50+ Trick Questions Ask your Boyfriend

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.

Some are random trick questions to have fun with your boyfriend and a few are a bit thoughtful questions.

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.

Also read: 31 Deep questions to ask your boyfriend (Be evolved after this conversation with him)

It’s important to know the person you are dating, so some serious relationship-building questions are in order.

Why not get them thinking about 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


Tricky questions to ask your boyfriend

List of trick questions ask your boyfriend:

1. What Do You Consider Cheating?

2. What Things Would You Consider A Betrayal Of Trust?

3. When Was The Last Time You Got A STD?

4. When Did You Lose Your Virginity? With Me Or Someone Else? 

5. Do You Ever Wonder How Different Our Lives Would Be If We Had Never Met? 

6. Has Anyone Ever Told You That They Loved You Before I Did? 

7. Are There Any People In Your Life That I Need To Know About?

8. Do You Think I’m Beautiful? 

9. Do You Think We’re Moving Too Fast? 

10. What Would You Do If I Cheated On You? 

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

12. What Can I Do To Make You Love Me More? 

13. Are We In A Relationship Or Just Friends? 

14. Have You Ever Told Anyone That They’re The One For You Before Me? 

15. Do You Want To Break Up With Me, But Are Afraid Of How I’ll React? 

16. Would It Upset You If I Started Dating Someone Else? Or Would It Drive You Crazy? 

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

18. Do you think luck is a factor in life? Why or why not? What makes a person lucky and what do they have to do with it?

19. Are men and women really that different or are there just expectations placed on them by a society that create these differences of opinion between them?

20. Who is one person who, if they asked you a question, you would answer honestly even if it may hurt their feelings or offend them?

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


Trick questions to ask your partner regarding relationships

The following are few more tricky questions to ask your partner:

1. If I met your friends without telling you, what do you expect to happen?

2. What do you think I would do if I found out you were keeping something from me?

3. Would you choose your career over our relationship?

4. How do you feel about your exes? Do you consider being friends with them?

5. Would you be okay with me having a close friendship with an ex?

6. Have you ever been in a situation where you were tempted to cheat?

7. Have you ever felt like you settled for me instead of choosing me wholeheartedly?

8. How many people have you slept with before me?

9. Do you think your family and friends like me, or have they expressed any negative opinions about me?

10. Have you ever had any secrets you’ve kept from me that you think would upset me?

11. Have you ever had doubts about our relationship or considered breaking up with me?

12. Have you ever told your friends something negative about me that you wouldn’t say to my face?

13. What’s the biggest lie you’ve ever told in a relationship?

14. Have you ever had feelings for one of my friends?

15. Have you ever compared me to your ex?


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

Here are list of trick questions to ask your boyfriend to see if he loves you:

1. Am I your first choice? Or are there a couple of other girls you would have preferred over me?

If he hesitates in answering or doesn’t give you a straight yes, it means that he is aware of some traits about you that bothered him initially and he has taken time to get past them.

Don’t be too upset if he says no because it might just mean that they are still working on their relationship with you as well.

2. Do you love my face or body? If he says that he loves your mind and soul first, it means that looks are not important to him.

But if he says that your looks are his main criteria for falling in love with you, then it could be time for a serious talk about how much you value yourself.

And how much importance you put on physical appearance. Don’t get upset if he says he likes both – we all want some eye candy.

This question is about prioritizing physical attributes over others, so let him tell you exactly what’s more important.

3. Does it matter to you whether I am a virgin or not? If he says that he doesn’t care about your past, it’s a good sign – some people like knowing that their partner is as untouched as possible.

If he says that having sex with him will be his first time too, then there could be some problems in your relationship already if he hasn’t had any relationships yet.

Of course, if he lies about it and pretends like you are his first, then don’t trust him.

Just because someone has had one sexual partner doesn’t mean they aren’t trustworthy – but if it bothers him enough to lie about it from day one, then you should have doubts as well.

4. Are we in a committed relationship or just casual Friends with benefits?

If he says that you are both only friends and there is no commitment, then don’t bother trying to get into his pants or have him start treating you better – he is not interested in dating you.

If he says that you are only friends, but it could turn into something more, then go ahead and pursue it.

If he treats you like his girlfriend but tells you that he isn’t ready for a serious relationship yet (usually after being together for months or even years), don’t let him manipulate you into thinking that it’s all your fault.

Just because they don’t have time right now doesn’t mean it’s your problem – so move on.

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

5. What would you do if someone better than me, enters your life? This question is so important because it reveals how much he values himself and his principles over everything else.

