135 Interesting Questions to Ask Your Crush, IRL or Over Text

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We get it — talking to someone you like in that way can be nerve-wracking. This is why you should always be prepared with questions to ask your crush; if only to improve on the whole “So what are your hobbies?” line of questioning.

There’s a bit of an art to seeding a romantic interest with questions that help you both gauge compatibility and strike the balance of fun, flirty, and probing. In other words, you want to deepen your knowledge of this person. You don’t want it to seem like you’re interviewing them for a job or ambushing them (says the person known for asking “When was the last time you cried?” on first dates). Of course, it’s not like there’s a strict formula for things to ask your crush to follow here. Talking to someone you’re into can be intimidating enough without mentally ticking off a things-to-say, things-not-to-say list in your head! But if you need a little help pushing the conversation in a direction that’s equal parts flirty and insightful à la Truth or Dare, we’ve done some of the work for you.

Below, you’ll find the best things to ask your crush, whether you’re hanging with them in person or having a convo over text. From deep questions to fun and, shall we say, suggestive ones, toss one of these into the mix the next time you’re feeling a little tongue-tied. (P.s. Even if this person has graduated from crush to someone you’re seeing, these are still good questions to ask!)

Asking questions shows you’re interested in someone, and you genuinely should be if you’re crushing on them. So let’s get to it.

In this article, you’ll find:

  • Good questions to ask your crush

  • Deep questions to ask your crush

  • Flirty questions to ask your crush

Beginner questions to ask someone you like

We suggest starting small before diving directly into their deepest, darkest fears. Sure, that’s where all the intimate details may be, but you have to earn that. Start with the basics and work toward more interesting parts of them as you go along. Don’t underestimate the power of the old-fashioned “How many siblings do you have?”

1. Where did you grow up?

2. What’s something you’re looking forward to?

3. What’s the best compliment you’ve ever received?

4. In what ways do you think we’re similar?

5. Sweet or savory breakfast?

6. What’s your current hyperfixation meal?

7. Are you a morning person or a night owl?

8. Favorite app on your phone?

9. Where do you stand on reality TV?

10. What’s something you’ve done that you think everyone could benefit from trying?

11. What’s your favorite meal to eat?

12. What’s your favorite meal to cook?

13. What’s your favorite restaurant?

14. Appetizers or dessert? Or both?

15. What would you be doing if you weren’t (insert job title or what they’re studying)?

16. What’s your favorite place you’ve traveled to?

17. Where are the next three places you want to travel?

18. What were you supposed to be named?

19. What was your college experience like?

20. What was your high school experience like?

21.. How do you recharge — on your own, or around other people?

22. Who’s your favorite author?

23. Do you prefer movies or TV shows?

24. Do you have any tattoos?

25. You’re playing hooky for a day. How are you spending it?

27. What’s something you like that people wouldn’t necessarily guess about you?

28. What’s the best new artist/song you’ve discovered recently?

29. What’s the first album you ever bought?

30. What’s the first movie you remember seeing in theaters?

31. How did you and your best friend meet?

32. When is your birthday?

33. What’s the worst date you’ve ever been on?

34. Do you think you’re like your zodiac sign?

35. Do you volunteer anywhere?

36. What are your four favorite movies?

37. What’s your favorite piece of random trivia?

38. What’s your favorite way to indulge?

39. What are you proud of right now?

40. Are you someone who gets bored, or not really?

41. Do you have any siblings?

42. Are you similar to your siblings?

43. Are you someone who likes to plan ahead or be spontaneous?

44. What’s one thing you think you spend way too much money on?

45. What was your luckiest moment in life?

46. What was the first musical artist or group you saw in concert?

47. What does your name mean, and why did your parents give it to you?

48. Would you say you’re a superstitious person?

49. Are you competitive?

50. On vacation, are you the hardcore R&R type or the person who has a full itinerary for every day?

51. Have you ever had a supernatural experience?

52. What’s something you wish would go out of style forever?

53. What’s something popular that you think is 100% deserving of its hype?

54. Are there things you like about being single? Things you don’t like?

55. Who’s a famous person you would definitely lose your cool around if you saw them on the street?

56. What’s your favorite movie to hate-watch?

57. What were you like as a kid?

58. What’s your go-to karaoke song?

59. What’s something you consider a guilty pleasure?

Deep questions to ask your crush

Once you’ve got the basics down and you think you’ve crossed the threshold of really getting to know each other, it’s time to take it deeper. Before asking these questions, it’s important to read the room. That’s how to start any conversation, but definitely one to strike up with a crush. Pay attention to their reactions or openness about certain topics. If they’re hesitant, we recommend not pushing in case they aren’t ready to open up quite yet. Be patient. Sometimes, they’ll offer deeper stories and thoughts organically throughout the conversation.

