150 Trick Questions to Ask Your Boyfriend & What They Reveal About Him

These trick questions to ask your boyfriend are perfect for sparking interesting discussions and enjoying playful date nights together.

These aren’t about tricking him into confessing he’s cheating you or anything along those lines. It’s all for lighthearted fun and getting to know each other on a deeper level.

Expect to discover new things about one another, share giggles, and create unforgettable memories!

Trick Questions to Ask Your Boyfriend

Ask your boyfriend these trick questions and have a good laugh as he maneuvers around them. 

It’s a fun way to see how your priorities and values align in a light and breezy manner!

1. If you could choose to go anywhere in the world with anyone, who would it be?If you could choose to go anywhere in the world with anyone, who would it be?
2. If I tell you to jump, would you ask how high or why?If I tell you to jump, would you ask how high or why?
3. What would you save first if our house was on fire: me, the dog, or your gaming console?What would you save first if our house was on fire: me, the dog, or your gaming console?
4. Would you rather fight one horse-sized duck or 100 duck-sized horses?Would you rather fight one horse-sized duck or 100 duck-sized horses?

5. If you could date any celebrity, who would it be?If you could date any celebrity, who would it be?
6. Would you still love me if I turned into a worm?Would you still love me if I turned into a worm?
7. What would you do if you woke up one day as a girl?What would you do if you woke up one day as a girl?
8. If I asked you to stop seeing your best friend, would you?If I asked you to stop seeing your best friend, would you?
9. Would you rather always tell the truth and hurt me or lie to protect me?Would you rather always tell the truth and hurt me or lie to protect me?
10. If you would receive $10,000 to spend in one day, what would you buy?If you would receive $10,000 to spend in one day, what would you buy?

11. Do you think I'm more like a cat or a dog?Do you think I'm more like a cat or a dog?
12. If you could erase one memory from your life, what would it be?If you could erase one memory from your life, what would it be?
13. What's the one thing you'd change about me if you could?What's the one thing you'd change about me if you could?

14. Would you rather be rich and single or poor but with me?Would you rather be rich and single or poor but with me?
15. If you could relive any day with me, what day would it be and why?If you could relive any day with me, what day would it be and why?
16. If you had to pick a new name for me, what would it be?If you had to pick a new name for me, what would it be?
17. What’s one secret you’ve never told me?What’s one secret you’ve never told me?
18. If you could read my mind for a day, would you? Why or why not?If you could read my mind for a day, would you? Why or why not?
19. Would you rather have me be completely honest with you or always make you feel good about yourself?Would you rather have me be completely honest with you or always make you feel good about yourself?
20. If I had an identical twin, how would you know it's really me?If I had an identical twin, how would you know it's really me?

21. If you could live anywhere in the world but without me, would you do it?If you could live anywhere in the world but without me, would you do it?
22. If I turned into a zombie, would you keep me or kill me?If I turned into a zombie, would you keep me or kill me?
23. If you could change one thing about your past, what would it be?If you could change one thing about your past, what would it be?
24. If you could be rich and famous but forever alone, would you take it?If you could be rich and famous but forever alone, would you take it?
25. Would you rather know the date of your death or the cause of your death?Would you rather know the date of your death or the cause of your death?
26. If you had to describe me in one word, what would it be?If you had to describe me in one word, what would it be?
27. If I were a color, which one would I be and why?If I were a color, which one would I be and why?
28. Would you rather forget me or forget everything else in your life?Would you rather forget me or forget everything else in your life?
29. If you could swap lives with anyone for a day, who would it be and why?If you could swap lives with anyone for a day, who would it be and why?
30. Would you rather have more time or more money?Would you rather have more time or more money?

These questions can spark interesting and revealing conversations, but remember to ask them in a playful and loving manner to keep the mood light and fun. 

The “trick” parts of these questions reveal a lot about his priorities, empathy, loyalty, and how he handles complex or ethical dilemmas. 

By gauging his responses, you can gain insights into his personality, how he perceives your relationship, and what he values most in life. 

So, get ready for some enlightening and potentially amusing answers!

Trick Questions to Ask Your Boyfriend to See If He Loves You

Playful and thought-provoking relationship questions are a fun way to see just how many heart-shaped balloons float around in his head when he thinks of you.

Here are some clever, light-hearted questions designed to subtly (or not so subtly) reveal his true feelings and show just how much he’s into you.

