350 Questions to Ask Your Boyfriend

Whether you are a new item or a seasoned couple, asking the right questions can deepen your bond, bringing you closer emotionally and physically.

I am about to serve you a cocktail of fun, serious, romantic, and downright weird questions to ask your boyfriend.

Table of Contents

Get ready to shake things up!

Spicy Questions to Ask Your Boyfriend

If you could only touch one part of my body for the rest of the night, which would it be and why? If you could only touch one part of my body for the rest of the night, which would it be and why?
If you had to describe our chemistry in one word, what would it be and why? If you had to describe our chemistry in one word, what would it be and why?
What is the naughtiest thought you have ever had about me while we were out in public? What is the naughtiest thought you have ever had about me while we were out in public?
What is the most recurring spicy dream you have? What is the most recurring spicy dream you have?
What do you think my ultimate turn-on is? What do you think my ultimate turn-on is?
What’s the sexiest memory you have of us together? What’s the sexiest memory you have of us together?
If you were to blindfold me and take control, what would you do first? If you were to blindfold me and take control, what would you do first?
What's a spicy text message you'd love to receive from me during the day? What's a spicy text message you'd love to receive from me during the day?
What’s your favorite way for me to show you affection that’s not physical? What’s your favorite way for me to show you affection that’s not physical?
What's the most surprising thing that turns you on about me? What's the most surprising thing that turns you on about me?

These questions are a perfect way to spice things up or reignite heat in a long-term relationship.

Imagine finding out he’s got a thing for head massages, or he’s been dreaming about a moonlit beach rendezvous with you toute nue.

It’s time to get playful and daring — if you don’t ask, you’ll never know!

Deep Questions to Ask Him

If you could relive one day of your life, which would it be and why? If you could relive one day of your life, which would it be and why?
What is a book or movie that profoundly changed your perspective? What is a book or movie that profoundly changed your perspective?
How do you handle failure or setbacks, and what have they taught you? How do you handle failure or setbacks, and what have they taught you?
How do you define success for yourself? How do you define success for yourself?
What is your greatest fear in life? What is your greatest fear in life?
How do you define love, and has that definition changed over time? How do you define love, and has that definition changed over time?
If you could spend an entire day doing anything you want, what would you do? If you could spend an entire day doing anything you want, what would you do?
What’s one piece of advice you would give to your younger self? What’s one piece of advice you would give to your younger self?
What is the greatest lesson life has taught you so far? What is the greatest lesson life has taught you so far?

Asking deep questions can help you truly understand him as a person, sparking profound conversations that strengthen your emotional intimacy.

Deeply personal questions about fears and life-altering influences can reveal whether your core values and beliefs are compatible.

For instance, if his idea of success is having lots of money in the bank while yours is being rich in life experiences, better to find out sooner than later. These questions can help you determine compatibility and avoid wasting time on a mismatched relationship.