In fact, it shows that he is aware of what a commitment means and its value in building a strong relationship.

But if he says that he wouldn’t hesitate to break up with you even if it was just for one night, then run.

This will not end well and should serve as an immediate red flag that he doesn’t know what love really means – which can be dangerous. Don’t ignore it.

6. If I tell you that I like something about another person more than what I like about you, how will you react?

This is a bit of a trick question to ask your boyfriend because it’s difficult to answer – no one likes being told they’re not good enough and might end up getting defensive. 

But instead of saying, Oh, he/she is nothing compared to you.

He needs to think through why he thinks that person isn’t good enough for him or just say he doesn’t want to see them with anyone else ever again.

Be careful if he says that it doesn’t bother him or says anything like Yeah, but I still love you.

It means that he isn’t willing to put in as much effort as necessary into making sure your relationship stays healthy and strong.

7. Do you love me as much as I love you? If he says yes, then it means that he is aware of how important your feelings are and that he has no problem being honest with them – which is a great thing.

But if he says no, then why are you here? It means that he has many issues that need to be addressed in order for him to treat his partner well – such as lack of awareness, low self-esteem, or just plain jealousy.

No one should ever say they don’t love their significant other more than they love themselves because it doesn’t make sense – unless, of course, you don’t value yourself at all.

Find out why he feels that way before making any decisions about your relationship.

8. Do you respect my opinions and wishes or always think about yourself? This question is a test of how much he respects you and your feelings – what’s more important, his desires or yours?

Because if he is willing to put your needs above his own, then it’s a good sign that he might be able to offer you a healthy relationship.

But if he says I don’t really care what you think because I do whatever I want all the time, then don’t waste any more time on him – no one should have control over your thoughts and feelings.

Also read: 50 Relationship questions to ask your boyfriend (Deep & serious topics)

9. Would you spend time with your friends, even if I tell you not to? If he says “Yes, I will listen to you as per the situation.”

That means he doesn’t want to upset you and will make an effort to avoid certain situations – which is great because it shows that he wants what’s best for both of you.

But if he says No, then understand the situation and go with your intuition.

10. If I get jealous at some point and say no/do something bad, how would you react?

This is a very important question because it tests his honesty and ability to remain calm in order to avoid arguments as well as his willingness to compromise when things go wrong – which are two essential ingredients for any healthy relationship.

He should always respect your feelings, even if he doesn’t agree with them, and understand that you can both make mistakes; if he doesn’t realize that then run.

No one should ever tell their partner not to be upset – it only shows that they don’t care about their needs or are trying too hard to change them which is never good.

11. Would you mind if I invite my guy friends to our home? If he says Yes, that means he is accepting of your right to be independent and hang out with whomever you want.

But if he says no, then just like with question 10: no one should ever tell their partner not to be upset – it only shows that they don’t care about their needs or are trying too hard to change them which is never good.

They should always understand that making new friends doesn’t mean betraying old ones – unless, of course, your ex-boyfriend was a lifelong friend who suddenly became an ex after meeting a girl from work at a party.

But hopefully, you have already talked about why exes should stay away from each other before getting into a relationship.

Also read: 20 Serious questions to ask your boyfriend


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

List of trick questions to ask your boyfriend to see if he’s cheating:

1. Is everything okay between us? You never know what’s going on in someone else’s mind, but sometimes a seemingly simple yes doesn’t really tell you much of anything.

If you really need to figure out whether or not there’s trouble brewing behind closed doors, ask straight out if everything is okay with him and his feelings toward you.

2. Why haven’t we had sex regularly these days? Your partner should be more than willing to share why he’s not showing interest in sex again—if only because avoiding such questions is one sign of infidelity.

3. Who is that girl you have been calling in your dreams while sleeping? If he says it’s not you, then run.

That doesn’t mean he wants another girl but it does show a lack of respect for your feelings and emotions which can become much more detrimental if left ignored.

However, if he says You are such a great person and I love everything about you including all of your flaws then trust him and give him every chance to prove it by not showing any disappointment whatsoever.

After all, any guy who admits his faults as well as appreciates yours has nothing to hide or be afraid of – so don’t start putting yourself down by playing mind games with him because there’s no point!

4. Can I use your phone for 2-3 days please? It’s very possible that there isn’t any meaning behind your partner using the phone secretly.

But since cell phones are basically personal data holders these days it may hold clues to who he talks to regularly and what type of messages pass back and forth between two people close enough to text each other frequently (or privately).

