100+ Romantic Questions To Ask Your Boyfriend To Make Him Laugh

You clearly adore your boyfriend and love hearing him laugh, and thankfully, there are many ways to encourage that! Whether you’ve been together for five days or five years, there’s always something new to learn about each other. Beyond the usual questions, digging into more thoughtful, daring, and even “spicy” questions can reveal new facts of his personality, deepen your connection, and even unveil sides of yourself you hadn’t seen before.

By asking questions that might push your comfort zone, you’re inviting him to open up in thrilling new ways, all while building crucial trust. These questions are perfect for sparking meaningful conversations, keeping things fresh, and understanding his desires more intimately. Have a look at the list below to check what romantic questions you can ask your boyfriend to make him laugh.

Deep Questions To Ask Your Boyfriend

What’s something you wish more people understood about you, but you find hard to express?
What’s a piece of wisdom someone gave you that really stuck with you and changed your perspective?
Can you share a favorite memory from your childhood that always brings a smile to your face?
If you could change one thing about yourself, big or small, what would it be and why?
Who’s someone you truly admire, and what qualities do they possess that you aspire to?
What makes you feel a sense of accomplishment or deep pride?
Do you tend to trust your gut feeling when making decisions?
Do you believe in the concept of kindred spirits or destiny when it comes to love?
What’s your stance on whether actions have consequences that come back around (karma)?
What does being a “good person” mean to you?
How do you feel about social media and its role in our lives?
How do you prefer to communicate when something important is on your mind?
When was the last time you felt emotional enough to cry, and what brought it on?
What’s a specific habit you’d really like to let go of?
What’s one of your biggest fears or anxieties?
Can you tell me about a time you felt really embarrassed? What happened?
If you could go back and whisper something to your younger self, knowing what you know now, what would it be?
What truly inspires you and keeps you moving forward?
How would you describe your perfect life, if there were no limitations?
What are the top three things that are most important to you right now?
What does true success look like to you?
If you knew you only had 24 hours left, how would you spend them?
What’s something you’ve always wanted to learn or try?

Good Question To Ask Him So You Can Know Him Better

What’s a vivid memory you have from the neighborhood where you grew up?
If you could revisit one place from your childhood, where would it be and why?
What was your absolute favorite way to spend a free afternoon when you were a kid?
Tell me about the most memorable moment with your first pet, even if it was silly.
What was the first album or song that made a real impact on you?
If you could instantly learn to play any instrument, which one would it be?
Tell me your dream romantic escape—where would we go and what would we do?
If you had a magic wand and could instantly master three new languages, which would you choose?
What’s that one meal you could happily eat every single day for the rest of your life without getting tired of it?
When you pack for a trip, are you a minimalist with just a carry-on, or do you bring everything but the kitchen sink?
What’s a funny or sweet memory you have from your first kiss?
If you could map out your next five international adventures, where would they be?

Funny Questions To Ask Your Boyfriend

What’s the most random thing you’ve ever Googled out of pure curiosity?
What’s the most embarrassing way you’ve ever injured yourself?
What’s the funniest or strangest belief you had as a kid that you later realized was totally false?
Describe the most bizarre dream you can remember having.
If you could only eat one type of food for the rest of your life, what glorious (or terrible) meal would it be?
Which fictional character do you secretly wish you could hang out with in real life?
What’s the funniest or most absurd thing you’ve scrolled past on social media recently?
Do you have any hidden, quirky talents that no one knows about?
What’s the most questionable fashion trend you ever fully embraced?
What’s the funniest text message you’ve ever received that made you laugh out loud?
Which Disney character do you think you’re most like, and why?
If you could have any animal in the world as a pet, even a mythical one, what would it be?
If you suddenly found yourself able to haunt someone as a friendly ghost, who would be your target and what silly things would you do?
If you could have one superpower, what would it be and how would you use it in the most ordinary way possible?
Are you more of a sneakers person or a sandals person?
Who would be your dream actor to play you in a movie about your life, and why?
Which historical figure would you love to invite to a casual dinner party?
If you could go to any concert, past or present, with any celebrity, who would it be and who would you go see?
What’s the silliest video on the internet that never fails to make you crack up?
If you could only keep one app on your phone, which one would survive the purge?
What’s your all-time favorite meme that perfectly captures your sense of humor?
When it comes to condiments, are you a mustard loyalist or a ketchup connoisseur?
If you were a sandwich, what kind of sandwich would you be, and what would your ingredients represent?
What’s a word you absolutely can’t stand to hear?
If you were a contestant on a reality TV show, which one do you think you’d actually win?
If you could travel back in time to live in any other decade, which one would you pick and why?
What’s the most ridiculous thing you’ve ever bought just because it made you laugh?
What’s the absolute worst joke you’ve ever heard that you still remember?
If you suddenly won a massive lottery, what’s the first utterly silly thing you’d do with the money?
Would you rather have a giant dog that’s as big as a horse, or a giant cat that’s the size of a lion?
If you had to plan your absolute last meal, what would be on the menu?
If you somehow ended up in prison, what do you think would be the most likely (and perhaps shocking) reason?