Romantic Questions for Your Man

What’s a song that always reminds you of us, and why? What’s a song that always reminds you of us, and why?
What’s a little thing I do that always makes you smile? What’s a little thing I do that always makes you smile?
What’s the most meaningful gift you’ve ever received from me? What’s the most meaningful gift you’ve ever received from me?
How has our relationship changed you for the better? How has our relationship changed you for the better?
What’s your idea of a perfect date? What’s your idea of a perfect date?
How would you like to celebrate our love when we’re old and gray? How would you like to celebrate our love when we’re old and gray?
How do you define true love, and what are its key components for you? How do you define true love, and what are its key components for you?
How do you feel when we’re apart? How do you feel when we’re apart?
How do you most enjoy receiving love from me? How do you most enjoy receiving love from me?
If you could write a love story about us, what title would you choose? If you could write a love story about us, what title would you choose?
What was your impression of me after our first date? What was your impression of me after our first date?
How would you describe our first kiss? How would you describe our first kiss?
When did you realize you were in love with me? When did you realize you were in love with me?
How do you feel when I say “I love you”? How do you feel when I say “I love you”?
What’s your favorite thing about my personality? What’s your favorite thing about my personality?
What’s the sweetest thing I’ve ever done for you? What’s the sweetest thing I’ve ever done for you?
What’s the most memorable date we’ve had? What’s the most memorable date we’ve had?
What’s the most romantic place we’ve been together? What’s the most romantic place we’ve been together?
What’s one thing you’ve always wanted to do together? What’s one thing you’ve always wanted to do together?
How do you see our love evolving over the years? How do you see our love evolving over the years?
How do you feel when you see me after a long day? How do you feel when you see me after a long day?
How do you feel when we hold hands? How do you feel when we hold hands?
How do you feel when we cuddle? How do you feel when we cuddle?
How do you feel when we dance together? How do you feel when we dance together?
What makes you feel loved in a relationship? What makes you feel loved in a relationship?
How do you express your love for me without words? How do you express your love for me without words?
What’s your favorite way to spend time with me? What’s your favorite way to spend time with me?
What’s your favorite way to say “I love you”? What’s your favorite way to say “I love you”?
What’s the most romantic thing you’d like to do for me? What’s the most romantic thing you’d like to do for me?
How do you feel about celebrating anniversaries? How do you feel about celebrating anniversaries?
What’s your idea of a perfect romantic evening? What’s your idea of a perfect romantic evening?
What’s the most thoughtful gift you’ve ever given me? What’s the most thoughtful gift you’ve ever given me?
What song reminds you of me? What song reminds you of me?
How do you feel when I surprise you with something special? How do you feel when I surprise you with something special?
What’s the most romantic compliment I’ve ever given you? What’s the most romantic compliment I’ve ever given you?

According to Dr. Gary Chapman, author of The 5 Love Languages, regularly expressing love and affection through words and actions is essential for maintaining a healthy relationship. Romantic questions help to keep the spark alive and the love strong.^[¹^]

However, a study published in PLOS ONE highlights that individuals with unresolved issues from past relationships or unrealistic expectations influenced by media portrayals of romance may feel uneasy with romantic gestures.^[²^]

So, keep this in mind when trying to ignite some romance; sometimes, it may feel awkward and uncomfortable not because he doesn’t like or love you, but due to his past experiences and learned behaviors about romance.

As always, the best way to know is by asking thoughtful questions, listening attentively (reflective listening is my personal favorite), and communicating openly.

Being in a romantic couple begs for romantic questions.

Questions like these help you unlock a deeper emotional connection and express your love for each other. They are some of the best ways to flirt and reignite the romance in your relationship, creating sweet memories.

These flirty questions are perfect for date nights, adding an extra layer of intimacy and fun to your time together.

Juicy Questions to Ask Your Boyfriend

What’s the most bizarre rumor you’ve heard about yourself? What’s the most bizarre rumor you’ve heard about yourself?
What’s the weirdest thing you’ve done out of jealousy? What’s the weirdest thing you’ve done out of jealousy?
Have you ever been caught in a lie? What happened? Have you ever been caught in a lie? What happened?
What’s the most romantic gesture you’ve ever made? What’s the most romantic gesture you’ve ever made?
Have you ever snooped through someone’s stuff? Did you find anything interesting? Have you ever snooped through someone’s stuff? Did you find anything interesting?
Have you ever had a forbidden or secret relationship? Have you ever had a forbidden or secret relationship?
Have you ever secretly liked a friend’s partner? What happened? Have you ever secretly liked a friend’s partner? What happened?
What’s your most embarrassing moment at school or work? What’s your most embarrassing moment at school or work?
What’s the most regrettable post or comment you’ve ever made on social media? What’s the most regrettable post or comment you’ve ever made on social media?
Have you ever created a Finsta account to spy on someone? Why? Have you ever created a Finsta account to spy on someone? Why?

Juicy questions are all about uncovering those little secrets and stories that add spice to your conversations.

They can lead to laughter, shared confessions, and maybe even some inside jokes.

While you don’t need to know every detail about your partner, sometimes these questions reveal surprising facts. You might think you know everything about him only to discover he spent 24 hours in jail for trying to break into his crush’s house to retrieve an ill-timed love letter.