1. If you had to choose between winning the lottery or having me by your side forever, which would you choose? (Like having you by his side wasn’t winning the lottery, duhh.)If you had to choose between winning the lottery or having me by your side forever, which would you choose? (Like having you by his side wasn’t winning the lottery, duhh.)
2. If you could swap your life with anyone for a day, would you choose me?If you could swap your life with anyone for a day, would you choose me?
3. Would you rather be with me in a tiny home or alone in a mansion?Would you rather be with me in a tiny home or alone in a mansion?
4. If you were given a magic lamp with three wishes, what would your first wish be?If you were given a magic lamp with three wishes, what would your first wish be?
5. If you could go back in time to when we first met, would you still choose to be with me?If you could go back in time to when we first met, would you still choose to be with me?
6. Would you rather know all my thoughts or always have me know yours?Would you rather know all my thoughts or always have me know yours?
7. If you could give up one of your hobbies to spend more time with me, would you?If you could give up one of your hobbies to spend more time with me, would you?
8. If we were in a scary movie, do you think you would save me first or yourself?If we were in a scary movie, do you think you would save me first or yourself?
9. If you had to describe your perfect day, would I be in it?If you had to describe your perfect day, would I be in it?
10. If you could change one thing about our relationship, what would it be?If you could change one thing about our relationship, what would it be?
11. Would you rather go on a pain-in-the-neck hike with me or an all-inclusive vacation alone?Would you rather go on a pain-in-the-neck hike with me or an all-inclusive vacation alone?

12. If we were both astronauts on a mission to Mars and could only communicate through one message a day, what would your first message to me say? (Send noods?)If we were both astronauts on a mission to Mars and could only communicate through one message a day, what would your first message to me say? (Send noods?)
13. If you had to pick between never watching your favorite movie again or spending every evening with me, what would you choose?If you had to pick between never watching your favorite movie again or spending every evening with me, what would you choose?
14. If you could be an animal, which one would you be and why?If you could be an animal, which one would you be and why?
15. If you had to live one day over and over again, which day would it be?If you had to live one day over and over again, which day would it be?
16. Would you rather live without your phone or without me?Would you rather live without your phone or without me?
17. If you could write a book about our love story, what would the title be?If you could write a book about our love story, what would the title be?
18. If you had to pick between your dream job and staying in the same city as me, which would you choose?If you had to pick between your dream job and staying in the same city as me, which would you choose?
19. Would you rather be able to see into the future or change the past, and why?Would you rather be able to see into the future or change the past, and why?
20. If you could choose any superpower to help our relationship, what would it be? (Being Henry Cavil-level hot qualifies as a superpower, right?)If you could choose any superpower to help our relationship, what would it be? (Being Henry Cavil-level hot qualifies as a superpower, right?)

21. Would you rather always win an argument or never argue at all? (Trick: There’s no winning in arguments.)Would you rather always win an argument or never argue at all? (Trick: There’s no winning in arguments.)
22. If you could make one promise to me that you could never break, what would it be?If you could make one promise to me that you could never break, what would it be?
23. If we could only communicate through one word for a day, what word would you choose?If we could only communicate through one word for a day, what word would you choose?
24. If I could grant you one wish right now, what would it be?If I could grant you one wish right now, what would it be?
25. If you had to choose between always telling me the truth or always making me happy, what would you pick?If you had to choose between always telling me the truth or always making me happy, what would you pick?
26. If you could be famous but it meant you had to leave me behind, would you do it?If you could be famous but it meant you had to leave me behind, would you do it?
27. Would you rather have all your wishes granted or grant all of mine?Would you rather have all your wishes granted or grant all of mine?
28. If you could erase one thing about your past, what would it be?If you could erase one thing about your past, what would it be?
29. Would you rather live a long life without me or a short life with me?Would you rather live a long life without me or a short life with me?
30. If you had to choose between forgetting our first kiss or our last conversation, which would it be?If you had to choose between forgetting our first kiss or our last conversation, which would it be?

These questions are designed to shine a light on his thoughts, motivations, and feelings in a cheeky, engaging way. The devil is in the detail — it’s all about seeing where you fall on his list of priorities. And here’s a spoiler: Being number one isn’t always the goal. After all, being on a pedestal only stays fun for so long.