Want to keep the fun going? Try these This or That Questions for some lighthearted laughs.

Dirty Questions to Ask Your Boyfriend

What’s an adventure you’ve secretly wanted us to try together, just the two of us?
What usually makes you want to make the first move in our intimate moments?
What’s something I do, maybe without even realizing it, that you find incredibly alluring?
When it comes to connecting throughout the day, do you prefer a little playful banter via text or a deeper, more intimate chat later in the evening?
If we could disappear for a spontaneous, passionate night, where would be your dream destination?
Have you ever experimented with blindfolds or restraints?
When you’re missing me, what’s a particular thought that often crosses your mind?
If I were to plan a surprise for you, what kind of romantic or thrilling elements would you hope it includes?
What’s a fantasy you’ve had about a complete stranger that you wouldn’t mind sharing?
What’s one specific thing about me that consistently makes your pulse quicken?
What’s the most provocative thing someone has ever said to you?
Do you have a favorite outfit of mine that you particularly enjoy seeing me in?
What’s the most flattering compliment you’ve ever received about your body?
Can you recall an awkward or funny moment that happened during a make-out session or intimate encounter?
Have you ever had a dream about a close friend that made you blush when you woke up?
What’s the most daring text message you’ve sent or received?
Where’s your absolute favorite spot on your body to be kissed?
What’s one thing you’d love me to do more often to spice things up between us?
What happened in the weirdest sex dream you have ever had?

If you love playful moments, don’t miss these fun and thoughtful Would You Rather Questions for couples.

Relationship Questions to Ask Your Boyfriend

Can you describe the magic (or maybe the awkwardness!) of your very first kiss?
What does an ideal “couple dynamic” look like to you? What aspects of a relationship do you truly value?
Have you ever had a close friendship that blurred the lines into something more?
What’s the most memorable “bad date” story you have, and what made it so cringeworthy?
What’s the most outrageous (or funniest) thing you’ve ever done to catch someone’s attention?
When you think about us, what’s a favorite memory that always brings a smile to your face?
If you were to design the perfect date for us, what would it involve from start to finish?
Do you find yourself drawn to a particular “type” of person, and if so, what are those qualities?
What’s the most romantic gesture you’ve ever made for someone, or perhaps received?
What’s your vision for a truly unforgettable marriage proposal (whether for yourself or someone else)?
Where do you envision yourself and your life ten years from now? What does that picture look like?
Do you see children in your future, and if so, what kind of parent do you imagine yourself being?

Personal Questions To Ask Your Boyfriend

What’s a movie, book, or show that you could watch/read over and over again?
If you had to pick one superhero to be your best friend, who would it be?
What’s a song or artist that always puts you in a good mood?
What’s your absolute favorite meal – the one you could eat anytime, anywhere?
Which season do you love the most, and why?
What’s one of your most cherished memories from childhood?
Are you more of a morning person or a night owl?
Do you have any unusual hobbies or interests that most people don’t know about?
How did you and your best friend originally meet?
What’s one small thing you couldn’t imagine living without?
What’s one of your biggest “guilty pleasures”?
What do you think is the most interesting thing about yourself?
If you could instantly travel to one new place you’ve never been, where would it be?
What does a “perfect day” look like for you, from start to finish?
How would you describe your relationship with your parents or guardians?
What’s one of your biggest dreams for the future?
How do you prefer to receive love and affection – what makes you feel most appreciated? (This relates to “love language” without using the term directly.)
Are you generally more energized by being around people or by having quiet time alone?
Would you rather spend a cozy night in or go out and explore?

