Cute Flirty Questions to Ask Your Boyfriend

Did you know that asking cute and flirting questions is an ongoing process? Not just in early courtship and not just when things are getting serious. But even after sex, after engagement, and yet after marriage it’s very important to keep that cute and flirty dynamic going. It’s fun. It’s exuberant. It really helps to bond the two of you together.

But at some point, you might feel like you’ve run out of things to say. You might even think to yourself, “Oh no have we run out of things to talk about or joke about?

Of course not. There’s nothing wrong with settling down into a comfortable routine. What might help is to read some other questions that other people have come up with, and even some questions that I developed for this blog. Feel free to steal these or adapt them to your own lives. Let’s start the list of questions, shall we?

1. When’s the first time you thought about kissing me?
2. What’s my most attractive physical feature?
3. Do you like it when I caress your face?
4. Would you ever want to take a bubble bath with me?
5. If you have to describe me in two sentences what would you say?
6. What is something I don’t notice about myself that you always notice?
7. What are my biggest flaws that you’re afraid to tell me?
8. What’s a wild fantasy you’ve always wanted to try in real life?
9. Have you ever had a dream about me?
10. Have you ever fantasized about me and what happened in the fantasy?
11. What is your top favorite memory with me?
12. How would you cheer me up when I’m down?
13. What’s something you’ve never told me?
14. What’s something you’ve never told anyone else?
15. What is your favorite breakfast, lunch, and dinner?
16. What do you love about your family members?
17. What is something that I do that embarrasses you?
18. When was a time you laughed the loudest in your life?
19. What’s a secret that you keep hidden in your bedroom?
20. Who is your top hottest celebrity?
21. Who of all the people you know, understands the real you?
22. When was the first time you fell in love?
23. What’s something you’re afraid to tell me?
24. What’s something you think all the time which you’re afraid might offend me?
25. How do you get along with your parents, siblings?
26. What is the worst thing a guy can do on a first date?
27. What famous person would you definitely not want to marry?
28. Name three famous people you would have to kiss, kill or marry.
29. Do you believe in twin flames or soul mates?
30. What was your second choice for a career? What about the job appealed to you?
31. Were we destined to be together?
32. Before we were together, did you ever think anything bad or funny about me?
33. What was your first impression of me?
34. When did you first think I was really attractive and that you wanted to get to know me?
35. What’s your kinkiest fantasy involving me that you’re afraid to admit?
36. What was your most embarrassing moment?
37. Who is your favorite role model and why?
38. What country would you want to visit for a romantic weekend getaway?
39. What would be your favorite quiet date night with just the two of us?
40. What song tells the story of your life?
41. What’s your favorite book or movie?
42. What’s the worst job you’ve ever had?
43. What would you first do if you were a billionaire?
44. What’s the most important quality that a potential partner woman has?
45. When was a time you remember where you did something completely spontaneous and unpredictable…and it turned out great?
46. What’s something that you’ve done that’s amazing or unusual?
47. Who is the family member or friend you trust the most? (Besides me!)
48. What’s one of your favorite old hobbies you don’t try anymore? (Why not pick it up again!)
49. If you were king for a day, what would be your first order?
50. What is something kinky you’re kind of intimidated by but still curious about?
51. If you could go back in time what period would you want to see the most?
52. Catch him looking and then say, what were you thinking just then with that smile on your face?
53. What’s the most frightened you’ve ever been?
54. What time of day are you the most sensual and passionate?
55. What activity or thing instantly puts you in a good mood even after a bad day?
56. What did you used to want to be when you were a kid?
57. What is the one fantastic thing you think might exist in the real world?
58. Who’s someone from your past you lost track of but miss a lot?
59. What was your favorite subject in school?
60. If you could dress me in any outfit what would it be?
61. Who was your worst enemy in school / college?
62. How do you feel when a woman makes the first move romantically?
63. Who was your favorite TV character crush?
64. What kind of emotions or thoughts does your favorite hobby evoke?
65. Who was your first pet and what was its name?

You will find that most love the idea of answering questions. It lets them feel smart and witty. Asking questions encourages him to laugh, think, and feel. If you can keep the questions flirty and cute, maybe a little sexy, and a few serious and reflective, you will always be able to hold his attention.

Remember, these are not just to keep his mind occupied, but also to “learn him” and how he views life. You can learn a lot from a guy from the way he flirts or responds to your flirty questions. Take mental notes and determine what conversations get the most response. Over time, you will get him thinking, feeling and talking – and that means he’ll be more involved in the conversation. Flirting with your boyfriend isn’t just something you do as foreplay. It’s truly an amazing experience to have a strong bond with someone you care about.

Your bond together will only grow stronger as you keep flirting through the years, treating each other respectfully but always in a spirit of fun and gentle teasing.