The tricky bits will show you his true priorities, empathy, loyalty, and how he handles tough situations. His answers will give you a deeper understanding of his personality, your relationship, and what he values.

So, get ready for some eye-opening and (im)possibly entertaining revelations!

Funny Trick Questions to Ask Your Boyfriend

Injecting a bit of humor into your relationship can bring you closer and create lasting memories. 

Here are some funny, tricky questions to ask your boyfriend that will not only make him laugh but also keep the conversation lively and entertaining.

1. If you had to be a vegetable, which one would you be and why?If you had to be a vegetable, which one would you be and why?
2. Would you rather fight a chicken every time you get in your car or a monkey once a year?Would you rather fight a chicken every time you get in your car or a monkey once a year?
3. If you were a cartoon character, who would you be?If you were a cartoon character, who would you be?
4. If you had to choose between always having to sing instead of speaking or dance everywhere you go, which would it be?If you had to choose between always having to sing instead of speaking or dance everywhere you go, which would it be?
5. Would you rather have a pet dinosaur or a pet dragon?Would you rather have a pet dinosaur or a pet dragon?
6. If you could only eat one food for the rest of your life, what would it be?If you could only eat one food for the rest of your life, what would it be?
7. If you could swap places with any animal for a day, which would it be?If you could swap places with any animal for a day, which would it be?

8. Would you rather have spaghetti for hair or maple syrup for sweat?Would you rather have spaghetti for hair or maple syrup for sweat?
9. If you had to pick one superhero to be your roommate, who would it be and why?If you had to pick one superhero to be your roommate, who would it be and why?
10. Would you rather always have to wear clown shoes or a clown wig?Would you rather always have to wear clown shoes or a clown wig?
11. Would you rather always have to whisper or always have to shout?Would you rather always have to whisper or always have to shout?
12. If you could be a character in any movie, who would you be?If you could be a character in any movie, who would you be?
13. Would you rather your life have a rewind button or a pause button?Would you rather your life have a rewind button or a pause button?
14. If you could be invisible for a day, what would you do?If you could be invisible for a day, what would you do?
15. Would you rather have a third arm or a third leg?Would you rather have a third arm or a third leg?
16. If you could only use one word for the rest of your life, what word would it be?If you could only use one word for the rest of your life, what word would it be?
17. Would you rather be a giant hamster or a tiny rhino?Would you rather be a giant hamster or a tiny rhino?
18. If you could turn any object in your house into a robot, what would it be?If you could turn any object in your house into a robot, what would it be?
19. Would you rather always have to hop on one foot or always have to squawk like a chicken?Would you rather always have to hop on one foot or always have to squawk like a chicken?
20. If you could have any fictional character as your best friend, who would it be?If you could have any fictional character as your best friend, who would it be?

21. Would you rather have to always wear wet socks or a wet shirt?Would you rather have to always wear wet socks or a wet shirt?
22. If you could swap places with any celebrity for a day, who would it be and why?If you could swap places with any celebrity for a day, who would it be and why?
23. Would you rather always have to speak in rhymes or have to rap everything you say?Would you rather always have to speak in rhymes or have to rap everything you say?
24. If you could only watch one movie for the rest of your life, what would it be?If you could only watch one movie for the rest of your life, what would it be?
25. Would you rather have the ability to fly but only at 1 mph or run at 100 mph but only for 10 minutes at a time?Would you rather have the ability to fly but only at 1 mph or run at 100 mph but only for 10 minutes at a time?
26. If you had to have an animal noise as your alarm clock sound, what would it be?If you had to have an animal noise as your alarm clock sound, what would it be?
27. Would you rather be a wizard or a superhero?Would you rather be a wizard or a superhero?
28. If you could only eat breakfast foods or dinner foods for the rest of your life, which would you choose?If you could only eat breakfast foods or dinner foods for the rest of your life, which would you choose?
29. Would you rather have to wear a tuxedo every day or pajamas every day?Would you rather have to wear a tuxedo every day or pajamas every day?
30. If you had to live in a TV show or movie for a month, which would it be?If you had to live in a TV show or movie for a month, which would it be?

Flirty Trick Questions to Ask Your Boyfriend

Adding a touch of flirtation to your conversations can spice up your relationship and keep things exciting. 

Here are some flirty trick questions to ask your boyfriend that will tease and charm him, while also revealing his playful side.

