181 Flirty Questions To Ask Your Crush to Win Their Hearts

Have you gotten interested in that person and want to have a back-to-back convo with them to keep a bond between you two? It’s such an amazing feeling to finally find someone you crush on and want to talk to them all day. You either want to get to know the person a little or much better by asking lots and lots of questions. It’s okay to be flirty.

Sometimes, communication with your crush can be boring, and might seem you’re just asking interview questions. And more often, you repeat the same question over and over again without knowing it. There are ways you can be a little flirty and have romantic communication with your crush.

Trust me, they will want to come to your DM and continue with the amazing convos with you because those sweet words keep them smiling till the end of their day.

You know that kind of feeling you get when you’re so into a person you want to spend the rest of your life with? That kind of a “wow” feeling that wants you to let them know that you’re still thinking about them:

Talking to someone you’re into can be nerve-wracking enough without mentally tricking on what to say, and what not to say list in your mind. And if you need a little help in pushing your convos that sound flirty and could seem like Truth or Dare, then I bet you’re in the right place in your search.

Here are some flirty questions you can ask your crush. Whether in person or by text. I hope it helps you keep up with your crush so you both can have happy moments or convos together.

In this article, I have grouped them into three parts;

• Deep questions to ask your crush
• Good questions to ask your crush
• Flirty questions to ask your crush

1. Deep questions to ask your crush

1. Have you been in love before? What was the feeling like?
2. What’s your take on polygamy or monogamy?
3. Why would you prefer court marriage to church marriage?
4. How did your last relationship end? And whose fault?
5. Have you ever broken someone’s heart?
6. If you had three wishes on your wish list, what would be the first thing you wish for?
7. What was the kindest thing someone did for you?
8. Have you ever had your heart broken, and how did you handle it?
9. What is beauty to you?
10. Do you have any love languages? Tell me about it.
11. What’s your take on homosexuals?
12. Do you see yourself as someone who can keep secrets?
13. Describe yourself using your zodiac sign.
14. Who in your life do you look up to the most?
15. How did you meet your last partner?
16. Your mother or father—with whom do you like to spend quality time the most?
17. What’s the one thing that you would want to learn more about?
18. What you want to achieve and who you surround yourself with, which matters more to you?
19. Whenever you’re stressed or facing anxiety, what do you do to calm yourself down?
20. How do you approach conflict resolution style?
21. When was the last time you felt inspired to create something, and what did you create?
22. What would you consider your proudest accomplishment to be?
23. Have you ever rendered an apology to someone even when you weren’t at fault?
24. What is your most embarrassing moment in life?
25. If you had two things to compromise on what would those be?
26. The world is full of hate and jealousy, what would you want to change?
27. What traits do you think are most important to find in your partner?
28. Have you ever been cheated on?
29. What’s the worst thing about dating you?
30. What are your weaknesses and your strengths when it comes to dating?
31. What have you done in your life to be happy with the rest of your life?
32. Would you rather prefer to be paid well for a job or be paid less for something you’re passionate about?
33. Do you want to have kids someday and how many do you want to have?
34. What’s your take on relationships and religion?
35. What do you want to be remembered for?
36. What’s something interesting you would like to do in your next relationship?
37. Are you a quality or quantity person when it comes to relationships?
38. What is the most eventful year in your life?
39. If you had the chance to change something about yourself, what would that be?
40. What’s that one thing you see as a relationship dealbreaker?
41. Do you consider yourself a trustworthy person?
42. Would you want to get married someday?
43. Where do you see yourself in the next ten years of your life?
44. Would you consider yourself a relationship person or someone who is generally more of a single person?
45. One interesting thing about dating you?
46. Who is your favorite cousin?
47. When you’re alone, what do you do?
48. One thing you admire about your ex
49. What is one piece of advice you would want to give to your younger self?
50. When you find yourself in a new relationship, are you someone who wants to take things slow or moves pretty quickly?
51. Whenever you’re stressed or facing anxiety, what do you do to calm yourself down?
52. In what way do you think we’re similar?

