One of the best date nights my partner and I stumbled upon wasn’t planned, fancy, or even outside the house. It was just us, a couple of drinks, and an idea I found while scrolling online: a huge list of “Would You Rather” questions for couples.
Some were funny, some went deep, and others… well, they got spicy fast. But by the end of it, we’d uncovered things about each other that we’d never talked about before.
It was surprising, funny, and even a little uncomfortable, but mostly it was just honest. And it reminded us why taking time to just listen and laugh together still matters, no matter how long you’ve been together.
This list takes things up a notch. You’ll find questions that cover everything from awkward “what ifs” to wild fantasies and deep, emotional topics. Try them out on a quiet night, or save them for when you need something new to spark conversation.
These aren’t your usual icebreakers—they’ll challenge you, push some boundaries, and guarantee you’ll end up a little closer by the time you reach the last one.
Flirty and Playful Starters
- have a wild makeout session in public or a long, slow kiss behind closed doors?
- have a secret “code” for flirting in public or a private song that only you two know the meaning of?
- have a 24-hour challenge where you can only communicate through touch or one where you can only communicate through looks?
- be caught having a private moment or hear a stranger talking about you?
- have a passionate night in a luxury hotel or a cozy evening at home with no interruptions?
- get a flirty message every hour from your partner or have a secret admirer send you anonymous love notes?
- sneak away during an event for a quick kiss or wait till you get home and make the moment last?
- your partner always kiss you passionately or hold your hand no matter where you are?
- have your partner make the first move every time or surprise them by doing it yourself?
Also, check out some authentic ways to say “Thank You” and express appreciation.
Going All In on Intimacy
- spend a night focused on each other’s fantasies or a night full of surprises?
- be blindfolded or handcuffed by your partner (if they choose to)?
- talk about every detail of your wildest dream or leave some things mysterious?
- shower together every day or have a rule where you can only touch at certain times?
- receive a back massage or give one in the dark?
- have a private day at the beach with nobody around or a night by a fireplace at a secluded cabin?
- spice things up with a fun game or take it slow and romantic every time?
- have a random flirty text every day or a surprise voice message?
Romantic Risks and Adventure Would You Rather Questions
- take a spontaneous trip with only one hour to pack or plan an elaborate getaway?
- have a late-night swim under the stars or dance alone together at sunrise?
- sleep under the stars with no tent or spend the night in a luxury tent with all the comforts?
- be able to explore a haunted house together or a famous underground tunnel?
- have a secret vacation spot only the two of you know or a favorite table at a famous restaurant?
- stay up all night talking about life or spend the whole day in silence but by each other’s side?
- give each other surprise kisses or randomly hold each other’s hand?
For the Bold and Uninhibited Would You Rather Questions
- have a night where you only communicate through actions or a night where you only communicate through whispers?
- spend the night under the stars or the whole day locked in together?
- let your partner pick out an outfit for you or pick one out for them?
- roleplay your favorite movie scene or create a story of your own?
- dance in the rain or swim under a waterfall?
- have a full day of just kissing or a full day of whispers and flirting without touch?
Pushing Boundaries Would You Rather Questions
- have an “open secrets” rule where you both share every thought or “secret fantasies” where each reveals a hidden desire?
- spend a day watching each other’s favorite movies or a night in the dark only talking?
- talk openly about every part of your past or promise to only look forward together?
- try something totally new together or stick with what you know?
- be together all day but no physical contact or only meet at night and make the most of it?
Wild What-Ifs
- win the lottery but have to keep it a secret or be famous but anonymous to everyone?
- spend a day reading each other’s minds or be invisible for a night together?
- live a month in each other’s bodies or a month with each other’s thoughts?
- always know what the other is thinking or never know at all?
- be able to shape-shift into anything your partner likes or read their mind?
For the Fantasy Lovers Would You Rather Questions
- have a love story like a movie or one that feels like a fairy tale?
- be able to freeze time for moments with each other or fast-forward to your next big adventure?
- be each other’s first everything or each other’s last everything?
- share a dance in the rain or under a full moon?
- write a book together or record a song together?
Deep Thoughts Would You Rather Questions
- know every part of each other’s past or be content with just the present?
- be able to see a part of your partner’s future or forget one moment from the past?
- share your biggest fear or your biggest secret?
- spend forever only with your partner or have everyone in your life but be limited with each other?
- be able to hear each other’s thoughts or only feel each other’s emotions?
For the Adventurous Souls Would You Rather Questions
- skinny-dip together in a secluded spot or have a private night by the fireplace in a cabin?