1. If you could give me a new nickname based on my personality, what would it be?If you could give me a new nickname based on my personality, what would it be?
2. Would you rather have a romantic picnic in the park or a cozy dinner at home with me?Would you rather have a romantic picnic in the park or a cozy dinner at home with me?
3. If you could pick one song to dance with me to right now, what would it be?If you could pick one song to dance with me to right now, what would it be?
4. Would you rather have a date night where we dress up fancy or a casual date in comfy clothes?Would you rather have a date night where we dress up fancy or a casual date in comfy clothes?
5. If you could read my mind for a day, what do you think you'd find out?If you could read my mind for a day, what do you think you'd find out?
6. Would you rather take a moonlit walk on the beach with me or go stargazing in the mountains?Would you rather take a moonlit walk on the beach with me or go stargazing in the mountains?
7. If we could teleport anywhere for our next kiss, where would it be?If we could teleport anywhere for our next kiss, where would it be?
8. Would you rather receive a handwritten love letter from me or a surprise kiss?Would you rather receive a handwritten love letter from me or a surprise kiss?
9. If we could time travel to any era for a romantic date, which era would you choose?If we could time travel to any era for a romantic date, which era would you choose?
10. Would you rather spend a rainy day cuddling inside with me or playing in the rain together?Would you rather spend a rainy day cuddling inside with me or playing in the rain together?
11. If you could choose one movie scene to reenact with me, which one would it be?If you could choose one movie scene to reenact with me, which one would it be?

12. Would you rather me serenade you with a love song or dance with you under the stars?Would you rather me serenade you with a love song or dance with you under the stars?
13. If we could write our own love story, how would it begin?If we could write our own love story, how would it begin?
14. Would you rather have me whisper sweet things in your ear or surprise you with little love notes?Would you rather have me whisper sweet things in your ear or surprise you with little love notes?
15. If you could plan a surprise date for us, what would you do?If you could plan a surprise date for us, what would you do?
16. Would you rather kiss me in the rain or hug me in the snow?Would you rather kiss me in the rain or hug me in the snow?
17. If you could create a special holiday just for us, what would it be called and how would we celebrate it?If you could create a special holiday just for us, what would it be called and how would we celebrate it?
18. Would you rather receive a romantic poem written by me or a scrapbook of our memories?Would you rather receive a romantic poem written by me or a scrapbook of our memories?
19. If we could spend a day in each other's bodies, what's the first thing you would do?If we could spend a day in each other's bodies, what's the first thing you would do?
20. Would you rather always hold my hand or always have your arm around me?Would you rather always hold my hand or always have your arm around me?
21. If you could design a dream date just for us, what would it involve?If you could design a dream date just for us, what would it involve?
22. Would you rather have a romantic getaway in a cozy cabin or a luxurious hotel?Would you rather have a romantic getaway in a cozy cabin or a luxurious hotel?
23. If you could surprise me with a gift right now, what would it be?If you could surprise me with a gift right now, what would it be?
24. Would you rather wake up to breakfast in bed made by me or a morning cuddle session?Would you rather wake up to breakfast in bed made by me or a morning cuddle session?
25. If you could spend an entire day doing anything with me, what would you choose?If you could spend an entire day doing anything with me, what would you choose?
26. Would you rather have a spontaneous dance party with me or a quiet night under the stars?Would you rather have a spontaneous dance party with me or a quiet night under the stars?
27. If you could create a playlist for us, what would the first three songs be?If you could create a playlist for us, what would the first three songs be?
28. Would you rather have a surprise romantic evening planned by me or plan a surprise for me?Would you rather have a surprise romantic evening planned by me or plan a surprise for me?
29. If we could recreate any moment from our relationship, which one would it be and why?If we could recreate any moment from our relationship, which one would it be and why?
30. Would you rather have a candlelit dinner with me or a playful night of board games and snacks?Would you rather have a candlelit dinner with me or a playful night of board games and snacks?

Deep Trick Questions to Ask Your Boyfriend

Delving into deeper conversations can strengthen the bond and understanding between you and your boyfriend. 

Here are some deep trick questions designed to provoke thought and reveal more about his inner feelings and perspectives.

