If you’re looking to make your relationship better and stronger then this list of trick questions to ask your boyfriend will help you out with that endeavor. What makes these questions so good is that they are not only fun but also very insightful about your boyfriend and his inner world.
I have taken the time to create this list of the best possible trick questions you can ask your boyfriend to see if he loves you. Whether it be a serious relationship or just starting out and testing the waters these questions will give you some insight into how your boyfriend thinks and feels about himself and life in general.
It’s important to know the person you are dating, so some serious relationship building questions are in order. Why not get them thinking with these tricky questions? If you have been asking the same old questions, and you want to spice things up,
Here are 50 Trick questions ask your boyfriend to see if he loves you or cheating on you. These tricky questions for boyfriend will keep him on his toes and might make him wonder why you asked them.
Recommended reading: 25 Tricky love questions to ask your boyfriend
50 Trick questions ask your boyfriend to see if he loves you or cheating.
1. Have you ever lied to me? If so, why? Knowing whether or not your boyfriend has ever lied to you will give a good insight into their character and what they think of honesty.
This is a test for trustworthiness and it’s important that they are someone who values honesty and integrity in themselves as well as their significant other.
It can also uncover potential trust issues with themselves. Whether it was simply a white lie or an elaborate story, asking how often he lies will help reveal an untrustworthy person with deceptive intentions who isn’t worth having in a relationship (or most likely any relationship at all).
2. What do I need to change about myself for us to be together? This is one of the best trick questions to ask your boyfriend to test his love and see if they’re willing to accept you and all of your flaws, or if they just want someone better than you in their life.
If they expect perfection out of you, maybe it’s time you reconsider being with them if they won’t allow any room for error when it comes to being a better person.
3. Where are we going with our relationship? A lot of people don’t think about where they would like their relationships to go because they’re so caught up in their current situations and relationships.
So, it’s important that you have a future plan if you do want things to continue beyond wherever they are now. This will help determine if they value being in a long-term commitment as much as you do or if they just want to spend time with whoever is available at any given moment.
It will also show how serious he is about pursuing a future together and figuring out whether or not marriage and children fit into his grand plan for life. And don’t worry, it doesn’t mean you’re trying too hard, it just means you know what you want for yourself down the road.
4. Who is your closest friend? This might sound a little odd, but it could reveal some good information about who he is as a person and what types of people he spends his time with.
If his best friend is someone you can’t stand and they don’t seem that close, maybe he’s hanging out with him more often than you because they have similar interests and values.
This will help give you a better idea of whether or not you want to keep spending time with him if you’re worried about how much time they’ll end up taking from your relationship if they become such great friends on top of having romantic feelings for each other.
5. What do I mean to you? Do I mean more than just s#x? This is one more list of trick questions to ask your boyfriend to see if he loves you. Knowing how he views and values you as a person and his intentions for being in a relationship with you will help determine whether or not he’s genuine about his feelings for you.
This question can show if he truly wants to be with you or if he thinks of only having sex when it’s convenient for him (or vice versa).
Regardless of what type of answers come out, it’s important that he realizes how much time and effort goes into any relationship if things are going to work out in a positive way, even from one night stands.
6. Do you love me? If so, how much and how can you prove it? It might seem like a silly question at first because it’s pretty straightforward; however, it’s important to know exactly what level of commitment he wants from you as well as his feelings about commitment in general.
Some people are capable of loving others without necessarily needing a deep connection between two people in order for them to love their significant other; others will only be able to feel committed once they have that extra dose of intimacy and trust in their relationship.
Knowing where he stands on relationships will give you an idea of whether or not he’s looking for an I’ll call you relationship or something more serious because nobody likes playing games when they’re trying to find someone worth being with long-term.
7. What’s the last time you thought of me? This will show if he’s been thinking about you since it happened or if he forgot about you a long time ago and is just trying to keep up appearances so that you don’t move on.
Because obviously, no one wants someone who can’t stay loyal even after being cheated on. Plus, if he does admit that it was within 24 hours, then great! You might not need to worry about finding out how committed he is because it sounds like his feelings for you are very strong.
