109 Trick Questions Ask your Boyfriend

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By: Naveen B

Are you ready to put your boyfriend’s brain to the test and have some fun while doing it? Considering trick questions to ask your boyfriend are the perfect way to add a little spice to your relationship.

From love to romantic and serious to funny and random, try these trick questions ask your boyfriend. Tricky love questions will keep him on his toes and have him thinking for a while. You might even learn a thing or two about each other in the process.

For example, do you want to know if your boyfriend is being serious about your relationship? Ask him, What would you do if I told you I no longer want to be exclusive? Or, if you want to test if he’s jealous or open to polygamy relationship, ask him, How would you feel if I start a friends with benefits relationship with an ex?

But don’t worry, we’ve got plenty of fun and lighthearted questions too. Want to stump him with a silly question? Try asking, “What would you do if I asked you to wear a wedding dress to our next date?”

And if you’re looking for some deep and meaningful conversation, we’ve got you covered with questions like, “Do You Ever Wonder How Different Our Lives Would Be If We Had Never Met?” or “Are There Any People In Your Life That I Need To Know About??”

So, grab a drink, cuddle up with your boyfriend, and get ready to these 109 trick questions to ask your boyfriend. Who knows, you might just learn something new about the love of your life!

What are trick questions and why you should ask them to your boyfriend?

Trick questions are questions designed to catch someone off-guard or to challenge their assumptions. They often involve a play on words or a hidden meaning.

Asking tricky questions to your boyfriend can be a fun way to challenge his thinking, spark interesting conversations, and get to know him better.

There are many reasons why you might want to consider trick questions to ask your boyfriend.

For one, they can help you gauge his intelligence and critical thinking skills.

They can also reveal his sense of humor and his ability to think on his feet.

Additionally, tricky questions can be a fun and lighthearted way to break the ice or spice up your conversations.

Also read: 70 Funny trap questions to ask your boyfriend

Advantages and benefits of asking tricky questions to boyfriend

Asking tricky questions to your boyfriend can have many advantages, including:

1. Building a deeper connection: Asking thought-provoking questions can help you learn more about your boyfriend’s thoughts, feelings, and values, which can help you build a deeper emotional connection.

2. Improving communication: By asking tricky questions, you’re encouraging your boyfriend to open up and share his opinions and ideas, which can improve communication between you.

3. Strengthening trust: Asking difficult questions shows that you trust your boyfriend enough to listen to his answers and not judge him for his thoughts or opinions.

4. Enhancing intimacy: Sharing personal thoughts and feelings can enhance intimacy between you and your boyfriend.

5. Discovering shared interests: Asking tricky questions can help you discover shared interests and hobbies, which can strengthen your bond.

6. Learning about each other’s pasts: Tricky questions can help you learn about your boyfriend’s past experiences and how they’ve shaped him into the person he is today.

7. Having fun: Tricky questions can be a fun and playful way to get to know each other better and share a laugh.

8. Developing problem-solving skills: Asking tricky questions can help you and your boyfriend develop problem-solving skills by thinking critically about hypothetical situations.

9. Improving empathy: By asking questions that require your boyfriend to put himself in someone else’s shoes, you can help him improve his empathy and understanding of others.

10. Strengthening the relationship: Overall, asking tricky questions can strengthen your relationship by promoting open communication, mutual understanding, and shared experiences.

Just be mindful of your partner’s boundaries and make sure to respect them if they don’t feel comfortable answering a certain question. Asking tricky questions should be a fun and rewarding experience for both of you.

Also read: 150+ Questions to ask your boyfriend to test his love, if he cares, if he is serious about you or still wants to be with you

Tips to ask trick questions to your boyfriend

1. Keep it light and fun: Tricky questions should be playful and entertaining, not confrontational or accusatory.

2. Be creative: Try to come up with unique and unexpected questions that will surprise and challenge your boyfriend.

3. Don’t be too obvious: Tricky questions should be subtle and clever, not overly obvious or contrived.

4. Use humor: Humor can help defuse any tension or discomfort that might arise from a tricky question.

5. Be prepared for unexpected answers: Tricky questions can elicit surprising and unexpected responses, so be ready to roll with the punches.

It’s important to be careful when asking trick questions to your partner. Some questions may be too personal or sensitive, and may lead to arguments or hurt feelings.

You need to approach trick questions with an open mind and be prepared to listen to your partner’s answers without judgment.

Recommended reading: 100 Tricky love questions to ask your boyfriend

Here are 100+ 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.

100+ Tricky Questions to ask your boyfriend (love and relationships)

The following is a list of love and relationship trick questions ask your boyfriend:

1. Do you think it’s okay to keep secrets from each other?

This is a tricky question, as it depends on your individual relationship dynamics. Some couples feel that it’s okay to keep certain things to themselves, while others would prefer complete transparency.

This tricky question can help you understand how your boyfriend views trust and communication in a relationship. It can also help you determine how open he is to sharing certain personal information with you. 

2. How would you feel if I bought myself a gift without consulting you?

Some men love when their partner is independent and doesn’t need to consult them on every decision. Others may feel a bit slighted that they weren’t asked to be part of the decision. 

3. What would you do if I didn’t answer your calls or texts for a day?

This question is an important one to ask if you’re in a serious relationship as it could reveal how your partner might react in a stressful situation.

4. What would you do if I asked you to do something you’re uncomfortable with?

If your man values your opinion, he should be willing to compromise. Asking this question will show you whether your partner respects your wishes or if he’s more of a take charge kind of guy. 

