120 Questions To Ask Your Boyfriend To Test His Love

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Are you looking for questions to ask your boyfriend to test his love? Questions to test his love which are designed to help you establish how he feels? And if so, how can you ask them properly so that it doesn’t come across as an interrogation, but instead – an interesting conversation? Well my friends, we’ve got you covered. As in this post, we’re going to break down it all.

Why Are You Testing His Love?

So before we jump into the questions themselves, I want to start by asking you, why? Why are you trying to test your boyfriends love? This is really important.

  • Is it because your boyfriend isn’t good at expressing himself, and you want a little clarity?
  • Or maybe it’s not clarity even – you simply want to hear how he feels for the… niceness of it all?
  • Are you seeking reassurance for your own self-doubt or insecurities?
  • Or seeking reassurance as your relationship is a little rocky and you genuinely don’t know how he feels?
  • Do you know you need to open up some conversations? Ask more of the intimate questions or tough relationship questions because you know that it will strengthen what you have?
  • Or are you worried he’s fallen out of love with you? [Click Here For The Signs!]
  • Has something bad happened in your relationship? Perhaps he’s betrayed your trust and so now you’re trying to decide if he deserves it back?
  • Or maybe “testing his love” isn’t quite as intense as it sounds? You simply want to ask a few questions and direct the conversation over to your relationship a little more? You’re doing this for a “bit of fun?”

Well for some more fun, lighthearted relationship questions, I highly recommend bobbing over to this article with 100 Cute Questions To Ask Your Boyfriend. (It’s got some of my favourite questions in there! There’s some really great conversation starters.)

Just make sure that if you’re going to fire through these questions to test your boyfriends love – it’s not driven by the wrong reason. It’s not toxic or unhealthy. Agreed?

Questions To Ask Your Boyfriend To Test His Love

So how do you ask these questions to test your boyfriends love? How do you go about it in the right way? Well, there’s a few “rules” before we go any further.

1) Pick Your Timing

If you’re going to ask your boyfriend these kind of questions, you DON’T want to ask them post-argument, or when he’s tired or busy.

You just won’t get the answers you want – or even the answers he necessarily means.

Instead, ask them when the two of you are good, and getting on. Ask them when you’re at home, chilling, or having a “heart to heart” conversation.

Or, ask them when you’re having a serious conversation. But make sure you’re both level headed.

2) Don’t Ask Them All In One Go

To avoid an “integration” feel, don’t get this list out, reading it down, one by one. No, no, no!

Instead, throw these questions into conversations where you can.

Read the list, remember the ones that stand out to you the most – the ones you most want to know – and start with those.

3) Listen To The Answers

If you’re looking for questions to ask your boyfriend to test his love – automatically – that doesn’t always put you in the best frame of mind. 

After all, if you see it as a “test”, you’re most likely to have a “right” or “wrong” answer in your mind. But this is the biggest mistake you can make.

Don’t make judgements. Don’t have expectations. And try not to be disappointed if your boyfriend doesn’t say the EXACT THING you wanted him to, or the exact thing that you would say. 

Everyone’s different, remember? So instead, ask these questions, be open-minded, really hear what he’s saying and try to understand it. Try to understand him.

BONUS: Remember, You Can Make This Fun!

The last thing I want to throw out there, is the fact that you may not be asking your boyfriend questions to test his love because you’re in a bad place! 

For this reason, I’m going to throw in some fun questions – questions that are most based on seeing how much he remembers about you and your relationship and how well aligned you are.

Does that sound good? Alright then. Then let’s get stuck in…

Does He Love Me?

120 Questions To Ask Your Boyfriend To Test His Love

Let’s get started with the questions now then. Here’s our top 120 questions to ask your boyfriend to test his love. In no particular order (and remember, don’t have any expectations or set answers in mind here. It’s not REALLY a test!)…

1) What’s your favourite thing about our relationship?

2) What’s your favourite thing about me?

3) What things don’t you like about me? Or which you would change about me if you could?

4) How do you think our relationship has changed (for better and for worse), since we first got together? 

5) How do you think we, as individuals, have changed (for better and for worse), since we first got together?

6) How well do you think that I know and understand you?

7) How well do you think that you know and understand me?

8) Are there any small things, that you love about me, that others perhaps don’t know or notice?

9) How would you describe me to someone who doesn’t know me?

10) How would you best describe our relationship?

Let’s Talk About Love…

11) At which point did you know that you’d fallen in love with me?

12) How did you know that you was in love with me?

13) And what does being in love feel like to you?

14) Have you ever had doubts about our relationship? And why? Where did they come from?

15) Have you ever had doubts about our compatibility? And why? Where did this come from?

16) Have there been any past experiences that have happened to you in relationships, that affects how easy it is for you to fully commit to me, or completely give me your heart?

17) Do you think any of my past experiences affect our relationship at all?

18) How certain are you about us and our relationship now?

19) Is there anything I / we could do to make you feel more certain about us?