We are all boxes of chocolate, I’m telling you.

Fun Questions to Ask Him

If you could swap lives with a character from any book for a day, who would it be and why? If you could swap lives with a character from any book for a day, who would it be and why?
If you could only eat one type of cuisine for the rest of your life, which would it be? If you could only eat one type of cuisine for the rest of your life, which would it be?
If you could instantly learn any language fluently, which one would you choose? If you could instantly learn any language fluently, which one would you choose?
What’s the most unusual talent you have that few people know about? What’s the most unusual talent you have that few people know about?
What’s the most ridiculous fact you know that always makes you laugh? What’s the most ridiculous fact you know that always makes you laugh?
If you could live in any fictional universe, which one would you choose? If you could live in any fictional universe, which one would you choose?
What’s your go-to karaoke song and why? What’s your go-to karaoke song and why?
What’s your favorite childhood memory? What’s your favorite childhood memory?
If you could have any job in the world, regardless of salary, what would it be? If you could have any job in the world, regardless of salary, what would it be?
Who’s one person you’d want to be stranded on a deserted island with and why? Who’s one person you’d want to be stranded on a deserted island with and why?

Fun questions are great for lightening the mood and making each other laugh while still uncovering the inner workings of their brain.

They’re perfect for killing time on a road trip or just enjoying a lazy Sunday together.

For instance, if the one type of cuisine he could eat for the rest of his life is not Italian, pasta la vista, baby.

Questions to Test Your Boyfriend’s Love

Does he love you or is he just here for the snacks? Asking questions is the only way to know.

With these 25 deep questions, you’ll uncover whether he sees you as just a side of fries — fun and enjoyable but not the main feast — or if he understands that you’re the whole meal.

What was your first impression of me, and how has it evolved? What was your first impression of me, and how has it evolved?
What qualities do you admire most about me? What qualities do you admire most about me?
What’s the biggest lesson you've learned from me? What’s the biggest lesson you've learned from me?
What’s your most cherished memory of us together, and why? What’s your most cherished memory of us together, and why?
What’s the most romantic thing I've ever done for you? What’s the most romantic thing I've ever done for you?
Is there a song that makes you think of us, and why? Is there a song that makes you think of us, and why?
When we're apart, what emotions do you experience? When we're apart, what emotions do you experience?
How does our love feel to you? How does our love feel to you?
How do you feel when I achieve something great? How do you feel when I achieve something great?
What goes through your mind after we fight or disagree? What goes through your mind after we fight or disagree?
How do you show your love for me daily? How do you show your love for me daily?
How do you like me to show you my love daily? How do you like me to show you my love daily?
Where do you see our life together in the next ten years? Where do you see our life together in the next ten years?
How do you envision supporting me through my dreams and goals? How do you envision supporting me through my dreams and goals?
How do you envision me supporting you through your dreams and goals? How do you envision me supporting you through your dreams and goals?
How do you see us growing together as individuals and as a couple? How do you see us growing together as individuals and as a couple?
What are your thoughts on starting a family? What are your thoughts on starting a family?
What’s the most crucial area we need to work on? What’s the most crucial area we need to work on?
What’s the biggest challenge we've overcome, and how did it shape us? What’s the biggest challenge we've overcome, and how did it shape us?
Do you ever experience feelings of jealousy or insecurity in our relationship? Do you ever experience feelings of jealousy or insecurity in our relationship?
What sacrifices have you made for our relationship, and how do they make you feel? What sacrifices have you made for our relationship, and how do they make you feel?
What does commitment mean to you in our relationship? What does commitment mean to you in our relationship?
Can you describe a moment when you felt truly connected to me? Can you describe a moment when you felt truly connected to me?
What are your thoughts on forgiveness and how it applies to us? What are your thoughts on forgiveness and how it applies to us?
How do you prioritize our relationship amidst other responsibilities? How do you prioritize our relationship amidst other responsibilities?

These are hard questions to ask but they will let you get a better understanding of the depth of your emotional intimacy and verify whether you are both on the same page.