5. How would you feel if I start a friends with benefits with an ex?

This can be a sensitive topic as it can bring up trust issues. It’s important to make sure your partner is comfortable with the idea before proceeding. 

6. What would you do if I told you I wanted to take a break?

This is a difficult situation for any couple to be in, so it’s important to know how your partner would handle it. It could also reveal a lot about how he values the relationship. 

7. What would you do if I told you I no longer want to be exclusive?

This is another difficult topic that needs to be discussed frankly. It’s important to make sure both partners are on the same page when it comes to their expectations.

8. Do you think we should inform each other if we’re in the presence of someone we’ve slept with?

This is a tricky question as it could reveal a lot about your partner’s trust level. It’s important to make sure both of you are comfortable with the level of information you’re sharing with each other.

9. Do you think it’s okay to flirt with other people in front of me?

This question is a great way to test your man’s boundaries and find out if he’s comfortable with you flirting with other people when you’re together.

10. What type of relationship would you prefer if you were single?

This question can give you an insight into what your partner may want from a relationship if he was single. It can also reveal a lot about how he views relationships in general.

Also read: 50 Funny trick questions to ask your boyfriend, girlfriend, friends with answers

11. Do you think it’s important to express yourself in a relationship?

Not all couples are comfortable with expressing their emotions to each other. This question can give you an insight into how your partner feels about communication in a relationship. 

12. What would you do if I told you I wanted to take things to the next level?

This is a great question to ask if you’re both considering getting serious and want to make sure you’re on the same page. 

13. Do you think it’s important to show affection in public?

This question can help you determine how comfortable your partner is with public displays of affection. It can also help you gauge if he’s willing to be affectionate with you in public. 

14. What would you do if I asked you to do something you didn’t want to do?

This is an important question to ask as it can reveal how your partner deals with disagreements. It can also help you determine how much compromise he’s willing to make in order to make the relationship work.

15. How would you feel if I asked for more alone time?

This is a tricky question as it can reveal a lot about how your partner feels about spending time with you. It can also show you whether he’s comfortable with you needing space and time to yourself.

16. What would you do if I asked you to break up?

This is a difficult topic to bring up, but it’s important to know how your partner would handle a difficult situation like this. It can also show you whether he would be willing to work things out or if he’d rather just end the relationship.

17. Do you think it’s important to discuss finances in a relationship?

This question can give you an insight into how your partner feels about discussing money. It’s important to make sure both of you are comfortable with the level of communication and transparency when it comes to finances.

18. Do you think it’s important to make time for each other?

This is an important question to ask as it can reveal how your partner values quality time together. It can also show you whether he’s willing to make an effort to spend time with you or if he’d rather just do his own thing.

19. Do you think it’s okay to have friends of the opposite sex?

This is a tricky question as it can reveal a lot about how your partner views trust and communication in a relationship. It can also show you whether he’s comfortable with you having close friends of the opposite sex. 

20. How would you feel if I asked you to move in with me?

This is a big decision that should not be taken lightly. It’s important to make sure both of you are comfortable with the idea before taking the plunge.

Also read: 100 Funny Trick Questions and answers ( Tricky riddles edition for fun)

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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? 

Also read: 100 Dirty questions to ask your boyfriend to make him laugh

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)

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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?

Also read: 100 Flirty questions to ask your boyfriend

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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

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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.

Also read: 100+ Hard questions to ask your boyfriend on different topics

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.

Also read: 250 Questions to ask your boyfriend over text (freaky, deep, funny, juicy, dirty, awkward)

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.

Also read: 150+ Questions to ask your boyfriend to test his love, if he cares, if he is serious about you or still wants to be with you

Random trick questions to ask your boyfriend

Here are some some random tricky questions to ask your boyfriend:

1. What do you call a boomerang that doesn’t come back?

2. If you had to choose between a million dollars or a lifetime supply of your favorite food, what would you pick?

3. What do you get when you cross a snowman and a shark?

4. If you could have any superpower, but it had to be completely useless, what would you choose?

5. What do you call a word that is spelled incorrectly in the dictionary?

6. If you could be any animal for a day, but had to live in the wild, what animal would you choose?

7. What do you get when you cross a turtle and a porcupine?

8. If you could have any job in the world, but it had to be one that no one else wanted, what job would you choose?

9. What do you call a song that gets stuck in your head?

10. If you could live in any era of history, but had to give up all modern conveniences, which era would you choose?

Also read: 100+ Romantic questions to ask your boyfriend

Funny Trick questions to ask your boyfriend

Here are some hilarious and funny trick questions to ask your boyfriend:

1. What would you do if I asked you to walk around the block wearing a chicken costume?

2. Do you think it’s okay to have a pet llama in the house?

3. What would you do if I asked you to wear a wedding dress to our next date?

4. How would you react if I told you I wanted to take a road trip to the moon?

5. Do you think it’s okay to have a pet elephant in the house?

6. What would you do if I asked you to give a speech in front of a crowd of strangers?

7. How would you feel if I told you I wanted to start a band and asked you to be the lead singer?

8. Do you think it’s okay to wear matching outfits on our next date?

9. What would you do if I asked you to dress up like a superhero?

10. How would you react if I told you I wanted to take a hot air balloon ride around the world?

11. Do you think it’s okay to have a pet kangaroo in the house?

12. What would you do if I asked you to give a speech in front of a crowd of cats?

13. How would you feel if I told you I wanted to buy an island and asked you to move in with me?

14. Do you think it’s okay to have a pet giraffe in the house?

15. What would you do if I asked you to take part in a competitive eating contest?

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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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