- go on a road trip with only a single bag each or stay at a luxury resort but be confined to the grounds?
- spend a night lost in the wilderness together or be locked in a luxury suite with no phones or internet?
- experience every romantic spot around the world or every thrill-seeking adventure?
- be stranded on an island with each other or on a mountain top?
- have a midnight hike under the stars or a sunrise swim at a hidden beach?
- stay in an off-grid cabin together or a glasshouse hotel room in a busy city?
- live on the road in a cozy van or travel around in luxury hotels?
- spend a night under the Northern Lights or at a private beach house?
- have a yacht to explore the ocean or a treehouse to explore the forest?
Spice and Tease Would You Rather Questions
- have a night of nonstop teasing or a day of flirting with no touch allowed?
- play a game where you can’t look at each other or one where you can’t talk?
- leave little surprises for each other or only communicate through touch for a whole day?
- share all your fantasies or keep some things mysterious?
- write down a secret desire and let your partner discover it or have them whisper one in your ear?
- spend a day on a private yacht or a night in a luxury hot tub?
- be locked in together for 24 hours or have to communicate only through texts?
- take turns being in control or let things happen spontaneously?
- receive a slow back massage or give one?
- plan a mystery date or let your partner plan one for you?
Private Confessions Would You Rather Questions
- share your most private thoughts with each other or a diary with only hints?
- talk openly about every past relationship or never discuss them again?
- be open about every fantasy or have some left unexplored?
- get caught sneaking kisses or caught sneaking out together?
- be honest about everything or let a few things stay private?
- share your phone password or have no secrets but no access to each other’s phones?
- get embarrassed in front of each other or in front of friends?
- laugh uncontrollably in an intimate moment or accidentally say something awkward?
- hear each other’s awkward stories or each other’s favorite memories?
- only talk about your dreams or your fears?
The Deep and Personal Would You Rather Questions
- know your partner’s happiest memory or their most painful one?
- forgive every mistake or never be hurt in the first place?
- have all your arguments resolved immediately or never argue at all?
- be able to read each other’s emotions or know each other’s thoughts?
- always feel comforted or always feel loved?
- give up on a past regret or learn a lesson from it?
- understand each other without words or never misunderstand each other?
- relive a favorite moment together or rewrite a mistake?
- have one secret kept between you or know absolutely everything?
- find out everything about each other’s pasts or focus only on the future?
Daring and Challenging Would You Rather Questions
- go through each other’s phones or each other’s photo albums?
- reveal a past mistake or hear about theirs?
- stay silent when you’re upset or share every frustration?
- try every new thing your partner suggests or have them try what you want?
- accept every dare from each other or never dare each other again?
- take a vow of honesty or a vow of loyalty?
- share a vulnerable moment or only show your strongest side?
- have a relationship with no secrets or one with total trust?
- confess to your biggest insecurity or hear your partner’s?
- have your partner always know when you’re upset or never know at all?
Emotional Depths Would You Rather Questions
- comfort each other in person every time or talk it through over text when needed?
- be your partner’s first love or their last love?
- have a perfect memory of every moment together or cherish just a few?
- share every moment of sadness or keep it to yourself to protect them?
- love deeply and risk heartbreak or never love deeply but always stay safe?
- grow and change together or stay exactly the same forever?
- hear every little thing your partner loves about you or feel it in their actions?
- only hear “I love you” when it’s most needed or hear it every day?
- be there for each other in every big moment or never miss a single small one?
- talk out every misunderstanding or move on and forgive?
Taking It to the Next Level Would You Rather Questions
- have one night where you tell each other absolutely everything or one where you share nothing at all?
- spend a night where you can’t touch at all or one where you can only communicate by touch?
- always be the one making the first move or let your partner make it every time?
- plan every date night or be surprised every single time?
- have a no-phone rule on dates or only talk over the phone?
Fantasy and Dream Life Would You Rather Questions
- have a dream home on a private beach or a luxury cabin in the mountains?
- live in a world where you can teleport anywhere together or one where you can read each other’s thoughts?
- have a personal chef or a private masseuse?
- explore space together or the deepest parts of the ocean?
- live in a bustling city penthouse or a secluded country estate?
- win the lottery together or inherit a private island?
- discover hidden treasure with your partner or uncover a lost city?
- live in a romantic comedy or an action movie with your partner?
- only travel together or only work together?
- go on endless adventures or stay home and create the coziest sanctuary?
