100+ Cute Questions To Ask Your Boyfriend

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Spending quality time with your partner? Looking for different questions to ask your boyfriend? Questions that will build closeness and connection? Then look no further. Here’s 100+ cute questions to ask your boyfriend – 100+ relationship questions to ask your boyfriend.

See, these questions focus on the two of you, your relationship and how your boyfriend feels. You want him to open up, be more expressive, and you will, of course, do the same thing too.

What makes these questions especially cute?

Because they’re reflective. They get you thinking, feeling, appreciating, remembering. 

It’s so easy to slip into routines in a relationship. In fact, taking a partner for granted is one of the most common bad habits in a relationship… Yet it’s a habit that’s so easy to slip into, and not even be aware of!

These cute questions, however, will remind the two of you just how special your relationship is. So let’s get stuck in…

100 Cute Questions To Ask Your Boyfriend

Here’s 100 cute questions to ask your boyfriend. Ask, listen, be responsive, engage. Then swap the question around and answer it yourself.

These cute questions are really going to bring closeness and appreciation in your relationship. So open up! Don’t be shy. Let’s get started…

1) If you could describe me in three words, what would they be?

2) If you could describe yourself in three words, what would they be?

3) How do you think we are similar? 

4) How do you think we are different?

5) And how do you think we complement each other? Why do we work so well?

Take it back to the early days of dating, when you started noticing the signs you’re falling in love.

What was it which made those feelings start to progress? How did you know he is “the one”? What about your boyfriend was different? And made you gel, so well?

6) If you could describe our relationship in three words, what would they be?

7) What are your top three favourite memories of us, and our relationship? (Or some of the best ones… I’m sure there’s heaps to choose from!)

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8) Think back to the time we first met. What do you love the most about it?

(Re-live the experience by reminiscing together! It’s one of the fastest ways to make you feel closer to your partner.)

9) What’s one little quirk you love about me? Or something that I do, that makes you smile?

10) What’s one thing you think no-one realises about me?

11) What’s one thing only I (or very few people) know about you?

12) What do you think is the best relationship advice we’ve ever been given? Or the best relationship advice you’ve heard?

13) How have we learnt and grown? Both as individuals since being together, and together, as a team?

14) What’s one thing you’re proud of? Both about me and about us?

15) What are three things you’d love to do with me – three things you’d love us to do together?

(Idea: You could build on this further, turning it into a couples bucket list planning free date night at home! The only rule? You have to schedule at least 1 thing from it, to start to make it happen!)

Cute Relationship Questions

Cute Questions To Ask Your Boyfriend

Onto the next set of questions? Are these questions bringing smiles to your faces so far? (I hope so!) So let’s keep them coming…

16) What’s your favourite kind of date?

17) What do you think my favourite kind of date is?

18) If you were going to plan a super extravagant surprise for me (and money wasn’t a cost) – what would you do for me? What do you think I would most like?

19) If you could buy me any gift – and money wasn’t a cost again – what would you buy?

20) If you could take me anywhere on a romantic get-away, where would we go?

21) What’s the most romantic thing you’ve ever done or would like to do?

(Consider the most romantic gestures done for your man, and use this question to plan more romantic things to do for your boyfriend! They can be both big and small!)

22) What’s your idea of dating hell? Which kind of dates would you least like to do and why?

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23) Okay, so, I’m going to cook you a special dinner (if you’re lucky, I really will!) – what would be your idea of the best meal? Let’s say starter, main and dessert – top choices?!

24) What’s one thing that I’ve done for you that surprised you? Or one thing that will always stick with you?

25) What makes me a great girlfriend?

26) What makes you a great boyfriend?

27) How could we be better partners? What could we improve on?

28) How can you tell when you’re really comfortable with someone? What’s the key indicators?

29) How long did it take you to feel totally comfortable around me?

Reminisce about some funny early stories! Use these funny questions to ask your partner if you’d like to increase the giggles, more and more!

30) What do you think would be TOO comfortable to do around a partner? Or are there no boundaries?!