However, it could also be a bad sign if he can’t remember doing something nice for you in order to make sure that his relationship with you stays fresh in his mind.
Also read: 20 Serious questions to ask your boyfriend
8. How do you know you’re in love? How is that different from just liking someone or being attracted to them physically? You should want more than just sex and a crush if you’re going to be in a long-term relationship.
Therefore, it’s important that he realizes what he wants from his relationship before making any other decisions about how he wants his future relationships to play out.
9. How often do you lie? This is a very important question that might seem harsh but it’s essential if you want to get to know someone better and build a strong foundation for your relationship.
If he can’t handle answering honestly about why he lies, then there’s really no point in continuing forward because he won’t be able to be honest about anything else in order for things to work out in a positive way.
Relationships are built on trust and honesty; therefore, revealing his true feelings behind his actions will help you determine whether or not he’s someone worth getting emotionally invested into as well as physically attracted to.
10. What do you like about me? This question might seem superficial but it’s extremely important because he might not have enough of a reason beyond physical attraction and/or sexual chemistry to be with you.
Everyone needs more than just that in order for things to work out positively, even in casual relationships.
Therefore, hearing his side of things will help determine whether or not he’s worth taking seriously or if you should continue on looking for someone who is willing to put more effort into making a relationship work.
11. How many partners have you slept with? If he’s not willing to tell you, then that could mean one of two things: either he’s embarrassed about his number or he doesn’t feel secure enough in your relationship in order for him to admit it.
Because everyone has their own preferences when it comes to how many people they want their partner to be with before jumping into a long-term commitment.
Therefore, his unwillingness might just show that he doesn’t want a serious relationship and is only trying to keep up appearances so that you don’t move on from him. If he is willing to tell you, then great.
12. Have you ever cheated on someone? This is a very important question that shouldn’t be taken lightly because it can reveal some extremely valuable information about him and his past.
Everyone has done something in their past that they regret; however, he needs to realize what he did wrong so that he doesn’t repeat his mistakes and hurt you in any way. If you’re going to be serious with someone, then you want them to take things seriously as well.
Therefore, knowing how honest he is about his relationships with other people will show whether or not he has potential of being faithful or if you need to move on and find someone who isn’t willing to share those secrets with you due to embarrassment, shame, or insecurity.
13. What do you like best about me? This is definitely one of the trick questions ask your boyfriend, which will show whether or not he really cares about you and respects your opinions/ideas or if he’s only with you for sexual pleasure and nothing else.
If he can’t say anything good about you, then why would he choose to be with someone who doesn’t feel at least somewhat special in his eyes? You should want a man who loves everything about what makes you, YOU.
Therefore, hearing his side of things will help determine whether or not he’s worth taking seriously.
Also read: 120+ Questions that make no sense.
14. What do you friends think of me? If he’s embarrassed about answering, then it might be a sign that he doesn’t have any good things to say about you. On the other hand, if he’s proud to answer, then that should show how much faith he has in your relationship.
15. How do we make each other feel? This is a great question that shows how much he cares about you and not just himself. It will help you two learn more about each other while showing that he wants to hear what you have to say and care about how it makes you feel.
The last thing you want is a man who doesn’t care whether or not you’re feeling happy in your relationship.
Tricky questions to ask your boyfriend
16. Do I turn you on se#ually? This is an important question that everyone should ask their partner from time to time because it will reveal how much they’re into you and if there’s a need for improvement in any area of your relationship.
Everyone has their own preferences when it comes to what turns them on; therefore, hearing his side of things will help determine his perspectives about physical attraction.
17. Why do we argue so much? This is a great question that requires some serious honesty and communication between both parties involved so that they can figure out why arguing is such a common thing in their relationship and work toward resolving those issues before they become too big of problems.
18. How can I be a better partner? This is a question that will reveal whether or not he wants to make things work in your relationship and if he’s willing to put some effort into making it worth being in.
You should want someone who is open and honest about how they feel so that you two can make improvements on any problem areas as they come up.
19. Do you ever regret being with me? This is a question that will show whether or not he’s happy in your relationship and if he wishes things were different. Then you should have an open communication to figure it out.