1. If you could keep one thing about our relationship constant, what would it be?If you could keep one thing about our relationship constant, what would it be?
2. Would you rather have a life full of adventure but uncertainty, or a predictable but peaceful life?Would you rather have a life full of adventure but uncertainty, or a predictable but peaceful life?
3. If you could ask me any question and be guaranteed a truthful answer, what would it be?If you could ask me any question and be guaranteed a truthful answer, what would it be?
4. If you had to choose between always making me happy but never feeling happy yourself, or always being happy but never making me happy, what would you choose?If you had to choose between always making me happy but never feeling happy yourself, or always being happy but never making me happy, what would you choose?
5. Would you rather forget all our past memories together but stay with me, or remember everything but never see me again?Would you rather forget all our past memories together but stay with me, or remember everything but never see me again?
6. If you could see into the future, what would you want to know about us?If you could see into the future, what would you want to know about us?
7. If we could solve one problem in the world together, what would it be and why?If we could solve one problem in the world together, what would it be and why?
8. If you could describe our relationship in one word, what would it be and why?If you could describe our relationship in one word, what would it be and why?
9. If you could take away one of my fears, what would it be and why?If you could take away one of my fears, what would it be and why?
10. Would you rather have the power to change one decision in your past or control one decision in your future?Would you rather have the power to change one decision in your past or control one decision in your future?

11. Would you rather be able to read my mind or have me read yours?Would you rather be able to read my mind or have me read yours?
12. If you could relive one moment in our relationship, what would it be and why?If you could relive one moment in our relationship, what would it be and why?
13. If you had to choose between a fulfilling career or a happy relationship with me, which would you choose?If you had to choose between a fulfilling career or a happy relationship with me, which would you choose?
14. Would you rather face all your challenges alone or have me face them all for you?Would you rather face all your challenges alone or have me face them all for you?
15. If we could move anywhere in the world together, where would it be and why?If we could move anywhere in the world together, where would it be and why?
16. If you could fix one mistake you've made in our relationship, what would it be?If you could fix one mistake you've made in our relationship, what would it be?
17. Would you rather have a lifetime of wealth but be lonely, or have just enough to get by but be surrounded by loved ones?Would you rather have a lifetime of wealth but be lonely, or have just enough to get by but be surrounded by loved ones?
18. If you could choose one lesson you've learned from our relationship, what would it be?If you could choose one lesson you've learned from our relationship, what would it be?
19. Would you rather always be able to make me laugh or always be able to comfort me when I cry?Would you rather always be able to make me laugh or always be able to comfort me when I cry?
20. If you could write a letter to your younger self about our relationship, what would you say?If you could write a letter to your younger self about our relationship, what would you say?

21. Would you rather have the ability to see every place we will go together or every emotion we will feel together?Would you rather have the ability to see every place we will go together or every emotion we will feel together?
22. If you could know one thing about my future, what would it be?If you could know one thing about my future, what would it be?
23. Would you rather live a long life without ever falling in love, or a short life with your soul mate?Would you rather live a long life without ever falling in love, or a short life with your soul mate?
24. If you could change one thing about the way we communicate, what would it be?If you could change one thing about the way we communicate, what would it be?
25. Would you rather have all your dreams come true but lose me, or never have any of your dreams come true but stay with me?Would you rather have all your dreams come true but lose me, or never have any of your dreams come true but stay with me?
26. If you could learn one thing from me, what would it be and why?If you could learn one thing from me, what would it be and why?
27. Would you rather always know the truth, even if it hurts, or live in blissful ignorance?Would you rather always know the truth, even if it hurts, or live in blissful ignorance?
28. If we could only achieve one goal together, what would it be?If we could only achieve one goal together, what would it be?
29. Would you rather experience all the highs and lows of life with me or have a smooth but unexciting life?Would you rather experience all the highs and lows of life with me or have a smooth but unexciting life?

These questions are perfect for sparking deep, meaningful conversations with your boyfriend.

They’re crafted to unveil his true thoughts and feelings about your relationship in a fun, relaxed way. 

The trickier bits will give you a peek into his values, priorities, and future dreams. By his answers, you’ll get a better sense of his inner world, how he views your relationship, and what truly matters to him. 

So, sit back, relax, and get ready for some enlightening and touching chats that’ll bring you two even closer together!

Conclusion

These trick questions are a fun and engaging way to interact with your boyfriend. 

Whether you’re looking to spark interesting discussions, enjoy playful moments, or see how well he knows you, these questions are sure to provide plenty of entertainment and insights into your relationship.

If you want to read more topics about being in a relationship, check out our page here.

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