A study in the Personality and Social Psychology Bulletin shows that by discussing memories, feelings, future goals, and daily love gestures, couples can strengthen their bond, making each partner feel valued and understood, ultimately enriching their relationship.^[³^]

After all, if you don’t share the same long-term relationship vision, it makes sense not to waste any more time, right?Serious Questions to Ask Your Boyfriend

If you could change one decision you’ve made in the past, what would it be and why? If you could change one decision you’ve made in the past, what would it be and why?
What’s a personal value or principle you would never compromise on, no matter what? What’s a personal value or principle you would never compromise on, no matter what?
What’s a personal accomplishment you’re most proud of, and why does it hold such significance for you? What’s a personal accomplishment you’re most proud of, and why does it hold such significance for you?
How do you envision balancing personal ambitions with a committed relationship? How do you envision balancing personal ambitions with a committed relationship?
How do you approach making difficult decisions, especially when they affect others? How do you approach making difficult decisions, especially when they affect others?
What’s a major life experience that significantly altered your worldview? What’s a major life experience that significantly altered your worldview?
If you had to choose a single legacy to leave behind, what would it be and why? If you had to choose a single legacy to leave behind, what would it be and why?
What does emotional intimacy mean to you, and how do you nurture it? What does emotional intimacy mean to you, and how do you nurture it?
What’s a belief or philosophy you live by, and how does it influence your daily actions? What’s a belief or philosophy you live by, and how does it influence your daily actions?
How do you define happiness, and what steps do you take to achieve it in your life? How do you define happiness, and what steps do you take to achieve it in your life?

Serious questions don’t have to be boring. In fact, they can be some of the most interesting questions to ask, whether you’ve just met or have been together for years.

They can help you understand your boyfriend’s long-term goals and values.

While they might not be the typical conversation starters, these thought-provoking questions can lead to deep, meaningful discussions that reveal his true aspirations and beliefs.

Random Questions to Ask Your Guy

What’s the most random item you have in your room right now, and how did it get there? What’s the most random item you have in your room right now, and how did it get there?
What’s the weirdest thing you’ve ever eaten and actually liked? What’s the weirdest thing you’ve ever eaten and actually liked?
What’s the strangest habit you’ve picked up during your life? What’s the strangest habit you’ve picked up during your life?
What’s the most bizarre superstition you’ve ever heard of or believed in? What’s the most bizarre superstition you’ve ever heard of or believed in?
If you could turn any activity into an Olympic sport, what would you have a good chance of winning a medal in? If you could turn any activity into an Olympic sport, what would you have a good chance of winning a medal in?
What’s the most embarrassing song you secretly love to listen to? What’s the most embarrassing song you secretly love to listen to?
If you could instantly become an expert in any field or activity, what would it be and why? If you could instantly become an expert in any field or activity, what would it be and why?
What’s the most out-of-character thing you’ve ever done? What’s the most out-of-character thing you’ve ever done?
What’s the most random thing you’ve Googled recently? What’s the most random thing you’ve Googled recently?
What nickname would you give yourself and why? What nickname would you give yourself and why?

Instead of asking about his favorite movie or TV show, hit him with these random questions. Some people might not agree, but I would totally ask these on a first date. But hey, that’s just me.

These questions can lead to unexpected stories and shared laughter, whether you’re in a short-term fling or a long-term relationship. They’re great for breaking the monotony and discovering new things about each other.

Random questions are perfect for surprising your boyfriend and keeping conversations interesting. Keep him on the edge — is she incredibly curious or a bit insane?

Questions to Ask Him Over Text

Thanks to the invention of instant communication, being apart doesn’t have to leave you hanging — these 25 playful and thought-provoking questions will help you gauge his feelings over text.

