life are the important ones. As you learn more about your crush, be sure to look for the little things that they like to do to make their day better.
35. Do you believe in destiny? Or do we create our own?
Another great question to ask if you want to know your crush’s perspective on life.
36. What’s the hardest decision you’ve ever had to make?
No matter who you ask, we can all think of at least one hard decision we’ve had to make. You’ll gain a sense of your crush’s character by hearing about some of the tough choices they’ve had to make.
37. What’s your ideal way to spend a weekend?
Learn what your crush likes to do in their free time. You’ll discover what they enjoy—whether it be curling up with a good book or partying every night.
38. If you could learn one talent instantly, what would it be?
Everyone has hobbies they enjoy and others they wish they were good at. Let your crush tell you what hidden talents they’re willing to unleash on the world.
39. How important is family to you?
Family can tell you a lot about a person. You’ll learn if they come from a close-knit family or if they value friendships like family.
40. What’s the best surprise you’ve ever received?
Here’s a great question to help your crush express their romantic side. You’ll get them to tell you stories about their favorite surprises they’ve ever received.
41. What’s your favorite memory from growing up?
Whether it be funny stories from your childhood or daydreams, hearing about your crush’s favorite memories from youth will allow you two to bond over shared nostalgia.
42. Do you believe in forgiveness?
This question helps you understand how your crush handles conflict. You can tell whether they hold a grudge against people or believe everyone deserves a second chance by asking.
43. How do you celebrate your accomplishments?
Ever wonder how your crush shows themselves self-love? Some people like to treat themselves to new clothes when they succeed. Others like to take selfies. You’ll learn pretty soon.
44. What really grinds your gears?
Alright, this question may not be the deepest, but hearing what bothers your significant other is pretty interesting. Who knows, you may learn something that your crush does that you really don’t like 😛
45. What qualities are you looking for in friends or partners?
If you want a straightforward question that allows your crush to lay all their expectations on the table, this is it. You’ll understand what your crush is looking for in someone—whether that be honest, independent, or confident.
46. Do you have any weird dreams or nightmares?
Everyone’s subconscious tells a story. Let your crush wow you with some of their deepest fears and desires.
47. What’s something you used to believe in but no longer do?
Change is good. This question allows your crush to show off how they’ve matured throughout life.
48. How do you show someone you care about them?
This question dives deep into the way your crush shows love. You’ll be able to understand how they express affection—whether they are physical, mental, or emotional.
49. What’s one of your biggest secrets?
Guess what? You already know one of their biggest secrets. By asking them this question, your crush will become vulnerable and trust you with their deepest and darkest secrets.
50. What would you tell your younger self if you could?
Timeless advice never gets old. I love this question because people love to give advice. You’ll learn some meaningful advice your crush wished they knew when they were younger.
Final Thoughts
You’ve made it to the end! Asking deep questions is a great way to learn more about your significant other and better understand their values and personality. Use these 50 questions to ask your crush whenever you’re around them to create natural conversation, learn fun facts, and grow closer with them on a deeper level.
Just remember: the art of conversation isn’t only asking questions. Be sure to listen intently and respond thoughtfully to create a genuine connection with your crush.
Don’t just hear what they say. Listen.
FAQ
Q: Should I ask all 50 questions?
A: No! Sprinkle a few questions into your conversations when appropriate. You don’t want to interview your crush.
Q: What if they don’t give me long responses?
A: Push a little deeper. Ask them “Why do you think that?” or tell them your experience and encourage them to open up more.
Q: I only have a friend crush. Can I use these questions?
A: Absolutely! Many of these questions can be used to strengthen your friendships.
Q: How can I get my crush to open up to me?
A: Don’t jump into the deep questions right away. Work your way through them as you see if they’re comfortable sharing deeper information with you.
Q: My crush doesn’t want to talk about certain subjects. What should I do?
A: Respect their decision and move on. No one likes someone who pries into their business.
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