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. It’s also easy to take what you have for granted.

These cute questions 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?

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!)

8) Think back to the time we first met. What do you love the most about it? (Re-live the experience by reminiscing together!)

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’s three things you’d love to do with me – you’d love us to do together?

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!)

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?

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

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!

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

Psst, want to dig a little deeper? Keep getting to know your partner better? Then click here for 100 Personal Questions To Ask a Guy. It will seriously take your relationship to the next level!

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) 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!)

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

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?

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

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?

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

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

Recommended Read: 20 Romantic Things To Do For Your Boyfriend

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?

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?

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?

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?

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?

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!)

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

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

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?

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

69) 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.

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?

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

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 pet names for each other, what would you go for? What would you call me and what would you like yours to be?

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?

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!)

86) What does spending quality time together 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?

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.

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. Click Here For: 125 This Or That Questions For Couples

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 Ultimate Couples Question Game or these 20 Deep Questions To Get To Know Your Boyfriend Better?!

There’s also this one (it’s a big one!) – 50 Tough Relationship Questions You Really Should Ask Your Partner! So there’s plenty to keep you going there!

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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