20. Are we more than just lovers? This is a great question that helps you two figure out how much he respects and cares about you! When someone feels comfortable enough with you to call you his girlfriend or his wife. It’’s a sign that he really loves and respects you in return.
21. Would our family and friends approve of us being together? This is another great question that will help reveal whether or not he’s serious about your relationship because whether he likes it or not, there are certain people who have influence over how we think and feel.
22. What’s our future together? This is a great question that will show whether or not he has any idea of what he wants out of life and whether or not you fit into his picture.
23. What would you do if you became immortal tomorrow? This is a good question that will reveal whether or not he has any aspirations for himself.
Anyone can sit around and complain about things being hard or how they want different things; however, everyone should have a vision of what they want their life to look like and where they’re going so that they can work toward getting there.
Also read: 150+ Questions that are hard to answer
24. Would you rather have $1 million dollars right now or 1 penny doubled every day for 31 days? This is a great question that reveals whether or not he has a positive attitude about life and whether or not he’s worth taking seriously.
Anyone can sit around and complain about how bad things are, but anyone who takes action toward changing their life is someone who will work hard to get what they want out of life.
25. Is there anything that I do that annoys you? We all have irritating habits that might be driving our significant others crazy without them realizing it. This is a great question because if he loves you, then he’ll tell you.
In return, hear his side of things and thank him for helping with things; therefore, if something’s bugging him too bad, then figure out how to work on getting rid of it.
26. Can you tell me two things I don’t know about you? This is a great question that will help you and him feel closer! If he really loves and respects you, then there are certain secrets he wants to keep close because they have meaning in his life.
27. What are my strengths as a girlfriend/wife? Anyone in any relationship should be able to answer and one that will reveal whether or not he has faith in your abilities.
28. Are you willing to start over if things get bad between us? This question shows whether or not someone is willing to work through their problems with you.
29. If money wasn’t an issue what would you be doing right now? This is such a question that will show whether or not he has any passion for life! Everyone has passions and dreams; however, if he doesn’t have any passions then there are other things in his life that will make him happy (or one day will).
30. Would you prefer being really ugly but really rich or really good looking but poor? This is a great question that reveals whether or not he has respect for himself.
If he’s really good looking then there’s no sense in trying to work through anything with him because he doesn’t value himself.
31. Do you feel that life is short and precious? This is a great question that will reveal whether or not he truly realizes how lucky we are.
If someone can truly grasp how special life is, then they should try their best to make it last by loving and respecting their significant other.
However, if someone doesn’t care about their future, then there’s no point in trying to make things work with them.
32.What do you believe happens when we die? This is a great question that will reveal whether or not he takes life seriously.
A man who doesn’t care about his life will have a very different answer than someone who cares about his future.
33. Are you okay with how things are going right now in our relationship? This is a great question that reveals whether or not he wants more out of life and if he wants more out of you.
If he answers no, then figure out what he’s looking for and work hard to make it happen; however, if there isn’t anything missing from your relationship, then chances are there isn’t anything wrong with it either so don’t fix something that isn’t broken.
34. What’s your definition of perfect? This is a great question that will reveal whether or not he has very high standards! If he has super high standards, then chances are they are impossible to reach.
Also read: 500 Questions that make you think
35. Do you think that men and women should have different jobs? This is a great question that will reveal whether or not he values equality in life! If he answers yes, then it’s time for him to go because no one wants someone who doesn’t respect them as equals.
Trick questions to ask your boyfriend to see if he’s cheating or loves you.
36. What are three ways I can show you I love you more than anyone else could? This is a great question that will help improve communication in any relationship!.
If he can answer without hesitation, then it means he knows how much he loves you; however, if his answers are slow or nonexistent, then there are some things missing from your relationship so don’t give up on making it better.
37. How many kids do we want? This is a great question that will help determine whether or not he’s ready for a family.
There’s no use in trying to fix things if he isn’t willing to change or take responsibility for them; however, if he is open and willing, then it’s time for you both to start working towards making his dream come true.
38.What did you want when you were younger and what do you want now that you’re older? This is a great question that will help determine whether or not he’s changed for better or worse.