20) What do you think is one area of our relationship we should / could work on?

How Does This Test His Love?

As you can see, these questions are designed to understand your boyfriends views on you, and your relationship. 

Remember, you’re not looking for him to not say ANYTHING negative. Love is loving a person for all their flaws and all. 

But within his answers, he shouldn’t be saying any things that are “deal breakers” to him. There should also be more positives than negatives over all.

Questions To Ask Your Boyfriend To Test His Love

21) Are there any things you think we’ve said we’d work on but which we haven’t?

22) Are there any things that you think should change, but you think won’t or can’t?

23) What do you think are the biggest challenges we’ve overcome in our relationship?

24) What are you most proud of us doing in our relationship?

25) In what ways do you think we work well together? What makes us good for each other?

26) Are there any things you think could get in the way of our relationship moving forward?

27) How committed are you to this relationship? What would you, or wouldn’t you be willing to do to make it work?

28) On a similar note: what sacrifices would you and wouldn’t you make, for our relationship? (And any relationships in general. What are your standards / morals around this?)

29) Can you genuinely see a future with me? 

30) Have you ever thought about us breaking up? (Be honest, I know this is a tough one!)

Let’s Keep Them Coming…

Remember, the way in which you ask these, the tone and the moment that you pick to ask them, will significantly change the way you come across. So be mindful of thing when asking your boyfriend questions to test his love…

31) Is there anything that I have done, that has affected the way that you feel? Anything that you’re finding difficult to let go of or forgive?

32) How confident are you about you and I, staying together “forever” (as cliched as that sounds!)?

33) What does our future look like to you? Realistically?

34) And what would our dream future look like – with everything you think it will be, and everything (and more) it would be if it could be like anything?!

35) Do you think we’re looking for the same things from this relationship?

36) Do you think we feel the same way about each other? Our love is equal? 

37) How healthy do you think our relationship is?

38) Do you think we have any toxic traits or habits?

39) Are there any times you think our relationship feels unbalanced? Why? And how does that make you feel?

40) I mean – who do you think wears the pants in our relationship, here?! (Click here to find out for sure!)

Difficult Questions To Ask Your Boyfriend To Test His Love

It’s time to step it up a notch with some difficult questions to ask your boyfriend to test his love.

These are mostly theoretical situations and some of them are a little “risky” so be careful about how you ask them and if you want to even ask them.

But the answers you’ll get will be pretty fascinating – that’s one thing we can say!

41) What would you do if we found out I was pregnant next month, and it was totally unplanned? (Unless you’ve been speaking about it of course!)

42) If I told you I’d cheated on my ex before (multiple times, even) would that make a difference to us and our relationship, o you think?

43) What would you do if I ever cheated on you? How would you react, and what would it mean for us? (Just make sure you say, “Don’t worry – it won’t actually ever happen!”)

44) On the flip side, how do you think I would react if you ever cheated on me?!

45) Does it matter to you, how many people that I’ve slept with before? (Be honest.)

46) Would my sexuality make a difference to you, and how you feel about me?

47) How does it make you feel, hearing about my past relationships, and thinking about me being with someone else? Does it bother you at all?

Questions To Ask Your Boyfriend To Test His Love

Here’s The Hardest Ones Yet!…

48) How am I similar and different to your ex girlfriends? And likewise, how is our relationship both similar and different? (A tough one to talk about, I know!)

49) What is one thing that I do better than anyone you’ve been with before?!

50) Do you ever compare me to other girls, or our relationship to past relationships that you’ve had? And if so (well done for being honest!), but in which ways and why?

51) What would be your first reaction if I told you I didn’t love you anymore?

52) What would you do if I said I never wanted to see you again? Or, worse still, just walked out of your life, with little to no explanation and that was it – everything was done?!

53) If you had to break up with me (for whatever reason), how would you do it?!

54) If I ended it with you, how long do you think it would take you to move on?!

55) How long do you think it would take me to move on? (See what he thinks about you!)

56) Do you think we could ever break up and things be left on bad terms with me? (Touch wood it never comes to that!)

57) If I had to move away for a few years and we had no choice but to do long distance for that time – would you stay with me? Why / why not?

58) If I gained 50 pounds, would it change the way you feel about me?

59) What if I was struggling significantly with my mental health? How much could and couldn’t you deal with?!

60) What things wouldn’t you be able to deal with me doing, or being like?

Questions To Ask Your Boyfriend To Test His Love

Woah, we’ve got through some heavy questions now, huh? We’ve stormed through to the half way mark, and we’ve got plenty more yet…

61) Which do you prefer – me in the morning or me at night?!

62) Is there anyone that I remind you of? And if so – in what ways?

63) What’s one thing you’ve never told me (or anyone perhaps for that matter) but which you would like to?

64) How well do you think we resolve conflict?

65) When we fall out, or have an argument, do you talk to others about it, or prefer for us to resolve it ourselves?

66) How much conflict do you think could be avoided? And if so, how?

