75 Fun And Flirty Questions To Ask Your Boyfriend Over Text

Dating experience | | , Literature & Intimacy Writer
Updated On: December 21, 2023

The best way to get to know your partner better is by asking them interesting questions. These queries don’t just spark conversations but can also help you out if you feel your relationship is stuck in a rut. So, if you’re both into texting or your relationship has turned long-distance recently, you might be in need of some new questions to ask your boyfriend over text. In that case, you’re in the right place. 

Since you’re still getting to discover each other, we recommend you to prepare a list of questions to ask over text to keep a conversation going. Whether you’re just bored, or have reached the saturation point as far as information about your boyfriend is considered, this is a good tactic. Whether you’re looking for juicy questions to ask your boyfriend over text or romantic ones, this article contains a big list of them all!

Fun Questions To Ask Your Boyfriend Over Text 

To ensure your relationship is fun and refreshing, it’s important you keep each other on your toes – in a good way. You might feel like you’re out of topics to talk about with your boyfriend over text at night. But that’s a problem that can be rectified pretty easily. If you prepare a list of questions to ask your boyfriend over text when bored, you’ll never be out of topics to talk to him about. And these texting games actually turn out to be really fun sometimes.

Depending upon how your boyfriend’s mind works, you’ll either get some nonsensical answers, or you’ll get some truly insightful ones. You’ll unearth interesting information about him that you can use to hold long discussions afterward. But keep a few things in mind:

  • Ensure the questions are light-hearted and not about any serious matter
  • Pick the right time to ask these questions
  • Don’t put too much pressure on him to answer these the way you want to
  • Don’t ask these in one go

Having some funny online dating questions on hand helps a lot. Whether you wish to know what the strangest thing is that he owns, or want to know his favorite Die Hard movie or how he desires you in bed, these conversations will help. So, scroll ahead and you’ll find a big list of fun questions to ask your boyfriend to keep the conversation going all night long. 

1. What’s the strangest thing you own?

2. What was your favorite vacation as a child?

3. What if we ran away to a new country?

4. What’s the weirdest food combination you love?

5. A bad decision you made that turned out good?

6. What’s one routine you stick to no matter what?

7. Would you choose a cat or a dog as a pet? Why?

8. What’s the most underrated/overrated TV show according to you?

9. Do you believe in any conspiracy theory?

Related Reading: How To Get Someone To Stop Texting You Without Being Rude

10. Would you ever fart in front of me?

11. What’s the best advice you’ve given someone?

12. What’s your favorite motivational quote?

13. Would you prefer to be a math wizard or a literature buff?

14. What’s one book world you’d like to live in?

15. What color describes you the best?

16. What’s a reality TV show you’d want to go on?

17. What’s one thing you appreciate about your best friend the most?

18. What natural element would you want to have control over?

19. If I asked you to cook something for me, what would you make?

Flirty Questions To Ask Your Boyfriend Over Text 

Once you are in a relationship, you might be in need of fun topics to talk about with your boyfriend over text at night. Night is when the naughty secrets spill out and if you want to have a heartfelt conversation with your boyfriend, this is the best time to do it! After all, the best conversations mostly just happen at night, right?

Asking questions is a great way to reinforce your relationship. And if the questions are flirty enough, they’re a great way to add spice to your sex life. Just keep in mind, though, that flirting via text is not similar to sexting. But if done right, flirty texting can add another level of spice to your relationship.

  • Don’t forego subtlety 
  • A little cheekiness will not go amiss
  • Be intentional with your pick-up lines and cheesy quotes

Finding the right groove for your relationship can be a little tricky sometimes. But if you’re feeling particularly daring, these questions will come in handy. If you use this list of juicy questions to ask your boyfriend over text, seducing him will become a lot easier for you. 

20. When we meet, will you make the first move, or should I?

21. What is your favorite kink?

22. How good a kisser do you think you are?

23. What would you want to do to me if you were here?

24. If we only had one night together, what would we do?

25. What is your favorite place to leave a hickey?

26. If I tell you I’m not wearing a shirt right now, how would you react?

Related Reading: How To Respond To A Breakup Text

27. What’s the weirdest place you’ve made out in?

28. What’s your go-to move while making out?

29. Don’t worry, I won’t bite you. Unless you like that?

30. What is the weirdest kink you’ve ever had for a partner? Or what was ‘their’ weirdest kink?

31. How do you deal with sexual tension with someone at work?

32. How would you describe the perfect kiss?

33. What’s a fantasy you wish to enact? 

34. What is the most attractive body part according to you?

35. What’s your favorite pick-up line?

36. Do you like dirty talk in the bedroom?

37. What food combination is sexy according to you?

38. What is the one thing you’d like me to do to you?

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Romantic Questions To Ask Your Boyfriend Over Text

Here’s another set of topics to talk about with your boyfriend over text at night. Heartwarming conversations don’t need to be about complex stuff. Whether you’re new to dating him, or you both talk so much that you’re no longer left with anything to talk about, these questions can help. If you’re apart, having a set of romantic questions to ask your boyfriend over text can help further the conversation smoothly. Getting to know the other person doesn’t need to be complicated, and these questions make things easy.