What are your core values when it comes to love and relationships, and how do you apply them in our relationship? What are your core values when it comes to love and relationships, and how do you apply them in our relationship?
What’s the best piece of relationship advice you’ve ever received, and how do you apply it in our relationship? What’s the best piece of relationship advice you’ve ever received, and how do you apply it in our relationship?
How do you feel when we spend quality time together? How do you feel when we spend quality time together?
What’s one thing you appreciate most about our relationship? What’s one thing you appreciate most about our relationship?
How do you feel when I flirt with you? How do you feel when I flirt with you?
What’s the most attractive thing about our relationship? What’s the most attractive thing about our relationship?
What’s one quality you think makes our relationship unique? What’s one quality you think makes our relationship unique?
How do you think we complement each other as a couple? How do you think we complement each other as a couple?
How do you feel about exploring new things together as a couple? How do you feel about exploring new things together as a couple?
What’s one thing you love about our communication style? What’s one thing you love about our communication style?
What’s one thing you don’t love about our communication style? What’s one thing you don’t love about our communication style?
How do you think we’ve both grown since we started dating? How do you think we’ve both grown since we started dating?
What’s one thing you’re willing to work on to improve our relationship? What’s one thing you’re willing to work on to improve our relationship?
What’s one thing you think we should try together to strengthen our bond? What’s one thing you think we should try together to strengthen our bond?
What’s your favorite memory of us so far? What’s your favorite memory of us so far?
What’s the most intimate moment you remember sharing with me? What’s the most intimate moment you remember sharing with me?
What are your thoughts and feelings about our future together? What are your thoughts and feelings about our future together?
What’s the funniest thing that’s ever happened on one of our date nights that you never told me about out of embarrassment? What’s the funniest thing that’s ever happened on one of our date nights that you never told me about out of embarrassment?
If we were characters in a comedy show, which show would it be and why? If we were characters in a comedy show, which show would it be and why?
What’s one ridiculous thing you’d love to do with me just for fun? What’s one ridiculous thing you’d love to do with me just for fun?
How do you feel about PDA (public displays of affection)? How do you feel about PDA (public displays of affection)?
How do you feel about discussing your past relationships with me? How do you feel about discussing your past relationships with me?
How do you balance your personal goals with our relationship goals? How do you balance your personal goals with our relationship goals?
What’s a past experience that significantly influenced your views on love and relationships, and how does it affect our relationship? What’s a past experience that significantly influenced your views on love and relationships, and how does it affect our relationship?
What are your main priorities in life right now, and how do you see our relationship fitting into those priorities? What are your main priorities in life right now, and how do you see our relationship fitting into those priorities?

Texting can be a powerful way to stay connected and express love.

It often encourages people to be bolder and more honest because it provides time to reflect, leading to more thoughtful and precise responses.

By asking your boyfriend these questions over text, you can get the real answers — no need to resort to the old “loves me, loves me not” flower petal plucking!

Important Questions to Ask Your Boyfriend

What are your deal-breakers in a relationship? What are your deal-breakers in a relationship?
How do you handle conflict in a relationship? How do you handle conflict in a relationship?
How do you prioritize self-care and mental health? How do you prioritize self-care and mental health?
What are your financial goals? What are your financial goals?
What is your definition of failure? What is your definition of failure?
What is your stance on political and social issues? What is your stance on political and social issues?
How many dogs is too many dogs? How many dogs is too many dogs?
How important is family to you? How important is family to you?
Do you want to get married? Do you want to get married?
Do you want to have kids? Do you want to have kids?

I kept those questions simple because there’s no point in overcomplicating it.

I believe any person should have an answer to these questions off the top of their head.

Of course, things change over time, but these relationship questions focus more on personal goals and values, not just values in a relationship. It’s a good idea to date people who have given these subjects some thought.

Trick Questions to Ask Your Boyfriend

He’s halfway through a mountain of ironing, completely zoned out, when you casually ask, “If you had to pick between me and your favorite hobby, which would you choose?”

Catching him off guard can yield the most honest and spontaneous, often hilarious responses. These 25 trick questions are perfect for revealing his true feelings!