If he still has many of his childhood dreams, then there’s no use in trying to make them happen; however, if he has changed for the better, then you should try making some of those dreams come true because they might be more realistic than you think.
39. What kind of parent do I need to be in order for my child(ren) to be successful in life? This is one of the great tricky questions to ask your boyfriend that will help determine whether or not he’s ready for parenthood.
If he has a solid plan, then it’s time to start thinking about having kids; however, if his answers are slow or nonexistent, then there are some things missing from your relationship so don’t give up on making it better.
40. What do you think are some of the best ways people have found love in one another? This question will help determine whether or not he’s interested in falling for someone.
If he has no desire for romance, then there’s no use wasting your time on him; however, if he does want it and has ideas on how to find it, then give him a chance because maybe you both can make his dreams come true.
41. Are people important in life or can we do fine with just me and you? This is also one of the best tricky questions ask your boyfriend that will reveal whether or not he values relationships with others.
Having a close-knit relationship with family, friends, coworkers, etc., isn’t something to be ashamed of; however, if he believes everything is fine as long as he has you, then it’s time to work on it.
42. What did you love doing when you were younger and what do you like doing now that are different? This tricky question will help determine whether or not his wants have changed throughout his lifetime.
If they haven’t changed much, then maybe it’s time for him to move on; however, if they have changed significantly throughout his lifetime (for better or worse), then give him a chance because maybe there are still dreams worth pursuing.
43. What was your relationship with your father like? This is a great question that will help you determine whether or not he respects his parents.
If he still has great relationships with them, then it’s time for you both to sit down and work out any issues before moving forward.
However, if he doesn’t respect them and isn’t willing to try improving things, then there are some things missing from your relationship so don’t give up on making it better.
44. What have you always wanted but never received? This is one of the tricky questions to ask your boyfriend which will guide you whether or not he has his own problems he needs to work on.
If he doesn’t want anything, then there’s no use trying to fix what isn’t broken; however, if he does want something and isn’t willing or able to make it happen himself, then there are some things missing from your relationship so don’t give up on making it better.
45. What do you think are some of your best features? This question will help determine whether or not he has self-esteem.
If he doesn’t have much self-confidence, then it’s time for him to start building it up! However, if he does have lots of confidence, then give him a chance because maybe there are still dreams worth pursuing.
46. How do you show love to others? This is a great question that will help determine whether or not he knows how to show his affections towards other people.
If he has no idea what love means, then there’s no use trying to fix what isn’t broken; however, if he understands what love means and uses it in his daily life, then give him a chance because maybe there are still dreams worth pursuing.
47. How often do you talk about me with your family? This is one of the questions to ask your boyfriend to trick him about how much support he gets from his loved ones.
Having close relationships with parents and siblings can be very helpful when it comes to things like dating, so if he doesn’t have these relationships but wants them, then give him time to build them up.
However, if he doesn’t want them (for whatever reason), then there may be something missing from your relationship so don’t give up on making it better.
48. Have you ever thought of leaving me? This is one of the best trick questions to ask your boyfriend to see if he is cheating. And will let you know just how sure he is about being committed to you.
No one should feel threatened by another person wanting space or freedom to pursue other interests and activities.
If he thinks about leaving every once in awhile or on a regular basis, then give him time to work out any issues before moving forward. However, if he says yes all too often, then there are some serious problems going on between you two so don’t give up on making it better.
Also read: Best get to know you questions to ask a guy
49. Who are the 10 people in your social media that text you very often? Why? This is one more in the list of trick questions to ask your boyfriend to see if he’s cheating. And also that will tell you who are his friends and why they are important to him.
Family members are typically very important in someone’s life and having those bonds can make or break many aspects of a person’s lifestyle.
However, if most of his friends are girls and trying to flirt with him and if he’s responsive to them. Then there’s something wrong with your current situation.
50. Have you ever shared my photos to any another girl or guy? This is a great question that will reveal whether or not he’s honest with you! If he’s honest, then there’s no use trying to fix what isn’t broken; however, if he lies, then give him time to work out any issues before moving forward.