100+ Tricky Love Questions to ask your boyfriend or girlfriend

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By: Naveen B

The questions you ask others tell more about your personality rather than the answers you receive from the person you’re asking.

If you are asking a question means, you are controlling the situation and the person you are interacting with.

In order to make that situation or conversation stand out, make sure your thought and intention are in a right place. Make use of your intuition to formulate your questions to gain respect and love.

So, if your love is in just a beginning stage and you want to make a good first impression or strengthen your connection, asking questions is the best way to continue.

Love itself is pretty philosophical and very personal to each individual.

Also read: 85 Trick questions to ask your girlfriend (and know what’s in her mind)

So, asking love questions is also a bit tricky way to understand a person. Especially, tricky love questions can test a person’s intellect and how he or she handles the scenario.

It’s good to ask trap questions to your boyfriend or girlfriend. But you should ask questions that are focused on uplifting and encouraging rather than manipulating or intentionally mean.

In this post, I have written well-thought-out trick questions to ask your boyfriend or girlfriend. Perhaps, these tricky love questions and answers guide you in getting to know your partner better.

Tricky love questions

List of tricky questions to ask your boyfriend or girlfriend.

trick questions ask your boyfriend 100+ Tricky Love Questions to ask your boyfriend or girlfriend

1. If you were a billionaire and I was a pauper, would you still love me? 

2. If your life depended on it, how much could you give up for me? 

3. If I was never a part of your life, would you still have succeeded? 

4. Can you imagine a world without me?

5. Is there anything in your past that would break us apart if I ever learned about it? 

This question is tricky because it may bring up past secrets or issues that your partner may not want to talk about.

It could also make them feel guilty or ashamed if they have something in their past that they are not proud of.

The outcome of this question could be either positive or negative, depending on how your partner responds and how you handle the information they give you.

If they are honest and open with you, it could bring you closer together and increase trust in your relationship.

However, if they are not comfortable sharing or if their past is something that is difficult for you to accept, it could cause tension and potentially harm the relationship.

6. If I had all my doubts and fears stripped away, what would they be? 

7. Do you believe there is anything in life that makes it impossible for people to stay together through thick and thin?

8. Would you rather lose everything but never see me again or never live without me but lose everything?

9. What is one reason why we can’t be together forever no matter what happens or what anyone else says?

10. What is it that you never want me to change? 

Asking this question is tricky because it can potentially bring up sensitive issues or insecurities in the relationship.

It may also make the other person feel like they are being pressured to change certain aspects of themselves.

The outcome of this question could be a positive conversation about what each person values and appreciates in the other, but it could also lead to hurt feelings or a feeling of being misunderstood.

Additionally, asking this question may also bring up areas where the other person feels like they want the other person to change, but may not feel comfortable bringing up.

It could also lead to an uncomfortable conversation about areas where the other person may want to change but is not willing to do so.

Overall, the outcome of this question depends on how it is approached and the current dynamics of the relationship.

It’s important to be open and honest with each other while also being sensitive to each other’s feelings.

11. If we were together, do you think that one day we would be arguing like we do right now? 

12. What do you like best about me but really awkward to share?

13. When I’m not around, who are you thinking about? 

14. Is our relationship a competition for your attention with everything else in your life?

15. Are there secrets between us that you don’t want me to ever find out about? 

You may think you know your partner, but asking this question can be tricky because it could open up a can of worms and lead to difficult conversations.

It can also bring up issues that your partner may not want to confront. It may make your partner feel uncomfortable or defensive.

They may feel like you don’t trust them or that you’re accusing them of hiding something.

It’s important to approach this question with care and sensitivity, and to be prepared for the possibility of an uncomfortable conversation.

The outcome of this tricky relationship question could vary depending on your partner’s response.

If they are honest and open with you, it could lead to a deeper level of trust and understanding in your relationship. However, if they are evasive or defensive, it could cause tension or mistrust.

It’s important to be prepared for any outcome and to be willing to discuss and work through any issues that may arise.

Also read: Trick questions to ask your boyfriend to get to know him better.

Tricky love questions and relationship questions to ask your boyfriend or girlfriend

16. What do you like least about me and afraid to share? 

17. How important are sex and physical intimacy to you in a relationship? 

18. If I told you that I didn’t love you anymore, what would change? 

19. Is there anyone who wants something from us as a couple that is more important than us being together?

20. When we’re having problems or arguments and things get rough, how long can you last before giving up or moving on because it’s too hard or not worth it?

In every relationship, it’s important to know how much your partner is willing to invest in it and how long they are willing to stay in it even when times get tough.

There is no right or wrong answer to this question, and it could be a tricky one to ask because it could bring up issues of commitment.