5. When did our pets start acting weird around you? It may seem strange for cats and dogs to pick up on your partner’s behavior before you do.

They just sense changes in behavior differently than humans—but maybe they’ve picked up on something different about him that gives them a reason to avoid him now more than ever before.

6. Are you being honest with me about where you were last night?

Recalling an unfinished discussion from earlier in the day, whether it was a disagreement or a conversation that didn’t go anywhere, can help you gauge if your guy is hiding something from you.

Just be sure to choose a time that you both remember clearly to avoid accusations of selective memory.

7. Have you started to trust me less? You may not know exactly what’s going on with your partner.

But if you ask him point blank if he trusts you, he won’t be able to lie—even if there’s a serious problem in your relationship that might make it hard for him to trust anyone.

8. What’s up with not having sex anymore?

It can be pretty embarrassing to bring up a lack of sexual activity in your relationship, but once you do, it might get him talking about his feelings and worries.

And no matter what issues he brings up, reassure him that you care for him and aren’t bothered by his needs or desires.

9. Why haven’t you called me for days? There are times when life gets in the way of daily contact with friends and family members, especially if they live far away from one another.

But if it happens more often than not, then maybe there’s more going on than meets the eye.

10. Why have things become so impersonal between us? If something is bothering a guy, he’ll usually hold it in until it explodes and becomes too much for him to bear.

So if you’re noticing that he’s distancing himself from you lately, you need to confront him about it before things get out of hand.

When people stop being honest with their feelings because they think that no one cares or no one will do anything about them anyway, they can end up resenting their partner instead of confronting them.

If he’s truly done caring about your relationship and is just going through the motions (which could lead to marriage), then you might as well find out now instead of later.

11. If I tell you that I like something about another person more than what I like about you, how will you react?

This is a bit of a trick question because it’s difficult to answer – no one likes being told they’re not good enough and might end up getting defensive.

But instead of saying Oh he/she is nothing compared to you.

He needs to think through why he thinks that person isn’t good enough for him or just say he doesn’t want to see them with anyone else ever again.

Be careful if he says that it doesn’t bother him or says anything like Yeah, but I still love you.

It means that he isn’t willing to put in as much effort as necessary into making sure your relationship stays healthy and strong.

12.Can’t a man just have feelings for another woman without having an affair or cheating on his wife or girlfriend in any way at all?

For example, can’t he talk about another girl because he admires her hair, even though it’s nothing more than admiration and is certainly not a sexual attraction?

If that’s possible and allowable, why do you feel it’s not okay for him to admire your friends’ good qualities if they are attractive women too?

When he looks at other women and feels flattered that someone finds him attractive (even if there is no sexual aspect involved).

How does that threaten you or make you feel insecure compared with how he feels when you look around and feel flattered by what others think of you as well?

While people may sometimes cross over certain lines of propriety, whether intentionally or unintentionally, I’d like him to be able to answer that one truthfully before we get serious.

13. How much longer do you want to play these games?

The main idea behind asking a guy why he wants to play these games with you is that if he has no intention of committing, then he’s wasting your time and should make his feelings known by either breaking up with you or being honest about his intentions.

After all, there is nothing fun about dragging out an almost-relationship for months on end when it’s abundantly clear that neither of you sees it going anywhere.

It gets frustrating and exhausting trying to be someone’s second best when in reality, that person has already given their heart away to another.

Before giving up on him completely, I would at least like him to try being upfront with me so I don’t have anything hanging over my head every time we see each other.

14. Your actions don’t match your words; which one am I supposed to believe ? A relationship that is going to last has to be based on trust, honesty and respect – if any of those elements are missing, it’s doomed from the start.

If a guy is saying all of these wonderful things but his actions are saying something completely different, there has got to be a reason for it – he might not have even realized he was doing it or has no desire at all to change it.

The bottom line is, love means giving each other your time, effort and affection without expecting anything in return.

When someone doesn’t do that anymore or takes those three things away from you altogether , then they aren’t really loving you in any real sense of what that word means.

15. Why are we spending so much time apart lately? If he’s going out and doing things with his friends but not including you, it means that his priorities have changed.

It can be difficult for a couple to stay close after a while if they’re both busy with school, work, and their own interests – especially if their partner is not supportive of them.

Someone who cares about you wants to spend as much time with you as possible without feeling like they’re being smothered or overwhelmed by your company.

In fact, he should want to share even more of himself because he trusts that you won’t make fun of him or judge him for it.

Someone who genuinely loves you should have no problem putting extra effort into remaining close and keeping things exciting.

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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 medium and substack to name a few.

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