Cute Relationship Questions To Ask Your Boyfriend

Relationship Questions To Ask Your Boyfriend

Let’s get him opening up about your relationship a little more! Here’s some cute relationship questions to ask your boyfriend – understanding how he truly feels.

31) What makes you feel close to me?

32) Do you think I can read you well? Or do I often not notice / interpret things wrong?

33) What do you think when you look at me?

(Be as expressive as you can with questions like this. Remember, there’s plenty of different ways to say I love you, and this is just one of them!)

34) What makes you feel vulnerable in a relationship?

35) Is there anything that scares you about being in love?

36) Do you feel like you can talk to me about anything and everything? Honestly?

37) Is there anything you wish we spoke about more?

(Some of these may sound like tough relationship questions, but they’re designed to bring you closer, which then of course, brings out the cuteness in the two of you!)

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38) What kind of things would you be worried about talking to me about?

39) Do you think we have good communication? Rate it on a scale of 1-10!

40) How do you think we deal with conflict? Do we have similar or different styles?

41) What’s your idea of the best way to “make up” after an argument?

42) What’s your love language? How do you best express your love?

43) What makes you feel the most loved? How do you like to receive love?

(Challenge: Once you know this, see how many different ideas you can come up with to make your partner feel loved… In the way which touches them the most!)

44) What do you think is the best way I could cheer you up if you were ever feeling down?

45) What does it feel like when you hold me? Kiss me? Touch me?

(Asking intimate questions in a relationship is important remember, so don’t shy away from these! It only helps to bring you closer.)

Cute Relationship Questions

Cute Questions To Ask Your Boyfriend

We’re heading up to the half way mark now, so let’s keep these cute questions to ask your boyfriend, coming!

46) What’s the best complement I’ve ever given you? Or the smallest, sweetest complement that’s actually meant the most to you?

(The better you can understand your partner and how to touch their heart, the stronger your relationship will become! Know how to make your partner feel good, to keep lifting them up and up!)

47) What would you do for me, that you wouldn’t do for everyone?

48) What are you and aren’t you, willing to change for a relationship? And what do you think about this topic as a whole – should you change for another person? In what ways?

This cute relationship question is actually super helpful, ensuring your relationship isn’t one sided, and the two of you are both in the same page – both “giving” and “taking.”

49) What did you think of me when you first met me? I mean, what were your first impressions?

50) What was the biggest thing that attracted you to me? How did I draw you in?!

51) How would you describe our first kiss? Do you remember it? (Again, Reminisce!) 

52) How soon did you know that you wanted to be with me?

(Or did you recognise the signs he wants you to be his girlfriend soon – early on!?)

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53) Was you ever unsure about how I felt or if we were on the same page?

54) When did you know that you’d fallen in love with me? And how did you know?

(Psst, see if this aligns with the signs he’s falling for you. How many of these could you spot yourself, at the time? And how many are so much clearer, when you look back on it now?)

55) What makes you love me more? And how have your feelings grown over time?

56) Are there any songs that remind you of me?

57) Which outfit of mine, do you love me in the most?

58) What do you most like my hair like?

59) If I was to significantly change my appearance, would you still fancy me?!

(Remember, there are ways to find someone more attractive and when you’re in love… you’re in love. Right? Or wrong?! You decide!)

60) What do you think makes a person most likely to fall out of love?

Relationship Questions To Ask Your Boyfriend

Relationship Questions To Ask Your Boyfriend

Let’s throw in some cute relationship questions to ask your boyfriend now – touching on some of the “serious stuff”. These questions always prove to be pretty insightful!

61) Do you think it’s easy or hard to fall in love? And how fast does it typically happen for you?

62) What do you think makes a relationship healthy, happy and long lasting? (Or ever lasting!)

(There are plenty of ways to make your boyfriend happy, but it should certainly be a two-way thing, which both people in the relationship, feeling the same way.)

63) How do you feel about marriage? Do you want to get married and have you always wanted to?