Juicy Questions To Ask Your Boyfriend

If you could instantly gain mastery in one incredibly niche skill (like competitive cheese rolling or underwater basket weaving), what would it be and why?
What’s a minor everyday mystery that you often ponder, even if it’s something silly like “why do socks always disappear in the laundry?”
If your life had a “loading screen” before you started each day, what witty or profound tip would it display?
What’s a scent that immediately transports you back to a very specific, vivid memory?
If you had to swap lives with any inanimate object for a day, what would you choose and what do you think its day would be like?
What’s one technological advancement from a sci-fi movie that you desperately wish was real right now?
If animals could talk, which species do you think would be the most annoying, and why?
What’s a food combination that you absolutely love but others find really strange or disgusting?
If you were a character in a video game, what would your unique, slightly odd special ability be?
What’s a common phrase or idiom that makes absolutely no sense when you think about it literally?
If you could have a conversation with your pet (if you have one), what’s the first question you’d ask them?
What’s the most unusual or unexpected compliment you’ve ever received?
If you had to narrate your own life, what kind of voice would the narrator have (e.g., deep and dramatic, light and sarcastic)?
What’s one thing you’re surprisingly particular about that others might not notice?
If you could design a new national holiday, what would it be called and how would people celebrate it?

Cute Questions To Ask Your Boyfriend

What’s a passion you have that you rarely get to talk about, but you’d love to share more?If we had a spontaneous candlelit dinner right now, what would be the dreamiest setting for it, real or imaginary?
Imagine we’re walking hand-in-hand on a beautiful beach at sunset. What’s the first thing that comes to your mind that you’d want to tell me?
If we could jump in the car right now for a long drive to anywhere, just the two of us, where would we go and what song would be playing?
What’s a tiny, everyday moment that makes you feel a big surge of love for me?
Thinking back, what was your absolute favorite thing about your first crush (besides their looks!)?
What’s one small, silly thing that I do that always makes you smile, even when you try not to?
If we could create our own little world, what’s one quirky tradition we’d definitely have?
What’s a memory of us that, whenever you think of it, just makes your heart feel warm?
If you could write a “thank you” note to something small I’ve done for you, what would it be?
What’s something you’re secretly looking forward to doing with me in the future?
What’s a compliment someone gave you recently that made you feel really good, and why?
What’s your favorite way to just relax and be completely comfortable when you’re with me?
If our relationship had a signature cuddle position, what would it be?
What’s one thing about me that you just find incredibly endearing?
When it comes to meals, do you secretly love it when I cook for you, or do you prefer taking the lead in the kitchen for us?
Do you prefer our date nights to be spontaneous adventures or carefully planned evenings?

Romantic Questions To Ask Your Boyfriend

What first thing came to mind the very first time you saw me?
What’s your absolute favorite romantic memory that we’ve made together so far?
How do you personally define “falling in love”?
Was there a specific moment when you knew, or started to realize, that you were in love with me?
How do you naturally prefer to express your love and affection to someone?
What’s your idea of the perfect romantic date? Is it a cozy seaside candlelight dinner, a lively jazz bar night, or something else entirely?
What’s your dream proposal scenario? I’d love to hear all the details.
What’s the most intimate or thoughtful thing you’ve ever done for someone you cared about?
Do you believe in soulmates, or do you think true connections are more about how people grow together?
What nicknames do you secretly (or not-so-secretly) love being called?
What’s your favorite romantic book or story, and what kind of leading lady do you find most captivating in fiction? (I’ll try to be your type of fictional woman!)
I hope you don’t mind, but could you look me in the eyes and sing a few lines of a song for me?
Do you think couples should discuss engagement rings or proposal ideas before the big moment?
Have you ever imagined what our wedding day might look like, even just a little bit?
What’s one small thing I could do that you think would make our relationship even better?
When we talk, do you feel like I truly hear and understand what you’re saying?
Do you feel a strong sense of value and appreciation from me in our relationship?
What’s one way you’d really appreciate it if I expressed my love to you more often?

Spicy Questions To Ask Your Boyfriend

What’s the best thing you could possibly wake up to one morning, big or small?
If I were to leave you a little surprise note, what’s the perfect message you’d want it to say?
Do you prefer it when I make the first move, or do you like to be the one to surprise me?
If we found ourselves somewhere we probably shouldn’t be, would you still risk it for a kiss?
What’s one specific thing I do that you find to be a complete turn-on for you?
When it comes to showing affection in public, how do you feel about a little PDA
Do you enjoy getting spicy text messages from me?
What’s your absolute favorite kind of kiss we share?
When it comes to our relationship, do you prefer things to move fast and exciting, or do you like to take it slow and savor every moment?
Who’s a celebrity crush of yours that you find totally captivating?
When was the very first moment you started to feel attracted to me?
What’s a movie scene you’ve seen that you’d secretly love for us to recreate?
What’s one thing you’d love to whisper in my ear right now?
What’s one thing you’re a little nervous to tell me, but maybe want to share?
When we’re being intimate, do you prefer the lights on or off?
When it comes to physical touch, do you prefer kisses or hugs more, or is it a perfect blend?