1. Do you believe in monogamy?

2. What’s your favorite childhood memory?

3. Are you close with your parents?

4. Have you been in love before? Who was your first love?

5. When was your first kiss?

6. When was your last relationship, and how did it end?

7. Have you ever been to therapy?

8. What’s the kindest thing someone’s ever done for you?

9. What’s the hardest thing you’ve ever had to do?

10. Do you believe in soulmates?

11. Have you ever had your heart broken?

12. Have you ever broken someone else’s heart?

13. Are your parents together?

14. What’s your love language?

15. Do you have any phobias?

16. What were you most scared of as a kid?

17. What’s your biggest fear now?

18. Is the approval of others important to you?

19. When was the last time you felt inspired to create something? What’d you create?

20. How do you like to be comforted when you’re sad or upset?

21. Who in life do you look up to most?

22. What’s the most rebellious thing you’ve ever done?

23. What’s something you’d like to learn more about?

24. Do people trust you to keep secrets?

25. How did your parents meet?

26. How would you describe your approach to conflict resolution style?

27. Do you think it matters more what we achieve or who we surround ourselves with?

28. What are your coping tools for dealing with stress or anxiety?

29. What would you consider your proudest accomplishment to be?

30. What do you think happens when we die?

31. What do you think you’ll be like in old age?

32. What’s something you’re unwilling to compromise on?

33. Have you ever been cheated on?

34. What traits do you think are most important to find in a partner?

35. What type of partner do you consider yourself to be?

36. What do you like most about yourself?

37. What’s one thing about yourself that you’d like to change?

38. Who in your family are you closest to?

39. Whose relationship do you admire and why?

40. What’s the worst thing about dating today?

41. Would you consider yourself a Relationship Person, or someone who’s generally more comfortable single?

42. What’s been the most eventful year in your life so far?

43. What’s something you see as being a relationship dealbreaker?

44. Would you consider yourself naturally trusting or a more guarded person?

45. Do you fall in love easily?

46. Are you a quantity or quality person when it comes to your friendships?

47. Who’s your oldest friend?

48. What’s something you’d like to do differently in your next relationship?

49. What’s something you wish you had a do-over on?

50. Would you rather have a job that’s just a job but pays well, or be paid less to do something you’re passionate about?

51. Do you want to have kids one day?

52. What’s your relationship to religion?

53. In relationships, are you someone who moves pretty quickly or takes things slow?

54. What’s your relationship to mental health like?

55. What do you want to be remembered for?

Flirty questions to ask your crush

The best part about getting your crush alone is the flirting. The same vibe check needed for the deep questions is essential for flirting as well. Once you’re pretty sure they’re into you too, you can steer the conversation in a more flirty way. Get as spicy as you’re comfortable and go with the flow.

1. If you were in a relationship right now, who would your celebrity pass be?

2. What makes for a perfect date, in your opinion?

3. What’s the most romantic thing someone has ever done for you?

4. What’s the hottest thing someone has ever done for you?

5. How would you define sex appeal?

6. Do you consider yourself a good kisser?

7. What’s something non-physical that you find attractive?

8. What makes you automatically swipe left on a person?

9. What was your first impression of me when we met?

10. Do you prefer other people to make the first move?

11. What are your top three biggest turn-ons?

12. What do your friends know about me?

13. I had this dream you were in last night. Want to hear it?

14. Has anyone ever told you how nice your (insert feature) is?

15. How does this look on me?

16. Why is it that I love talking to you this much? Any theories?

17. Are you interested in anyone right now?

18. Is it okay that I kind of want to kiss you right now?

19. What are you doing this weekend?

20. Have you ever been to (insert restaurant)? I’m dying to try it.

21. When am I seeing you next?

You might also want to check out: 21 Questions Game, 151 Questions to Ask Friends, Never Have I Ever Questions.

Originally Appeared on Teen Vogue