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

You know your boyfriend better than anyone – or at least you should by now. But sometimes, even the most trustful and committed relationships can be tested.

Maybe you have been dating for a long time, maybe you have just moved in together, or maybe your relationship has hit a rough patch.

Sometimes in life, you might wonder if your significant other truly loves you or not. While it’s easy to tell when someone doesn’t love you, it can be very difficult to tell when they do.

If you want to get to know your boyfriend better, then you can ask him some deep questions about his life, values, and beliefs.

These tricky love questions can be used as a fun way to pass the time when you are alone together.

Or they can be used as part of a game which helps to take the pressure off having to come up with a great question yourself.

But there are also some trick questions that can help to reveal if your boyfriend really is telling the truth or not.

Here are some set of trick questions to ask your boyfriend to see if he loves you.

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

tricky questions to ask your boyfriend to see if he loves you 33 Trick questions to ask your boyfriend to see if he loves you

1. What would you do if I cheated on you? It is a bit of a morbid tricky question to ask in general, but especially if your relationship is going well. Hopefully, this question will never be relevant.

But if it does come up then you might want to know what his reaction would be before it happens. It is better to ask this question at the beginning of a relationship before things get too serious.

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While his answer may not be the ideal answer, it will still give you an idea of what his underlying values are when it comes to loyalty and respect within a romantic relationship.

2. If I got pregnant tonight, what would you do? Again, his answer would reveal how serious he is about the relationship — but also about whether he’s thinking in the long term.

If he talks about marriage and kids down the road. This one is a great question for seeing how much he cares about kids. Even if both people want kids, there’s still a huge difference between someone who wants them and someone who’s ready.

If he says he’d be on board immediately, then it means that his feelings are genuine and real. But if he admits to being unsure… well then there’s room for doubt. After all, how can you fully commit yourself to something without being sure about it first? That answer will tell you a lot.

 3. Would it matter to you whether Am I virgin or not? It’s sad that we have to bring up sexual history on a list like this, but hey, love is hard sometimes!

But if he says no, then his true feelings for you might be more than just physical. After all, who wants to make love with someone who doesn’t care about such an important topic? But if he says yes. Well then again, there’s room for doubt.

4. Do you ever compare me to other girls? It’s not too much of a trick question, but it’s still going to make him think carefully about his answer before he gives it.

This is going to make him stop and consider what he has said in the past whenever he might have compared you to other women.

5. What is your favorite part of my body? Some guys have something specific that they like about every girl they date or even see.

If there is something in particular that he likes about your body, this is an easy way to get him to tell you what it is without asking him directly.

6. How would you describe me to someone who doesn’t know me?

This is a bit tricky because we all have our faults so he might mention more than one thing here. 

He might also say that you are funny or that you have a great smile which is always nice to hear! But if he starts listing off what’s wrong with you then it’s probably time for some soul searching.

7. Would you give up all your money for me? If your boyfriend says yes, that means that he loves you more than money and material things.

This is a big deal for some guys because they are so used to having those things in their life. Be prepared that he might say no if he puts money on the same level as love or higher.

8. How do you feel about getting married? This is a tricky question that will leave your boyfriend speechless unless he has been thinking about proposing to you.

This is the perfect question if you think he is getting ready to pop the big question, but it may make him nervous if he is not ready.

9. Are we ready to be parents? This one might be a little tricky, but it is one of the good trick questions to ask your boyfriend. Based on his answer alone, you can already decipher if he is really serious with you or not.

If he says “yes”, then that means he is ready to settle down with you and have kids. However, if he says “no” then that means he is not yet ready for such a commitment and relationship.

10. Have you been checking someone else out recently? This tricky question will reveal his level of honesty and trustworthiness. 

If he tells the truth, that is great but if not, then maybe it’s time to re-evaluate whether the relationship is worth saving. Either way, This tricky question will help you find out if he has eyes for anyone but you.

Pretend it doesn’t bother you, regardless of what his answer is, and act like it doesn’t faze you one bit! It’s all about the game!

Also read: 75+ Tricky love questions to ask your boyfriend

11. What are the things in my life that make you jealous? This question will help you know what makes him insecure about himself or about his relationship with you. You should then avoid those things to have a peaceful relationship.

12. Which do you prefer – me in the morning or at night? This tricky question will help you understand his opinion on physical appearance and outer beauty. The answer will reveal how much he values your relationship and what he wants from it.

13. If I had to move far away for many years, would you wait for me? This is a tricky question, but it is a great way to find out what he thinks about commitment and long-distance relationships.

14. When you think of me, what memory comes to mind? This will show whether he always remembers the best times with you or if it’s something else that is most important to him.

15. What would be your first reaction if I told you that I don’t love you anymore? This question tells you how important your relationship is for him.

16. If I told you that I have cheated on my ex, would that make a difference between us? His answer will let you know whether he can forgive infidelity or not and what he thinks of cheating in general.

17. If we had a fight, would you call your friends to discuss it or try to sort things out with me? This question lets you know whether he considers your relationship as something serious and whether he is mature enough to handle the private life.

18. What would you do if I said I never wanted to see you again? The answer to this question may reveal a lot more than what it seems.

If he says he’d be devastated, or try and change your mind then it’s pretty obvious that he’s in love with you. But if he says he’d shrug and move on. Well, then it’s another discussion.