67) How strong do you think the trust is in our relationship?

68) Have I ever done anything to make you question your trust, and did that influence the way that you feel about me?

69) What things would bother you in our relationship? What boundaries do you have?

70) Have I ever made you feel under-valued or disrespected in the relationship? When and how?

Remember, This Feedback Is Invaluable…

71) What do you think you could do, to make me feel more loved?

72) What could I do to make you feel happier, or more loved?

73) Do you think we both put the same amount of effort into the relationship? And if so, how?

74) Do you feel like you could talk to me if you had any concerns about the relationship? And, why / why not?

75) Are you satisfied with all of the types of intimacy that we share? (Emotional, Intellectual, Physical, etc. Run through each type of connection and discuss.)

76) Do you think that anything’s missing or lacking in our relationship?

77) Are there any things that make you feel jealous in our relationship?

78) Are there any things that make you feel insecure in our relationship?

79) How jealous / insecure / [change the word here] do you think I am, and does that influence the way that you see / feel about me?

80) Do you think our relationship could ever turn into more of a friendship? Why / why not?

Questions To Test His Love…

81) How strong do you think our friendship is, within the relationship?

82) How important do you think that friendship is in a relationship?

83) In what ways do you think we’ve changed as individuals since meeting each other?

84) In what ways do you think we haven’t changed as individuals since meeting each other?

85) Do you think we spend enough time together? Have we got the right balance in our relationship?

86) Do you think our relationship has moved forward at the right pace? Not too fast or too slow?

87) Do you / have you, ever felt pressured in our relationship?

88) Do you feel like you can still do everything you want to do in this relationship? It’s not too controlling at all?

89) What do you think of my family? (Be honest.) Do you feel like you fit in?

90) And do you feel like I get on with, and fit in well with, your family?

Let’s Keep Them Coming…

91) How do you think we positively and negatively influence each other?

92) What qualities do you think you have, that have rubbed off on me in some way?

93) What’s your happiest memory (or a few of your happiest memories) of our relationship?

94) What makes you feel the closest and most connected to me?

95) Are there ever times that you feel disconnected to me? Or like you barely even know me?

96) Do you think we have seen each other at our best and worst? And what times were these?

97) At what point did we become comfortable enough to really open up to each other? And what have been the biggest things we’ve shared, to bring us those steps closer?

98) What makes you feel like you can open up to me?

99) How have I been “your rock”? And what do you think shows that you have been, and always will be, mine?

100) What do you remember the most about the day / night we first met? (This leads me onto the last section…)

Questions To Ask Your Boyfriend To Test His Love

Questions To Ask Your Boyfriend To Test His Love

And we’re nearly there! Hasn’t this been rather “juicy”?! I hope these questions have helped to provide you with a little more clarity and confidence.

So let’s finish off with some lighter questions to ask your boyfriend to test his love. These last 20 WILL be like a quiz… but a fun one! 

Know the answers, write them down and see if yours and his match up! Ready? Set… Go, go, go!

101) When did we go on our first date? What was the day and date of it?

102) Where did we share our first kiss? And who initiated it? How did it happen?

103) When did we first get intimate and go “all the way”? And what was that like?!

104) BONUS: How has our physical intimacy changed and progressed since we first got together?

105) When and where did I first tell you I love you? And how did you respond?

106) How long did it take us to stop dating and become exclusive?

107) When and how did you ask me out? (Or vice versa.) How did we become “official”?

108) When did we then make it “Facebook official”, and how did we feel about that?

Onto The Last Ones…

109) How did we celebrate our last anniversary and when was it?

110) BONUS: How would I most like to celebrate our next significant anniversary?

111) What did my friends and family first think of you when they met you?

112) When did we first meet each others friends / family and what did we do?

113) What are three things that I love the most about you? (See how much he listens!)

114) What’s my idea of an ideal date? What would I most like to do? (See how well he knows you!)

115) What makes me feel the most loved? What’s my love language, even? (Guess each others!)

116) What’s my favourite position in the bedroom? (Then see if you know his!)

117) What’s one of the funniest things that’s happened in our relationship so far?

118) What’s the most romantic thing that I’ve done for you? And the most romantic thing you’ve done for me?

119) What’s one thing you will always treasure about our relationship?

FINAL QUESTION: 120) What should I remind myself if I’m ever doubting or wondering if you love me, and how much you love me?!

That’s All For This One

So there we have it – 120 questions to ask your boyfriend to test his love.

Remember what we said with how to go about it, and don’t forget to throw in the lighter ones at the end too!

Looking for shorter, snappier questions? Then try these 100 (Serious!) Yes or No Questions For Couples. There’s some tricky but important ones in there too!

Have confidence in yourself, your worth, and your relationship. And if you are having any major doubts – talk them through properly with your partner… not in code through a “test!”

Good luck. Wishing you all the very best. And don’t forget – I’m on hand with Relationship Coaching should you ever need.


120 Questions To Ask Your Boyfriend To Test His Love
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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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