How to Use These Questions
"Would you rather" is deceptively simple. Two options, one choice. But within that simplicity lies an incredible tool for learning about your partner. The best would-you-rather questions reveal values, priorities, fears, and desires in ways that direct questions often cannot. When your partner chooses between two hypothetical scenarios, they are telling you something real about who they are.
Use these questions during road trips, over dinner, waiting in line, or as part of your daily connection time. Apps like Sincerly also offer rotating question prompts if you want a curated experience. The only rule is to explain your choice after answering. The conversation that follows each question is where the real connection happens.
Do not rush through the list. Pick a handful at a time and let each question breathe. Some will lead to two-minute laughs. Others might spark an hour-long conversation about your future together.
Fun and Lighthearted Questions
- Would you rather always have to sing instead of speak or always have to dance instead of walk?
- Would you rather have a personal chef or a personal massage therapist for a year?
- Would you rather be able to talk to animals or speak every human language fluently?
- Would you rather give up coffee forever or give up dessert forever?
- Would you rather live in a treehouse or a houseboat?
- Would you rather always be slightly overdressed or slightly underdressed?
- Would you rather have the ability to fly or the ability to breathe underwater?
- Would you rather eat the same meal every day for a year or never eat the same meal twice?
- Would you rather be famous for something embarrassing or unknown for something amazing?
- Would you rather go camping in the mountains or relax on a tropical beach?
- Would you rather have unlimited free flights or unlimited free hotel stays?
- Would you rather have a rewind button for your life or a pause button?
- Would you rather always know what time it is or always know what the temperature is?
- Would you rather be able to cook any dish perfectly or play any instrument perfectly?
- Would you rather live in a world with no internet or no air conditioning?
- Would you rather have a magic fridge that is always full or a self-cleaning house?
- Would you rather win a lifetime supply of books or a lifetime supply of concert tickets?
- Would you rather be the funniest person in the room or the smartest?
- Would you rather live in a place with constant rain or constant sunshine?
- Would you rather have an extra hour every morning or an extra hour every evening?
- Would you rather be a morning person or a night owl for the rest of your life?
- Would you rather travel 100 years into the past or 100 years into the future?
- Would you rather only be able to whisper or only be able to shout?
- Would you rather have a pet dinosaur or a pet dragon?
- Would you rather eat only sweet food or only savory food for a month?
- Would you rather have the power of invisibility for a day or super speed for a day?
- Would you rather always have a full phone battery or always have a full gas tank?
- Would you rather live without music or live without movies?
- Would you rather have a perfect memory or the ability to forget anything on command?
- Would you rather explore outer space or the deep ocean?
Romantic and Relationship Questions
- Would you rather receive a love letter or a surprise date night?
- Would you rather have a big extravagant wedding or an intimate elopement?
- Would you rather relive our first date or our first kiss?
- Would you rather know exactly what I am thinking or have me always know what you are feeling?
- Would you rather spend every vacation together or each take one solo trip a year?
- Would you rather grow old in the city or in the countryside?
- Would you rather always go to bed at the same time or always wake up at the same time?
- Would you rather have a partner who is an amazing cook or an amazing dancer?
- Would you rather receive flowers every week or one grand romantic gesture a year?
- Would you rather have a shared hobby or respect each other's separate hobbies?
- Would you rather have a relationship where you never argue or one where you always resolve arguments quickly?
- Would you rather have a long engagement or a short one?
- Would you rather be surprised with a trip or help plan every detail together?
- Would you rather have a cozy night in every Friday or a date night out every Friday?
- Would you rather match outfits occasionally or never coordinate what you wear?
- Would you rather write vows together or keep them a surprise for each other?
- Would you rather receive a heartfelt voicemail or a long handwritten note?
- Would you rather always hold hands in public or always have your arms around each other?
- Would you rather recreate a favorite memory together or create a brand new one?
- Would you rather have a couple's tattoo or matching jewelry?
- Would you rather have breakfast in bed or dinner under the stars?
- Would you rather share passwords with each other or maintain digital privacy?
- Would you rather hear "I love you" or "I'm proud of you" more often?
- Would you rather have your partner plan all dates or take turns planning?
- Would you rather fall asleep cuddling or wake up cuddling?
- Would you rather your partner surprise you with a gift or ask what you want?
- Would you rather go on a double date or have a one-on-one date night?
- Would you rather your love story be turned into a movie or a book?
- Would you rather have a couple's bucket list of 10 items or 100 items?
- Would you rather renew your vows every decade or celebrate anniversaries in a new country each year?
Deep and Thought-Provoking Questions
- Would you rather always know when someone is lying or always get away with lying?
- Would you rather change one decision from your past or have a glimpse of your future?
- Would you rather lose all your memories from the past or be unable to make new memories?
- Would you rather be deeply respected or deeply loved?
- Would you rather have a long, simple life or a short, extraordinary one?
- Would you rather know how you die or when you die?
- Would you rather be the richest person in a poor country or a middle-class person in a wealthy country?
- Would you rather have the ability to change the past or see the future?
- Would you rather give up your greatest strength or fix your biggest weakness?
- Would you rather be admired by strangers or adored by family?
- Would you rather have a job you love that pays poorly or a job you hate that pays extremely well?
- Would you rather be forgiven or be understood?
- Would you rather have complete control over your emotions or complete control over your thoughts?