If I turned into a cartoon character for a day, who would you hope I become? If I turned into a cartoon character for a day, who would you hope I become?
Would you still like me if I had a third eye in the middle of my forehead? Would you still like me if I had a third eye in the middle of my forehead?
If I suddenly developed the ability to talk to animals, which animal would you be most worried about me befriending? If I suddenly developed the ability to talk to animals, which animal would you be most worried about me befriending?
If you could swap lives with me for a day, what’s the first thing you’d do? If you could swap lives with me for a day, what’s the first thing you’d do?
Would you still love me if I had to wear a clown costume everywhere we went for a month? Would you still love me if I had to wear a clown costume everywhere we went for a month?
Would you rather have me always whisper or always shout? Would you rather have me always whisper or always shout?
Would you still like me if I decided to become a professional mime? Would you still like me if I decided to become a professional mime?
Would you still like me if my laugh sounded like a foghorn? Would you still like me if my laugh sounded like a foghorn?
Would you still love me if I spontaneously started speaking in Shakespearean English all the time? Would you still love me if I spontaneously started speaking in Shakespearean English all the time?
If I insisted on wearing socks with sandals, would you still be seen in public with me? If I insisted on wearing socks with sandals, would you still be seen in public with me?
Would you help me bury a body if I accidentally ran over a garden gnome? Would you help me bury a body if I accidentally ran over a garden gnome?
If we had to relive one day over and over, which day would you choose? If we had to relive one day over and over, which day would you choose?
Would you let me name our first pet after a character from my favorite TV show? Would you let me name our first pet after a character from my favorite TV show?
Would you still like me if I started dressing like a character from the 1980s? Would you still like me if I started dressing like a character from the 1980s?
If I challenged you to a dance-off in the middle of the grocery store, would you participate? If I challenged you to a dance-off in the middle of the grocery store, would you participate?
Would you rather I have a permanent duck face or constantly do the robot when I walk? Would you rather I have a permanent duck face or constantly do the robot when I walk?
If I decided to take up yodeling as a hobby, would you support me? If I decided to take up yodeling as a hobby, would you support me?
If I painted our bedroom neon green without consulting you, how would you react? If I painted our bedroom neon green without consulting you, how would you react?
Would you switch places with me for a day if it meant you had to wear high heels the whole time? Would you switch places with me for a day if it meant you had to wear high heels the whole time?
If I insisted on doing all the grocery shopping while wearing a superhero costume, would you join me? If I insisted on doing all the grocery shopping while wearing a superhero costume, would you join me?
Would you rather I always smelled like your least favorite food or sounded like your least favorite celebrity? Would you rather I always smelled like your least favorite food or sounded like your least favorite celebrity?
Would you still like me if I could only tell dad jokes for an entire month? Would you still like me if I could only tell dad jokes for an entire month?
Would you rather I had an uncontrollable urge to photobomb strangers or make awkward small talk with everyone we meet? Would you rather I had an uncontrollable urge to photobomb strangers or make awkward small talk with everyone we meet?
If I decided to take a vow of silence for a week, how would you communicate with me? If I decided to take a vow of silence for a week, how would you communicate with me?
If I replaced all our furniture with bean bag chairs, how long would you last before replacing them? If I replaced all our furniture with bean bag chairs, how long would you last before replacing them?
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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?
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?
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?

If you could date any celebrity, who would it be? If you could date any celebrity, who would it be?
Would you still love me if I turned into a worm? Would you still love me if I turned into a worm?
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?

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?
If I asked you to stop seeing your best friend, would you? If I asked you to stop seeing your best friend, would you?
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?
Do you think I'm more like a cat or a dog? Do you think I'm more like a cat or a dog?
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?
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?

Would you rather be rich and single or poor but with me? Would you rather be rich and single or poor but with me?
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?
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?
What’s one secret you’ve never told me? What’s one secret you’ve never told me?
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?
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?
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?

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?
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?
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?
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?
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?
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?
If I were a color, which one would I be and why? If I were a color, which one would I be and why?
Would you rather forget me or forget everything else in your life? Would you rather forget me or forget everything else in your life?
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?
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, channel your inner Phoebe Buffay and unleash these delightfully random, tricky, and fun questions on him!

His answers will be a mix of honesty and hilarity.