Asking this question could result in your partner opening up about their feelings towards the relationship; and could help both of you come to an understanding of how you both feel and what you are willing to do to stay together.

One thing to be aware of is that it could also lead to an argument if you don’t both have the same expectations of the relationship.

So, it’s important to ask this question in a way that conveys understanding, not judgement.

21. What are your thoughts when things aren’t going well between us but we still try harder to make it work because it could be so good if we got past these problems? 

22. If I had one day left on earth and only one thing I wanted to happen before I died, what would it be with you and why?

23. What would happen if you didn’t ever see me again? 

24. Would you be willing to wait for me if I needed more time before making a decision about us? 

25. How long do you think we could last living together day-to-day before one of us got tired of dealing with each other and it was no longer worth it or working anymore?


Also read: 33 Trick questions to ask your boyfriend to see if he loves you

26. If we were in an argument and something happened that made us both extremely angry, what would be on your mind first: breaking up or getting even with me? 

27. What are three positive things that come to mind when you think about our relationship? 

28. What are three negative things that come to mind when you think about our relationship?

29. What would be your first reaction if you knew that I had cheated on you and were caught? 

30. If our relationship was a color, what color would it be and why? 

31. If we were a celebrity couple, who would we be most like and why? 

32. What do you like about me that nobody else notices? 

33. What do you like about me that other people notice more than I do? 

34. Would you rather always have things just go your way or give up all of your control over yourself and your life in exchange for our relationship working forever without fail from here on out and through any obstacles?