(This is a fun one now… See if you can spot the signs he sees himself marrying you!)

64) If you were going to pick our “first dance” song, what would it be?

(Here’s a roundup of the most popular first dance songs in 2023, to get you thinking!)

65) What would be your dream honeymoon? Where would you love to go?

66) What about children? Do you want them? If so, how many?

67) What do you think your parenting style would be? How would you be as a parent?

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68) How do you think I’d be as a parent? Who would be the soft one?!

69) If everything happens for a reason – why do you think we met?

70) Before you met me, what kind of things were you looking for in a partner, and how am I the same or different what you wanted / what you thought you wanted?

71) Have your views on love and relationships changed at all as you’ve got older?

Questions about love can be one of the most interesting cute questions to ask your boyfriend. Understand his opinions and views and see how well they align with your own!

72) What lessons have you learnt from your past relationships, which have enhanced ours?

73) Is there anything that scares you about being in a relationship?

74) Do you think there’s such a thing as soul mates? And how would you know if you found your soul mate?

75) What kind of life and future do you picture for yourself? Where do you see yourself (or us!) in 5, 10, 15, 20 years? etc.

Cute Relationship Questions

Cute Questions To Ask Your Boyfriend

76) What’s one thing you think you don’t tell me enough (if at all), but which you want me to know?

77) If we were to make new cute nicknames for each other, what would you go for? What would you like to call me and what would you like me to call you?

78) If I had to move really far away, would you move with me? We’re talking different city, different country even!

79) If we ended up in a long-distance relationship, would you stay with me? 

80) If you did stay with me (long distance) how would we make it work? (Discuss fun ideas you would do to keep it exciting!)

81) How do you feel when we’re apart? Or how would you feel if we had to be apart for weeks or months?!

(This will help to show how secure you feel in your relationship, and how secure your partner feels too! Remember there are plenty of ways to feel more secure in a relationship, so it doesn’t have to be anything to worry about.)

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82) Do you let me win games? (Be honest!)

83) What do you think is the nicest thing you’ve ever done for me?

84) What side of you do I bring out which is different?

85) Who do you think know’s who better? And who do you think is a more complex character? (Ha, be careful!)

Think you know your partner down to a tee? Then there’s also our Ultimate How Well Do You Know Me Question Game – to really put it to the test!

86) What does spending quality time in a relationship mean to you? And what would you class as quality time? Do we spend enough of it together? Have we got the balance right?

87) What’s the craziest thing you would do for me?

88) How would your life be different without me in it?

89) What does it mean to you to be able to trust someone fully? How much trust do you think we have in our relationship? And how do you think you can build trust in a relationship?

90) How does it make you feel when I tell you I love you?

Questions About Your Relationship

Think Of a Time That…

Let’s finish our cute questions to ask your boyfriend with “Think of a Time That…”

It’s pretty self-explanatory. You’ll ask for a certain type of time, and he has to share the first thing that comes to his mind when it comes to that.

So for example, you could try:

Think of a time that…

91) We laughed uncontrollably together.

(This is important! After all “couples who laugh together, stay together”, scientists have discovered!)

92) We did something wild together.

93) I made you feel proud.

Think of a time that…

94) Will always be special.

95) Means the most to you.

96) Shows just how good we are for each other.

97) Summarises our relationship perfectly.

Think of a time that…

98) Showed you why you want to be with me.

99) Showed you why you want to spend the rest of your life with me. (Eek!)

100) Showed me just how much you love me!

Like these short, snappy questions? Then you’re going to love our This or That Question Game. They’re fun, fast-paced questions you can play anywhere, anytime!

That’s All For This One

So there we have it. That’s a total of 100 cute questions to ask your boyfriend.

Liked this? Then why not try our Couples Question Game or Couples Trivia Game.

Remember, “what you put in, you get out” – like most things in life.

So keep working on the two of you, keep putting that time, effort, love and attention into it and keep opening up that conversation… Because it pays off, trust me.

Take care. Happy loving!


Cute Questions To Ask Your Boyfriend
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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