Let’s gain an insight into your other half’s personality. These romantic questions can include his preferences, what makes him tick, or even his expectations from this relationship. To ensure you’re not misusing these romantic topics, keep the following in mind:

  • Asking the right romantic questions can actually help bring you both closer together
  • These questions can make you better attuned to each other’s personalities and needs
  • Frame the questions correctly and you’ll even gain more appreciation for each other
  • These will enhance communication between you both, and strengthen your bond

The following is a list of romantic questions you can ask your boyfriend. You can take this list out whenever you feel that the conversation is going stale. Or for a fun discussion when you’re both apart from each other. These questions are an excellent way of getting to know each other, so use them well! And if you are up for it, you can also use some what-if questions about love to have a serious conversation.

39. What was it about me that made you fall in love?

40. Do you ever imagine us living together? 

41. Would you like to slow dance with me in the refrigerator light?

42. What’s your favorite thing to do on our date nights?

On Romance

43. Do you think I might be the one?

44. On a scale of 1–10, how happy do I make you?

45. Where do you see our relationship in 5 years?

46. Do you have a favorite romcom?

47. If I ask you to plan a romantic date for us, what would it look like?

48. Which song do you think best describes our relationship?

49. Do you think our meeting was fate?

50. What is your vision for our wedding?

51. Do you think I have changed since we started dating?

52. What’s your love language?

53. What’s your favorite thing about our relationship?

54. If I were to ask you to give me a nickname, what would you call me?

55. What’s the craziest thing you’d do for love?

56. Do I make you feel safe?

Related Reading: 69 Tinder Icebreakers That Are Sure To Yield A Response

Random Questions To Ask Your Boyfriend

How well do you know your partner? Whether you’ve been together for a few months or a few years, there are probably things about your boyfriend you don’t know. And if you’ve been dating for years, chances are you might have run out of topics to talk about. Romantic and flirty questions are all well and good, but if you really wish to get to know your boyfriend better, random questions are what you should opt for. 

These topics can unearth so much about your boyfriend that you might be surprised. If you’re curious about what goes on in your boyfriend’s brain, asking him some random questions over text will keep the conversation flowing smoothly and get you the answers you so badly want. These questions can be asked over text or on your next date night; they’ll work great in both situations to start conversations.

57. If I gave you free reign to ask me anything, with the assurance I won’t get offended, what would you ask me?

58. Do you believe in the concept of soulmates?

59. What is something you’ve never told me before?

60. If you ever had to be a fish, what type of fish would you want to be?

61. What is your take on the red string of fate?

62. Do you think we have a guardian angel?

63. What is your favorite book trope? 

64. Have you ever doubted the existence of others?

65. What would you eat if you were living in a dystopian society?

66. What would you do if you were in a horror movie?

67. What’s the most interesting conversation you’ve ever had?

68. What is the strangest place you’ve ever fallen asleep in?

69. What is your most obscure interest?

70. What’s the most interesting piece of gossip you’ve ever heard?

71. Do you think aliens would like ice cream?

72. What’s the worst haircut you’ve ever had?

73. Your worst memory as a high schooler?

74. Would you ever eat earwax-flavored candy?

75. What’s the best part of rain to you?

Related Reading: 40 Best Opening Lines For Online Dating

Key Pointers

Key Pointers

  • Having a list of questions to ask your boyfriend over text will keep the conversation going all day or all night
  • These questions are good for any scenario: if you’ve just entered a relationship with him, if you’ve been together for years, if your relationship has become long-distance, if you’re trying to reconnect with each other, etc.
  • You’ll get to know a lot more about your partner through these topics, you will get closer to one another, and they might just end up surprising you with their answers
  • When you have a list of questions to ask your boyfriend over text when bored, conversation becomes a lot easier and helps you get out of relationship rut as well

This article has 75 fun and flirty questions to ask your boyfriend over text – you can take your pick and once you have the answers, you’ll know your boyfriend much better. It’s natural to be curious about how he perceives you and your relationship. And if you feel the spark is missing, these questions will certainly come in handy to restore it. 

But keep in mind that you shouldn’t throw a barrage of questions at your partner out of the blue. Use these sporadically and tactically. Try to weave them into conversations seamlessly and build upon his responses to have a fun and flirty conversation. Now that you have this list of interesting questions to ask over text to keep a conversation going all night long, let us know how it goes with your partner!

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