35. What would you do if I told you I was no longer in love with you?

36. What would you do if I suddenly became famous and had to move away for work?

37. If I changed my appearance drastically, would you still love me the same?

38. If I had a serious accident and became disabled, would you still love and stay with me?

39. If I had a child from a previous relationship, would you be able to love and accept them as your own?

40. If I had a serious medical condition that would require constant care, would you be willing to take care of me?


41. If I had to choose between you and my family, which would I choose?

42. If I lost all my money and became financially dependent on you, would you still love me?

43. If I had to move to a different country for an extended period of time, would you wait for me?

44. If I had to make a life-changing decision that would affect our relationship, would you support me?

45. If I had to choose between you and my career, which would I choose?

46. What is the most difficult thing you have ever had to forgive in a relationship?

47. If you could go back in time, would you change any past decisions that led to our current relationship?

48. How would you react if I told you that I am considering moving away for an extended period of time?

49. How do you deal with jealousy in a relationship?

50. What is the most important thing that you would need in a relationship for it to be successful?

51. How do you define love?

52. What is the most difficult thing you have ever had to tell someone you loved?

53. If we were to have children, what would be your ideal parenting style?

54. What is the most important thing that you would need in a partner for a successful relationship?

55. What is the most difficult thing you have ever had to accept in a relationship?

56. What is the most important thing that you would need in a partner for a successful long-term relationship?

57. Do you ever compare me to other women?

58. Are there any past relationships that you still have feelings for?

59. Do you ever imagine your life without me?

60. Are you satisfied with our current level of intimacy?

61. Do you ever have thoughts of cheating on me?

62. Are you still attracted to me as much as you were when we first met?

63. Do you think about marriage and starting a family with me?

64. Are there any deal breakers for you in this relationship?

65. Do you think we have a strong enough foundation for a long-term relationship?

66. Are there any aspects of my personality that you wish I would change?

67. Are there any hidden insecurities that you have about our relationship?

68. Do you ever feel like you’re missing out on something better?

69. Are you content with the way our relationship is currently progressing?

70. Are you happy with the level of communication we have in our relationship?

71. Do you ever feel like you’re holding back in our relationship?

72. Are you completely honest with me about everything?

73. Do you think we have a healthy balance of independence and togetherness in our relationship?

74. Are you comfortable with the amount of time we spend together?

75. Are there any unspoken rules in our relationship that I should know about?

76. Do you ever have doubts about our future together?

77. Are you happy with the amount of trust we have in our relationship?

78. Are there any unresolved issues from our past that still affect our relationship?

79. Do you ever feel like you’re settling for less in our relationship?

80. Are you comfortable with the amount of vulnerability we share in our relationship?

81. Are you happy with the amount of effort we put into our relationship?

82. Are you content with the way we handle conflicts in our relationship?

83. Do you ever feel like we’re not on the same page about our relationship?

84. Are you happy with the amount of compromise we have in our relationship?

85. Are there any boundaries that you feel uncomfortable crossing in our relationship?

86. Do you ever feel like you’re sacrificing too much for our relationship?

87. Are you happy with the level of emotional support we provide for each other?

88. Are you comfortable with the amount of space and privacy we give each other in our relationship?

89. Are you happy with the amount of growth we have in our relationship?

90. Do you ever feel like we’re not compatible in our relationship?

91. Are you happy with the amount of affection we show each other in our relationship?

92. Are you comfortable with the amount of commitment we have in our relationship?

93. Are you happy with the amount of love we have in our relationship?

94. Do you ever compare me to other girls you’ve dated in the past?

96. Do you have any secret desires or fantasies that you’re not sharing with me?

97. Can you imagine a future without me in it?

98. Have you ever had feelings for someone else while we’ve been together?

95. Are you truly happy in our relationship or just settling for me?

99. Are you truly committed to our relationship or are you still keeping your options open?

100. Are you holding back any emotional or physical affection from me?

Related: 350+ Questions about love that make you think deep

Tricky love questions you shouldn’t ask (or think twice before asking)

These are some really sensible and controversial relationship questions you should be avoiding asking at any cost. Because, more than they strengthen your bond, there are chances they can backfire and ruin your relationship.

Of course, these tricky questions might reveal a lot about a person. But, why risk your relationship just to satisfy your ego or personal beliefs?

Still, if you want to give it a try and get to know your person more deeply, you should rather be careful or be mindful before asking these tricky love questions. And be prepared for the consequences in advance.


Also read: 200+ Trap Questions on different topics to ask anyone to trick them

Because if the answers won’t turn out as per your expectations, eventually you will end up hurting your feelings or other person and make the situation worse. So, are you mentally and emotionally ready? Here you go then –

1. Is it me or your family that matters the most to you?

This is indeed a tricky love question but more than that, it’s just a stupid question, to begin with.

Because this love question itself is a bit controversial and creates a negative vibration about the person who asks no matter what answer you may receive from the person you are asking.

A good and thoughtful person knows that family is the first priority no matter what. And a more self-aware partner knows that she or he is also one of the family members.

Yet, If you are asking this question means you are separating your partner from their family. And that is no good to anyone.

Therefore, a good boyfriend or girlfriend avoids asking this question just to save their bond.

2. Suppose we both were in a dangerous situation. Would you rather save yourself or me first?

This question is also very tricky but it is irrelevant and possibly will never happen. So, why ask it?

That said, unfortunately, even if it happens, of course in that situation, our very first instinct is to save ourselves. Only then we can have the opportunity to save others.

My advice to you is just practical when you are thinking about something sensible and put yourself in another person’s shoes. Instead, think about what would you do in that situation.

It depends on an individual’s risk apatite. Nonetheless, brave man or woman will risk their lives to save their loved ones.

But again, It’s a test of time. We can’t conclude anything just by assumption.

Sometimes some things will happen naturally asking this will not help even if he or she responds that I am going to save you just to make you feel better.

So, keep your curiosity about the real incident. But don’t hope that danger should happen in reality.

Why ruin your good relationship on something that will never happen. Even if it happens, time will reveal itself about a person.

Therefore, don’t worry, be happy, and embrace your bond by living in the moment. Leave the uncertainty to its fate. Eventually, everything is going to happen for good.

Also read: 150 Trap Questions to ask your girlfriend

3. If someone better than me tries to enter into your life, what would you do?

This tricky question is also a similar case as above. But it connects the past to the future and leads to a controversial outcome.

If you are asking this question means you literally want to know, will you dump me when someone better than me enters into your life?

It’s good to worry about the future but again it depends upon you how well you nurture your relationship.

Even after knowing you are a genuine person and still he or she leaves you for another person. Then they never really deserved you or loved you.

But if you are curious to know your partner’s thoughts, try asking this tricky love question just for fun.

Only if you think your partner is optimistic. And don’t take the answers to your heart.

Also read: 20 Serious questions to ask your boyfriend

4. Will you sacrifice yourself our love?

This is truly an interesting question but there is some negativity attached to it.

However, one thing we should always remember is that love itself is sacrificing. We sacrifice our time, energy, and even personal passions at times.

Some things in relationships are very painful to express in words. Sacrifice, pain, passion, and love go hand in hand.

Of course, love and relationships are built on communication, sharing, and expressing ourselves.

But sometimes, no words can match someone’s love and no external ways can prove someone’s level of love towards others.

We need to learn to understand the silences too. Giving personal space when needed and understanding individual needs for spiritual growth is the true sign of a great understanding relationship.

Which is really what we are lacking in this modern generation of love.

As you know actions speak more than words. So, keep some questions in your mind waiting for the time to reveal those situations, and help you judge your understanding of the person you are in love with.