Bold Relationship Risks Would You Rather Questions
- reveal your wildest fantasy or hear your partner’s?
- spend a month apart or spend a month with no physical affection?
- always be the one to apologize or never apologize at all?
- stay together in every lifetime or experience a new love in each one?
- always be the one planning your dates or leave it entirely up to your partner?
- open up fully about every fear or keep some things mysterious?
- have the ability to change each other’s minds or influence each other’s emotions?
- each keep a big secret or have no secrets at all?
- know your partner’s every weakness or reveal yours first?
- discuss every detail of your future together or let it unfold naturally?
Personal Boundaries and Trust Would You Rather Questions
- share every location with your partner or have them share their location only when needed?
- never be able to lie to each other or never be able to read each other’s minds?
- take a lie detector test together or share your phone password?
- know about every past relationship or agree not to discuss them at all?
- have total trust or always be reassured of each other’s love?
- your partner never lie to you about anything or keep certain things to themselves?
- feel complete honesty every day or feel total loyalty without question?
- talk openly about exes or pretend they never existed?
- hear every compliment your partner receives from others or never hear about it?
- only ever hear the truth or have moments of comforting white lies?
Spicy Fantasies and Secrets Would You Rather Questions
- try something completely out of the norm together or stick with what’s familiar?
- keep a secret fantasy to yourself or share it, even if it surprises your partner?
- only have romantic dates in public or only in private?
- be open about every thought or only share when asked?
- get an anonymous love letter from your partner or a surprise message every day?
- tell your partner one big secret or hear one from them?
- share your most vulnerable moment or your proudest one?
- make every intimate moment spontaneous or plan each one?
- roleplay your own love story or a famous romantic movie scene?
- share all your romantic dreams or keep some things just for yourself?
Embarrassing But Fun Would You Rather Questions
- accidentally walk in on each other or have someone walk in on you?
- confess to something embarrassing or hear an embarrassing confession?
- snore every night or talk in your sleep?
- be caught singing in the shower or dancing around the house?
- accidentally text your partner something embarrassing or post it publicly?
- relive an awkward date or retell a funny story from one?
- have an embarrassing photo go viral or an awkward video?
- be the one caught sleeping at a party or the one who says something embarrassing?
- be caught talking in your sleep or sleepwalking?
- laugh uncontrollably during a serious moment or get the giggles in a romantic one?
As you think about these fun questions, it’s also important to recognize the green flags in a relationship that signify a healthy partnership. Check out our post on green flags in a relationship for insights that can enhance your love story.
Financial Fantasies Would You Rather Questions
- have your partner spoil you with gifts or surprise you with experiences?
- live debt-free or live with unlimited spending money for a year?
- win a million dollars together or receive an annual salary forever?
- have a dream job with little pay or an okay job with high pay?
- invest in a property together or buy a luxury car?
- save for retirement together or splurge on adventures?
- have a high-stress, high-paying job or a low-stress, low-paying one?
- become a millionaire but never retire or live comfortably and retire early?
- start a business together or invest in a shared passion?
- build a charity organization or fund your dream lifestyle?
Just Plain Fun Would You Rather Questions
- throw a costume party together or a dance party?
- spend a day at an amusement park or a water park?
- have a cooking competition at home or a scavenger hunt?
- play a board game every night or a card game?
- have a weekly date night or a monthly getaway?
- go to a concert or have a private music session at home?
- dance around the house to your favorite song or sing along to a cheesy tune?
- go to a comedy show or a live theater performance?
- watch a horror movie together or a classic romantic film?
- go to a trivia night or an escape room?
Travel Dreams Would You Rather Questions
- go to a tropical island or a snowy mountain resort?
- take a road trip across the country or fly to a new destination every month?
- visit every major city in the world or every small hidden town?
- travel in an RV for a year or stay in luxury hotels?
- live in a different country each year or settle in one dream location?
- backpack across Europe or go on a guided tour through Asia?
- explore ancient ruins or futuristic cities?
- go on a luxurious cruise or a rugged camping trip?
- spend a year traveling together or settle in one place and explore every detail?
- travel with no budget or work while you travel?
Nostalgia and Memories
- relive your first date or experience a new one together?
- see photos from each other’s childhood or hear the stories?
- visit your partner’s hometown or show them yours?
- have an old photo album or a new one you build together?
- relive one happy memory or have the power to erase a bad one?
- keep a sentimental item or a keepsake from your travels?
- watch each other’s favorite childhood movies or listen to their favorite songs?