Serious Questions To Ask Your Boyfriend

What qualities do you think are most important in a partner or spouse for a lasting connection?
How do you define a truly committed relationship?
Do you think we have a healthy level of emotional intimacy in our relationship?
Do you get jealous easily, or does it take a lot to stir that feeling in you?
What’s the longest relationship you’ve been in, and what did you learn from it?
Do you still keep in touch with any of your exes, and how do you feel about that?
What’s something I do that might bother you a little, that you’d be comfortable sharing?
What kind of parent do you hope to be someday, if you choose to have kids?
Would you ever sacrifice your career goals for love or a relationship?
Do you see yourself proposing to someone in the future, or perhaps being proposed to?
What are three things you’re really hoping to achieve this year in your personal or professional life?
Do you think I’m living up to my full potential right now?
What does your average workday look like for you?
Are you friends with your coworkers, or do you prefer to keep work and personal life separate?
Are you more of an introvert or an extrovert?
How do you typically handle anger when it comes up for you?
What do you usually do when you feel stressed or overwhelmed?
What’s your favorite part about being an adult?

Flirty Questions For Your Future Spouse

Do you remember what I was wearing on our very first date?
What’s your favorite physical thing about me?
What’s your favorite physical thing about yourself?
What’s your go-to, most comfortable cuddle position with me?
What do you like most about me now compared to when we first met?
What’s our favorite inside joke that only we understand?
Out of all the people in the world, what made you choose to be with me?
What’s your favorite way to be greeted by me when we see each other?
How many times did you want to ask me out before you actually did?
When we first kissed, what was that first kiss like for you?
Do you ever think about me during the day when we’re apart?
If I was feeling sad, how would you best make me feel better?
Do you like it when I wear perfume or cologne?
What color do you think I should wear more often, and why?
What’s something that still gives you butterflies when you think about our relationship?
Do you prefer kisses or hugs more?
Would you be willing to dance with me right now, just for fun?
Who’s your current celebrity crush?
What color do you associate me with, and why?
If you could describe our love in one word, what would it be?

Random Questions To Ask Your Boyfriend

What’s the craziest conversation you’ve ever accidentally overheard in public?
What’s your favorite smell in the whole world?
What was the last movie that actually made you cry?
What’s the most surprising musical artist you secretly love?
If you could pick up and move to an entirely new city, where would you go, and why?
If you didn’t have to work for a whole year, what would you do with all that free time?
What’s the weirdest habit you have that you think no one else does?
Have you ever used a pick-up line? If so, did it actually work?
If you could instantly adopt any skill without practicing, which one would you pick?
What’s one meal you wish you could cook perfectly?
What’s your go-to gas station snack combo when you’re on a road trip?
What was your favorite school lunch item as a kid?
Do you make your bed every morning?
Do you keep up with the news, or do you prefer to stay out of the loop?
If you could have any animal as a pet, even a mythical one, what would you choose?
If you could go back and relive any single day of your life, which one would it be and why?
What food or drink could you never live without?
What’s your biggest “hot take” – an unpopular opinion you strongly believe in?
Do you truly believe in aliens?
Do you think there are still sea creatures we haven’t discovered yet deep in the ocean?
Would you ever consider running for President (or Prime Minister, given our location)?
Do you ever find yourself “snooping” on people’s phones if you see them in public?
Would you go to space if you had the opportunity, even if it was risky?
Would you rather be right or be happy in an argument?
Do you prefer rainy days at home or sunny days at the beach?
What’s your comfort TV show – the one you always go back to?
What’s the best gift you’ve ever received?
What’s the best gift you’ve ever given someone?
What’s your favorite amusement park activity or ride?
What do you think is the best outfit in your closet right now?

Tips For Flirty Communication With Your Boyfriend

So, you want to keep that spark alive and make your boyfriend feel adored, right? It’s all about that playful, flirty vibe! Think of it like a fun little dance between the two of you.

Here are a few ways to keep that flirty communication flowing:

Compliment Your Partner

Instead of just “You look good,” try something like, “Wow, you’re really making that shirt look good today… almost too good.” Or, “I can’t stop thinking about how handsome you looked earlier.” It adds a little extra oomph and makes him feel genuinely seen and desired.