Also read: 300 Questions to ask your boyfriend (This strategic list reveals a lot about him)

Also read: 100 Trap questions to ask your boyfriend (Persuasive and Funny)

This is a crucial question that means a lot for many people who are looking for a virgin boyfriend or girlfriend.

Asking these tricky love questions will help you know your partner’s background and past relationships so that you can estimate the status of your future relationship.

5. With how many people did you have a physical intimacy relationship with in the past?

But be careful in approaching to ask this question. If he or she is comfortable sharing their past continue otherwise avoid it.

Again, If it really matters to you about knowing their past just ask in a casual tone and let them open by themselves.

When they feel that you are an understanding person then they will reveal their secret world to you. Good luck.

Related: 125 Questions that make no sense (Very funny and creative)

100+ Philosophical questions about love with answers

250+ questions for couples to strengthen their connection.

tricky love questions 1 100+ Tricky Love Questions to ask your boyfriend or girlfriend
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Tricky love questions to ask your boyfriend


Here is the list of tricky love questions to ask your boyfriend to get to know him deeply as a person. These questions will help you get into his mind and can guide you to see and understand how he perceives the world around him.

These love questions will also connect you both if the answers will match your perceived values and morals.

Just a quick reminder. Whatever the answer you receive, try to be open and respect his perspectives. That’s more crucial in a relationship. And also remember that the answers will not stay forever.

As people grow old they become mature and their views and priorities will also change. By keeping in that mind just enjoy the conversation and focus on building authenticity and genuine connection.

1. How self-love is important in a relationship?

2. How can a person prove his love towards others?

3. Can you love a person and still stay without having sex with him/her for your lifetime?

4. What is one thing about you that you never want to share with anyone?

5. Can you own a person you love?

6. Is self-sacrificing a true love?

7. Would you prefer to love a virgin or a non-virgin?

8. How do you know if a person is your soulmate?


9. How do you communicate your love without expressing in words?

10. Can you live without loving anyone?

Related: 200+ Questions to ask a guy to get to know him better

Tricky questions to ask your boyfriend to see if he loves you


List of trick questions to ask your boyfriend:

Where do you think we both will be in the next 5 years?

This is such a direct trick question to ask your boyfriend to see if he loves you.

If he is really planning his future together with you, then he doesn’t have any choice other than giving clues or confessing directly by saying, “of course, we both get married.” or anything related that includes you both on a personal level.

From there, you can continue the conversation to get more clarity about his motives for you.

If he says something like, “I don’t know or I don’t have any idea” Or just talks about his dreams without including you in them. Then perhaps he is not taking you and your relationship that seriously.

Why do you think suddenly my school friend is flirting with me?

Asking this tricky question will make your boyfriend angry or jealous. Just pay close attention to his facial expressions or visual cues.

If he suddenly gets mad at you and shows unusual behavior, and asks you more questions, these are some signs he is really interested in you and loves you.

If not, he won’t take that as a serious matter and behaves like he is not that concerned about it.

Trick questions to ask your boyfriend to see if he’s cheating


Here are some good trick questions to ask your boyfriend to see if he’s cheating. You can also use the same trick questions to ask your girlfriend to see if she’s cheating.

Can I use your phone for a few days, mine is not working?

This trick question will give you an idea of what your boyfriend is up to. If he says sure you can use it and gives his phone with no second thought then this is one sign he is loyal to you.

But if he asks too many questions and avoids responding to you, then this is something you need to be worried about.

Although, if he is not cheating, at least there should be transparency and trust should be there in each other. Sometimes these kinds of tricky questions will help you get to know more about your boyfriend.

Who is that girl you have been calling in your dreams while sleeping?

If you and your boyfriend staying together, you can use this trick question on him.

Just see how he responds. If he panics and shows some obvious behaviors that create more doubts about him. Then you need to have clear communication with him before the situation gets worse

Tricky love questions to ask your girlfriend


Here is the list of tricky love questions to ask your girlfriend or crush (you can ask these same questions to your boyfriend as well).

However, keep the conversation fun and sportive. Then the connection will automatically build based on each other’s positive and compatible energies.

1. Who do you love the most in your life?

2. Around whom you will be your true self?

3. Can you live without talking to or seeing me for 5 years?

4. What is self-love mean to you?

5. Why love is different in reality from dreams?

6. Why do you think our paths crossed and what made us fall in love with each other?

7. How has my love influenced you as the person you aspire to become?

8. Are you in peace with me or looking for something more?

9. Do you feel that you found your person?

10. On what occasions do you feel jealous of me?

Related: 250+ questions to ask a girl to spark conversation and build a relationship.

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Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry. His expertise as a self-help and relationship Coach has been highlighted through his articles in medium and substack to name a few. To be updated with his latest work, connect with him by following his social media accounts.

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