2. Good Questions

1. What are the three pieces of advice you will give to someone who wants to give up on life?
2. Do you love to travel?
3. Do you love adventure? ( insert in names of adventures.)
4. What is your zodiac sign, and do you believe in it?
5. What’s your birthday?
6. Have you ever done any charity work?
7. Where is your favorite hangout?
8. You’re given a chance to be someone in just a day, whom would you want to become?
9. What is the best new artist/ song you have discovered recently?
10. Who is your favorite author?
11. How many books have you read this year?
12. Which do you prefer: rom-com, adventure, horror, or just romance?
13. I love tattoos; do you have one?
14. What’s the first movie you remember seeing in the theater?
15. What’s the worst date you’ve ever been on?
16. One thing you like and wouldn’t want people to necessarily guess about you?
17. How many friends do you have?
18. Do you have any best friends?
19. What’s your religion?
20. What would you consider your no.1 best movie of your lifetime?
21. Who is your favorite producer of all time, and which three movies?
22. Do you remember how your first kiss felt like? And with whom?
23. Are you a player?
24. What are you proud of about yourself?
25. Would you describe yourself as someone who likes to plan ahead or be spontaneous?
26. What’s one thing you think you spend way too much money on?
27. What’s that one food you would like to eat over and over again without getting tired of?
28. Describe your luckiest moments in life.
29. Have you ever asked your parents why they gave you (the person’s name) and what it means?
30. would you say you’re a superstitious person?
31. Have you ever had a supernatural experience?
32. Two places you would want to spend your vacation
33. What is your temperament?
34. What’s something you’re looking forward to?
35. What would you be doing if you weren’t (working or studying)?
36. Would you rather give money as help to someone or show them how to make money?
37. Do you have any favorite sports? What sport?
38. Your most hated movie of all time?
39. What’s something that you describe as guilty of pleasure?
40. Describe yourself using an animal. E.g., cat, dog, monkey, chicken, turtle, and why?
41. What was your favorite rhyme during your nursery days?
42. What’s your go-to karaoke song?
43. What is one thing you consider guilty of pleasure?
44. What one thing do you wish you could go out of style with?
45. Do you prefer trendy stuff or old-fashioned?
46. Do you consider yourself a competitive person?
47. What was your highest grade in your final exams?
48. Which teacher was your favorite, what subject, and why?
49. Most hated teacher of all time?
50. Your favorite subjects during your school days or in school (if the person is still schooling)
51. What’s one thing you think you spend too much time on?
52. Most hilarious moments in your life.
53. How many siblings do you have? Where do you fall?
54. Are you someone who gets bored easily?
55. What irritates you most in a relationship?
56. Have you ever done charity work? What was it?
57. Do you have any favorite childhood memories?
58. Where are the next three places you would love to travel to?
59. Have you ever fought outside with somebody before?
60. Who would you rescue—your mother or father?

Read Also;

• 10 Signs To know Your Partner Is No More Interested In You.

3. Flirty questions

1. What’s the most romantic moment you ever had with your partner?
2. Would you prefer to have a walk at the beach or have a drink at the mall?
3. What was your first kiss like?
4. Have you ever taken a risk for someone you love?
5. How would you define sex appeal?
6. Have you ever had sex at the beach?
7. Have you ever fallen for someone you met for the first time?
8. Most the craziest thing you ever did in a relationship?
9. Do you consider yourself a good kisser?
10. What would you do if we were both locked in a dark room?
11. If I asked you to be mine, what would be your answer?
12. What is something that attracts you easily to someone?
13. What makes a perfect date, in your opinion?
14. What is your love language?
15. What were your first impressions of me when we met?
16. You have a cute lip, and I think you wouldn’t mind if I have a taste of it.
17. How can someone earn your trust?
18. I hope you don’t mind me asking you to be mine forever.
19. What are your two greatest turn-ons?
20. Do you have a spec for the partner you want to date?
21. Why did you appear in my dream last night?
22. You know you have an amazing (add the feature) that everyone would want you to be theirs?
23. What’s that wow factor that will make you get closer to someone you wanna date?
24. Sex on the first date or nah?
25. What’s your take on a first kiss on a first date?
26. How many times do you think about me in a day?
27. Would it be cool if I asked you out to be my( insert what you want the person to be)?
28. Would you want to see what I am putting on? I want to have your take on it.
29. Have you ever thought of having a threesome?
30. If I were your pet, what name would you give me?
31. Why do I love talking to you this much? What did you do to me?
32. Tell me why I always smile anytime I see your text.
33. I wanna kiss you right now, do you think I am okay thinking about that?
34. Have you ever thought of dating someone right now?
35. If you had the chance to do something to me right now, what would that be?
36. What’s the most romantic thing your partner ever did for you?
37. What’s the most romantic thing have you ever done for your partner?
38. The craziest thing you and your partner did
39. Do you think I am qualified to be yours?
40. When am I seeing you?
41. When would you tell me you love me?
42. Craziest place you ever made love with your partner,
43. I hope I am not going to lose you to anyone.
44. When I touched you, how did you feel?
45. Can you look into my eyes and tell me how much you love me?
46. If we were to travel the world together, where would you want us to go first?
47. How many babies do you want to make with me when I finally become yours?
48. I am a( insert your zodiac). Do you think we will be perfect together?
49. Would you be happy to spend 24 hours with me in one room?
50. What would you have done if I didn’t accept being yours?
51. Can I see you this weekend?
52. Why do your thoughts give me butterflies in my belly?
53. I find it so hard to sleep lately. Do you think I might have fallen in love with you?
54. You’re cute, and I am also cute. Imagine the beautiful babies we are going to make if we are together.
55. What’s your go-to feature in someone you want to be with?
56. Have you ever tasted( insert the dish)? I would love to make you one.
57. Would it be alright if I hold your hands when we meet?
58. Can I steal you from your friends this weekend? I want to be with you.
59. If I were to propose to you right now, what would be your answer?
60. Is it okay if I kiss you when we meet?
61. Did you notice how happy I was when I was with you?
62. Can we be like this forever? I don’t want this feeling to go away. It is a good one.
63. Have you ever dreamt about us?
64. When we both left on a roller coaster, what would you do to me?
65. Do you know some steps? I want to have the first dance with you at the party.
66. How about a date night in my bedroom?
67. Has anyone ever told you how romantic you are?
68. Do you know you’re a very good kisser?
69. You have the best eyes; how come I am now noticing it?
70. Has anyone told you how gorgeous you are today?

Read Also;

• 5 Questions Ladies Do Not Want To Be Asked On A First Date.