Tease Him Playfully

A little bit of teasing can be super flirty! If he messes up a word, you can playfully correct him with a wink emoji. Or if he’s being silly, you might say, “Oh, you’re just too charming when you’re being ridiculous.” It shows you’re paying attention and enjoying his quirks

Use Emojis in Text

Emojis are your friend here! A well-placed winky face , a smirking face , or even just a simple kissy face can convey a lot. You can also add a little “hehe” or “ooh la la” to a text to make it feel more mischievous.

Remember the Details

Bring up something specific he said or did that you found attractive. “I was just thinking about that thing you said last night, and it made me smile…” or “You were so strong when you did…., it was really hot.” It shows you’re listening and remembering.

Use His Name

Sometimes, just saying his name in a slightly softer or more emphasized way can be incredibly intimate and flirty, especially in person or on a call.

Suggest Future Fun

“I can’t wait to see you later… I have a feeling it’s going to be a good night.” Or, “What do you say we sneak away for a little bit this weekend?” It builds anticipation and hints at shared excitement.

Importance of Eye Contact

When you’re talking, especially about something playful or intimate, really hold his gaze. A prolonged look, a slight smile, or even a quick, intense glance can speak volumes without saying a word. It shows confidence and a deep connection.

Step Outside Your Comfort Zone (Just a Little!)

Flirting doesn’t have to be over-the-top. Sometimes, the sexiest thing is trying something new that feels a tiny bit daring for you, but still within your comfort zone. Maybe it’s a bolder compliment than usual, a more direct suggestion, or a touch that lingers a bit longer. Pushing your own boundaries just a little can make the interaction feel exciting and fresh for both of you.

Make Him Feel Special

When you’re feeling good about yourself, that confidence radiates and is incredibly attractive. Don’t be afraid to own your flirtiness!The main thing is to have fun with it and be genuine. Flirting is about making your boyfriend feel desired, special, and excited to be with you!

Conclusion

Hopefully, these questions will bring lots of laughter and good times for both of you. Asking these kinds of questions can also lead to really meaningful conversations, helping you both learn a lot about each other, about yourselves, and about your relationship in a fun and lighthearted way.

FAQs

What questions can I ask my boyfriend to make him smile?

What moment made you first realize you were falling for me?
If we could pause time and stay in one moment forever, which one would you choose?
What’s a little thing I do that always makes your heart feel full?
If we were characters in a love story, what would our title be?
What’s your favorite thing about being in love with me?
If you could plan a surprise romantic day for us, what would it include?
What song reminds you of us the most—and why?
When did you feel the closest to me, like nothing else mattered?
If love had a scent, what would “ours” smell like?
What’s one dream you have for our future that you’ve never told me?
What is your favorite thing we do together?
What do you see our future together looking like?
What is one thing about yourself you’ve never told me?
What made you decide you wanted to be with me?
What’s one thing you wish we did together more?
What do you think is most important in a relationship?
How have we influenced each other’s lives?
Do you think we would’ve dated in high school?
When did you first realize you loved me?
What’s your favorite part of being in a relationship?
Where would you want to get married?
Do you like surprise proposals or planned ones?
What was your first impression of me?
If I had to move for a job, would you come with me?
What are five words that describe me?
What’s something I do that you love but I don’t realize?
What is your love language?
What would be your go-to way to cheer me up?
What is your favorite restaurant we go to together?
What’s your idea of a perfect date?
If you could relive one day with me, which one would it be?
What’s one silly thing we’ve done together that still makes you laugh?
What’s something I do that always makes you feel loved?
If our relationship was a movie, what would the title be?
What’s one inside joke of ours you’ll never forget?
How do I make your life better without even trying?
If we could travel anywhere together, where would you take me?

How to Flirt Over Text ?

Flirting over text means being fun, kind, and a little playful.
You can start by giving a nice compliment or sharing a funny memory you both like.
You can also tease him a little in a friendly way.
Ask light questions like “Did you miss me today?” or “What would we be doing if I was with you right now?”
Keep the conversation natural—show that you care about what he says and don’t try too hard. The idea is to make him smile and enjoy talking to you.

Savvanah Blaze

Savvanah Blaze is a master of wit and humor, bringing sharp comebacks and clever roasts to every conversation. With a background in directing and writing comedic short films, she knows how to craft the perfect punchline. At GOOD ROAST, she shares the best funny roasts and witty replies for any situation, making sure you’re always ready with the perfect comeback.