- Would you rather know the harsh truth or live in blissful ignorance?
- Would you rather be remembered for your kindness or your accomplishments?
- Would you rather have world peace for a decade or solve world hunger for a decade?
- Would you rather live a life with no regrets or a life with no fear?
- Would you rather experience everything once or master one thing completely?
- Would you rather lose the ability to read or the ability to speak?
- Would you rather be the most talented person at something nobody cares about or average at something everyone admires?
- Would you rather know the answer to every question or always ask the right question?
- Would you rather be completely self-sufficient or deeply connected to a community?
- Would you rather relive the happiest day of your life once a year or forget your worst memory entirely?
- Would you rather have universal respect but no close friendships, or deep friendships but be disliked by acquaintances?
- Would you rather confront an uncomfortable truth about yourself or maintain a comfortable illusion?
- Would you rather sacrifice your happiness for your partner's success or sacrifice your success for your partner's happiness?
- Would you rather spend a year apart knowing you would reunite stronger, or never be apart but remain the same?
- Would you rather understand every person's motives or have every person understand yours?
- Would you rather live without ambition or live without contentment?
- Would you rather be wise beyond your years or forever youthful in spirit?
Spicy and Playful Questions
- Would you rather your partner surprise you with a weekend getaway or a room makeover?
- Would you rather have an amazing first kiss with someone or an amazing last dance?
- Would you rather receive a slow massage or a spontaneous back hug from behind?
- Would you rather try a cooking class for two or a dance class for two?
- Would you rather be serenaded in public or have a private rooftop dinner?
- Would you rather play truth or dare with your partner or twenty questions?
- Would you rather wear your partner's favorite outfit for a day or have them wear yours?
- Would you rather recreate your partner's favorite movie scene or your own favorite?
- Would you rather have your partner write you a poem or compose you a song?
- Would you rather go skinny dipping in the ocean at night or swim under a waterfall?
- Would you rather have a partner who texts you sweet things all day or saves it all for when you are together?
- Would you rather be told you are attractive or told you are irresistible?
- Would you rather have a candlelit bath together or a sunrise picnic?
- Would you rather give your partner a full spa day or receive one yourself?
- Would you rather be kissed on the forehead or the back of the hand?
- Would you rather your partner plan a mystery date or tell you exactly what to expect?
- Would you rather your partner whisper something sweet in your ear in public or hold your face when they kiss you?
- Would you rather slow dance in the kitchen or stargaze on a blanket together?
- Would you rather have a partner who is boldly affectionate in public or reserved in public but intensely affectionate in private?
- Would you rather exchange love letters once a month or have a dedicated couple's photo shoot once a year?
Life Decisions and Future Questions
- Would you rather live in your dream home in a place you dislike or an average home in your dream location?
- Would you rather have two kids or four pets?
- Would you rather retire early with less money or work longer and retire wealthy?
- Would you rather prioritize career growth or work-life balance for the next five years?
- Would you rather live close to family or have complete independence far away?
- Would you rather spend money on experiences or on things?
- Would you rather raise kids in the city or in a small town?
- Would you rather own a business together or keep your professional lives completely separate?
- Would you rather homeschool your children or send them to private school?
- Would you rather move to a new country every five years or stay in one place your entire life?
- Would you rather have a large circle of acquaintances or a small circle of deep friendships?
- Would you rather save aggressively and retire at 50 or live comfortably and retire at 65?
- Would you rather have a home with a big kitchen or a big backyard?
- Would you rather be known as the fun couple or the wise couple among your friends?
- Would you rather volunteer together regularly or donate money to causes you care about?
- Would you rather take sabbaticals from work to travel or save vacation days for one epic trip?
- Would you rather leave an inheritance for your children or spend it creating family memories?
- Would you rather drive cross-country together or take a cruise?
- Would you rather have matching retirement hobbies or totally different ones?
- Would you rather build your own home from scratch or renovate a historic property together?
Daily Life and Quirky Questions
- Would you rather always do the cooking or always do the dishes?
- Would you rather share a closet or share a bathroom counter?
- Would you rather your partner steal the blankets or snore quietly?
- Would you rather grocery shop together or divide and conquer the list?
- Would you rather always agree on what to watch or always agree on where to eat?
- Would you rather share one car or have two separate cars?
- Would you rather have a joint bank account or keep finances completely separate?
- Would you rather hire a cleaner or split all chores exactly 50/50?
- Would you rather always have fresh flowers in the house or always have scented candles burning?
- Would you rather eat takeout three times a week or cook every meal at home?
- Would you rather have the thermostat set to your partner's preference or yours?
- Would you rather handle all the finances or handle all the social planning?
- Would you rather adopt a pet together or start a garden together?
- Would you rather binge a series together (no watching ahead) or have separate shows?
- Would you rather have a home gym or a home theater?
- Would you rather always pick the restaurant or always pick the movie?
- Would you rather share a toothbrush in an emergency or share deodorant?
- Would you rather live in a spotless minimalist home or a cozy cluttered one?
- Would you rather wake up to your partner making breakfast or come home to them making dinner?
- Would you rather have your partner fold the laundry or put it away?
These questions are just the beginning. The best conversations happen when one question leads to another that neither of you planned. Use Sincerly to get fresh daily prompts that keep the discovery going long after you have worked through this list.