19. How do I compare with all of your ex-girlfriends? This is one of those tricky questions that might sound harsh, but it’s not. The answer to it can be very telling.

If he says you’re better than any ex (which is a good thing!) then again, it’s pretty obvious that he’s in love with you. But if he admits to having found a flaw, well, then there’s room for doubt.

20. Where do you see us in 10 years’ time? This one is one of my favorite trick questions to ask your boyfriend to see if he loves you because it can reveal so much about where your relationship might go.

If he doesn’t see himself with you in 10 years’ time, then he probably isn’t that into you – sorry! But if his plans for the future include you, then it could be a sign that he sees a long-term relationship with you.

Also read: 50 Trick or trap questions to ask your boyfriend

21. What do you think of my family? This question might make your boyfriend feel like he has to be careful with his words.

If your family really does not get along with him and nothing anyone does can change their mind, then this could lead to an argument.

What is important is what he thinks of your family, not what they think of him. It also gives you a chance to talk about how much he loves you and your family and why.

22. Do you think I can trust my best friend? This is another question that might make your boyfriend uncomfortable.

He might feel like he has to choose between two people that he loves or two people that are very important in his life.

If you ask this question, try not to get offended if he says no; it simply means that he does not think she is trustworthy, but it does not necessarily mean that he thinks she would hurt you on purpose.

23. Do you want kids, if so how many would you prefer? Not everyone wants children, so this question could reveal important information about the potential of your relationship.

If one of you wants kids and the other does not, then that might mean you two are not a good match.

24. What would happen if I died? This is one of those hard but important questions that we need to ask in our lives.

Here, you are going to be asking him whether or not he will be sad and will miss you when something bad happens. If his feelings for you are true, then there’s a good chance that his answer will be yes.

25. Who do I remind you of? This question will tell us how much he knows about our family, friends and other people in general.

We might not all have the same views on who reminds us of whom but it’s still interesting! And maybe even a little scary. 

A good way to avoid this is by asking them directly: “Do I remind any celebrities?”

26. How would you describe me in one word? This question will make your boyfriend think carefully about how he would answer it.

If he finds himself saying that you are beautiful, cute, intelligent or gorgeous, then it shows that he really does love you.

Some men might try to get out of answering this by saying something less obvious like “amazing” or “unique” but you want something a bit more personal than that.

You want him to say something that he would not normally say about someone else so it shows that he cares about you and only you.

27. Would you ever dump me over text? Even though you might not expect this, there are plenty of girls out there who have been dumped over a simple text message.

By asking this question, your boyfriend is forced to look at the possibility that you two could someday break up and also how it would happen

 Hopefully, he will never want to hurt you in such a terrible way and if he doesn’t answer that way, then it could be a good sign for your relationship.

Also read: 20+ Serious questions to ask your boyfriend

28. Do you think we’ll get married? It can be scary for some people to admit that they want to marry someone or even just casually date them for the long term.

Asking this question and getting an honest answer could help determine if your relationship is going anywhere.

29. Have you ever had feelings for one of my friends? This question is an interesting but a trap question, one that will take some guts to answer honestly.

You might not like the answer to this question, but it is one that is good to know. You may not have even realized that he liked one of your friends, but now you will know which one and how long he liked her for.

30. Do you think I’m smarter than other girls? This question will tell you a lot about how much he respects and values your intelligence.

The answer will also show how much he cares about your feelings and how well he knows what makes you tick — which are all essential for any healthy relationship.

31. What is the one thing that I do better than all of your ex-girlfriends? This is a serious question and not a question to be asked if you want to start a fight. It’s just a way of knowing what makes you special and better than other girls.

32. Would you let me wear anything I wanted to even if it looked bad on me? This question can reveal more than just how much he values your personal style and tastes – it can also show how good of a friend he is.

If he says no, then it means that his feelings for you might be stronger than they are. After all, who in their right mind would deny someone they love something like that… even if it was what made them look ridiculous? 

But if he says yes, well then again, there’s room for doubt. Of course, he’ll say yes; but does that mean his reasoning isn’t selfish in some way?

Maybe deep down inside, you know there’s something else going on. It’s hard to say without asking another question or two but use your intuition here.

Also read: 50+ Relationship questions to ask your boyfriend

33. If I gained 50 pounds, would it change how you feel about me? This is a question that can reveal a lot about his true feelings for you.

If he says no, then it means that his love for you is unconditional – something that isn’t going to change over time even if things aren’t going well.

Final thoughts:

It’s always good to challenge the relationship, test new boundaries, and include a few surprises here and there because that’s what keeps the relationship fresh and exciting.

These 33 questions are bound to keep your boyfriend dealing and guessing. And as you can read in the title, it really helps to know if he actually loves you or not.

Regardless of the fact that you are having trouble telling if he loves you or not, it is important to remember that love between two people is a powerful emotion. It can cause how people act, how they think, and their decisions. Love changes people.

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Author
Naveen Bommakanti

Naveen is Experienced Psychology and philosophy Writer, self-help and relationship Coach and thought influencer. He has 7 years of experience in Personal development industry.

Naveen’s expertise as a self-help and relationship Coach has been highlighted through his articles in thoughtcatalog, themindsjournal, elephantjournal, power of positivity, medium, substack and marc and angel to name a few.

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