Just like Phoebe’s peculiar yet undeniable charm, these questions will reveal just how deep his love — and patience — truly runs. Could he be your lobster?

Trick Questions 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.

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.)
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?
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?
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?
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?
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?
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?
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? ]
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?
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?
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?

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?)
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?
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?
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?
Would you rather live without your phone or without me? Would you rather live without your phone or without me?
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?
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?
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?
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?)

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.)
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?
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?
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?
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?
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?
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?
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?
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?
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

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.

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?
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?
If you were a cartoon character, who would you be? If you were a cartoon character, who would you be?
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?
Would you rather have a pet dinosaur or a pet dragon? Would you rather have a pet dinosaur or a pet dragon?
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?
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?

Would you rather have spaghetti for hair or maple syrup for sweat? Would you rather have spaghetti for hair or maple syrup for sweat?
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?
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?
Would you rather always have to whisper or always have to shout? Would you rather always have to whisper or always have to shout?
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?
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?
If you could be invisible for a day, what would you do? If you could be invisible for a day, what would you do?
Would you rather have a third arm or a third leg? Would you rather have a third arm or a third leg?
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?
Would you rather be a giant hamster or a tiny rhino? Would you rather be a giant hamster or a tiny rhino?
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?
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?
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?

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?
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?
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?
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?
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?
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?
Would you rather be a wizard or a superhero? Would you rather be a wizard or a superhero?
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?
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?
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 for Him

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.

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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?

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?
If we could write our own love story, how would it begin? If we could write our own love story, how would it begin?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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?
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

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.

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?
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?
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?
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?
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?
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?
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?
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?
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?
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?

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?
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?
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?
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?
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?
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?
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?
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?
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?
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?

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?
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?
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?
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?
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?
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?
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?
If we could only achieve one goal together, what would it be? If we could only achieve one goal together, what would it be?
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!

Cute Questions to Ask Your Guy

What is the first thing you noticed about me?

If you had to describe us in three words, what would they be? If you had to describe us in three words, what would they be?
What is a little thing I do that always makes you laugh? What is a little thing I do that always makes you laugh?
How do you like to be comforted when you’re sad? How do you like to be comforted when you’re sad?
What is a dream destination you’d love to visit with me? What is a dream destination you’d love to visit with me?
What do you think is the key to a happy relationship? What do you think is the key to a happy relationship?
What are your love languages? What are your love languages?
How do you like to celebrate special occasions? How do you like to celebrate special occasions?
What is something you appreciate about our relationship? What is something you appreciate about our relationship?
What is a new hobby or activity you would like us to try together? What is a new hobby or activity you would like us to try together?

Cute questions focus on the lighter, more playful side of your relationship, often bringing smiles and laughter.

These questions to ask your boyfriend are perfect for keeping things fun and lighthearted, especially when dating someone new.

Whether you’ve been together for one year or nine days, these cute questions are great for any stage of your relationship.

Weird Questions to Ask Him

If you could merge two animals to create the ultimate pet, which ones would you combine, and why? If you could merge two animals to create the ultimate pet, which ones would you combine, and why?
If you were a ghost, how would you haunt people? If you were a ghost, how would you haunt people?
What’s the weirdest conspiracy theory you believe? What’s the weirdest conspiracy theory you believe?
If your life had a theme song that played every time you entered a room, what would it be? If your life had a theme song that played every time you entered a room, what would it be?
If you could have an extra body part, what would it be and where would you put it? If you could have an extra body part, what would it be and where would you put it?
If you were a kitchen appliance, which one would you be and why? If you were a kitchen appliance, which one would you be and why?
If you could give your pet a human job, what job would it have? If you could give your pet a human job, what job would it have?
If you could change your hair to any color of the rainbow everyday, would you do it and what would be your favorite color? If you could change your hair to any color of the rainbow everyday, would you do it and what would be your favorite color?
What would you do if you woke up one day and found out you were invisible? What would you do if you woke up one day and found out you were invisible?
What will be written on your gravestone? What will be written on your gravestone?

Weird questions are great for adding a bit of fun and unpredictability to your conversations.