- share your earliest memory or your favorite one from your teens?
- keep every gift you’ve given each other or one important memory?
- write down your love story or make a photo book?
Passionate and Romantic Would You Rather Questions
- receive a surprise romantic letter every month or a spontaneous romantic date?
- only be able to kiss each other on the weekends or only hold hands on weekdays?
- surprise each other with small gifts or secret gestures of love?
- have a candlelit dinner every night or always eat in front of a cozy fire?
- be able to kiss your partner anytime, anywhere, or only have one long kiss each day?
- go on a mystery getaway together or have a fancy staycation?
- have endless romantic nights or endless fun, playful days?
- celebrate each anniversary in a new city or return to the same special spot?
- receive love letters each week or a long, handwritten letter once a year?
- relive your first kiss or create a new special memory together?
Real-Life Choices
- give up your favorite hobby for a year or see your partner give up theirs?
- spend a year without social media or without Netflix?
- spend every holiday with family or just the two of you every time?
- work at your dream job or be a stay-at-home partner while the other works?
- wake up early every day together or stay up late every night together?
- go vegetarian together or give up all sweets?
- have an open-door policy at home or complete privacy?
- handle all the cooking or all the cleaning for the household?
- share all of your passwords or keep a few things private?
- live in a big city or a small town forever?
Future Planning Would You Rather Questions
- live a minimalist lifestyle together or go for complete luxury?
- save every penny for your dream home or spend it on travel?
- start a business together or work completely separate careers?
- retire in your hometown or move to a new country?
- invest in a big house or create a small, cozy home?
- buy a fixer-upper together or a ready-to-live-in home?
- take a chance on a risky investment or stay financially conservative?
- live debt-free or own multiple properties?
- spend on memorable experiences or valuable possessions?
- achieve career success first or build a family first?
Hypotheticals and Wild Choices
- live with unlimited wealth but no personal privacy or have a modest life with full privacy?
- be famous and loved by all or only known and loved by each other?
- have the ability to pause time or speed up only the boring parts?
- control your dreams or see your partner’s dreams?
- live in a world where no one lies or a world where you always know when someone lies?
- live in a world with only music or only art?
- always have to tell the truth or always be silent about sensitive things?
- be a hero for a day or be unknown but save many lives?
- see how others see you or see how your partner sees you?
- live in a world without conflict or one without any secrets?
Emotional Depths
- cry every time you’re truly happy or laugh every time you’re sad?
- never get jealous or never feel guilty?
- always forgive but never forget, or always forget but never fully forgive?
- understand every emotion or only the emotions of the person you love most?
- share each other’s stress or take turns comforting each other?
- love passionately but feel heartbreak, or feel steady love with no intense highs or lows?
- be a calming influence for your partner or an exciting one?
- live in complete peace or always experience the thrill of romance?
- experience every emotion deeply or live content and undisturbed?
- be deeply loved but misunderstood, or well understood but never deeply loved?
Just for Laughs
- dress up in silly costumes every holiday or match outfits once a month?
- get caught singing in the car or dancing when no one’s watching?
- have a pet parrot that repeats everything or a pet monkey that causes mischief?
- wear matching pajamas to every party or accidentally wear pajamas to a fancy dinner?
- always have food in your teeth or a noticeable stain on your shirt?
- accidentally trip on a date or say something totally awkward?
- be the one who snores or the one who sleep-talks?
- accidentally burp at a serious moment or hiccup uncontrollably on a first date?
- be known for your laugh or your sense of humor?
Final Round
- love with complete abandon or be in control at all times?
- share every dream together or keep some dreams private?
- know each other’s every future plan or leave some things unknown?
- always know how to comfort each other or always make each other laugh?
- your partner always know what’s on your mind or have some mystery left?
- be able to see the rest of your love story or live it one day at a time?
Final Thoughts
Going through these questions, you might feel like you’ve uncovered a whole new side of your relationship, or maybe you just laughed harder than usual and found some ridiculous, unexpected things about each other.
Either way, these questions go beyond small talk and usual topics, and that’s where the fun happens.
It’s easy to get comfortable and skip the bigger or stranger conversations, but when you let yourself go there, you realize there’s so much more to discover, even after years together.
Whether you saved the bolder questions for later or started with the deep stuff, this list is about getting closer, laughing hard, and showing each other that there’s always more to explore.
Whenever things feel routine or you just want a change, come back to these questions or make up some of your own. Real talk, laughs, and a few surprises? Not a bad way to spend an evening.