These questions can lead to hilarious stories and shared laughter, making him laugh and open up about his unique brand of weird.

They’re perfect for keeping things exciting and discovering your boyfriend’s quirky side. Whether you’re still getting to know each other or have been together for a while, these questions provide a unique way to share stories and bond, ensuring your relationship stays fresh and fun.

Men need this one thing

In my experience, the missing link in a relationship is failing to understand what your guy is thinking at a deep level.

Because men see the world differently to you and they want different things from a relationship.

Not knowing what men need can make a passionate and long lasting relationship — something that men crave just as much as women — really difficult to achieve.

While getting your guy to open up and tell you what he’s thinking can feel like an impossible task… there’s a new way to understand what’s driving him.

James Bauer is one of the world’s leading relationship experts.

And in his new video, he reveals a new concept which brilliantly explains what really drives men. He calls it the hero instinct.

Simply put, men want to be your hero. Not necessarily an action hero like Thor, but he does want to step up to the plate for the woman in his life and be appreciated for his efforts.

The hero instinct is probably the best kept secret in relationship psychology. And I think it holds the key to a man’s love and devotion for life. You can watch the video here.

Here’s a link to James Bauer’s free video again. He provides a terrific overview of the hero instinct, and gives several free tips to trigger it in your man.

Conclusion

Want to get closer to your boyfriend? Just ask good questions!

Heat things up with spicy ones, dig into his values with deep ones, and uncover fun secrets with juicy ones. Keep things light with fun questions, check compatibility with serious ones, and toss in random questions for surprises.

Honest chats and shared experiences make your bond stronger. So go ahead, ask your boyfriend these questions and enjoy getting to know him even better!

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

FAQs

How can I test my boyfriend’s true love?

You can test your boyfriend’s true love by observing his actions and consistency over time, communicating openly about your needs and expectations, and seeing how he responds to challenging situations. Genuine love is shown through respect, support, and effort in the relationship.

What is the hardest question to ask your boyfriend?

The hardest question to ask your boyfriend is often about the future of your relationship. Asking “Where do you see our relationship going?” can be difficult but necessary for understanding his long-term intentions and commitment.

How can I communicate better?

To communicate better, practice active listening, express your thoughts clearly and respectfully, and use “I” statements to share your feelings without blaming. Regularly check in with each other to ensure mutual understanding and address any issues promptly.

What are trick questions, and why should you ask them?

Trick questions are designed to catch your partner off guard and get a surprising or humorous response. They help you know your partner better, start the conversation, and spend quality time together. Asking trick questions can lead to interesting and memorable moments, helping to strengthen your bond and keep the relationship exciting.

What is the hardest question to ask my boyfriend?

One of the hardest questions to ask your boyfriend is about the future of your relationship. For example, “Where do you see us in five years?” This thought-provoking question helps you understand his feelings and future plans, providing valuable insights into his commitment and vision for your relationship.

What are some ways to spice up a relationship?

Some ways to spice up a relationship are trying something new together, like a hobby or a class, planning surprise dates, or just changing up your routine. Even small gestures, like leaving notes or planning a weekend getaway, can make a difference. It’s about keeping things fresh and interesting.

References

Fraley, R. C., & Shaver, P. R. (2016). Regulation of romantic love feelings: Preconceptions, strategies, and feasibility. PLOS ONE, 11(8), e0161087.
https://doi.org/10.1371/journal.pone.0161087 ↩︎
Chapman, G. (1992). The 5 love languages: The secret to love that lasts. Northfield Publishing. ↩︎
Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: A procedure and some preliminary findings. Personality and Social Psychology Bulletin, 23(4), 363–377.
https://doi.org/10.1177/0146167297234003 ↩︎

Author

Milena J. Wisniewska

Milena might not be a relationship professor, but she's definitely been through it all, learned her lessons, and is here to spill the tea. She combines the wisdom of renowned relationship specialists with her own romantic adventures to offer relatable and practical advice.
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350 Questions to Ask Your Boyfriend to Get to Know Him Better