300 Would You Rather Questions for Your Boyfriend

Relationships are all about the little moments—those silly conversations, playful debates, and the times when you both crack up over the most random topics.

If you’re looking to spice up your chats or dig a little deeper into your boyfriend’s quirks, Would You Rather questions are the way to go. They’re fun, they’re flirty, and sometimes, they’ll leave you questioning his choices (like, really? No pizza for a year?).

Whether you want to keep things light or dive into deeper territory, these questions are perfect for any mood. Plus, they’re a great excuse to spend more time laughing, bonding, or even playfully teasing each other.

So grab a snack, get comfy, and let’s kick off the ultimate Would You Rather session with your favorite person!

Best Would You Rather Questions

1. Would you rather always be 10 minutes late or 20 minutes early?
2. Would you rather have unlimited money or unlimited free time?
3. Would you rather live in a mansion in the city or a cozy cabin in the mountains?
4. Would you rather give up your smartphone or your favorite food?
5. Would you rather explore space or the deepest parts of the ocean?
6. Would you rather always know the truth or never know it at all?
7. Would you rather travel the world for free or have $1 million to spend however you like?
8. Would you rather be able to talk to animals or speak every human language?
9. Would you rather lose all your memories from before today or never make new ones?
10. Would you rather have a job you love for little money or one you hate for a lot of money?
11. Would you rather be famous but always in the spotlight or unknown and peaceful?
12. Would you rather have the ability to teleport or to read minds?
13. Would you rather live in a world without music or without movies?
14. Would you rather be the funniest person in the room or the smartest?
15. Would you rather find true love or win the lottery?
16. Would you rather live 100 years in the past or 100 years in the future?
17. Would you rather always have to sing everything you say or dance everywhere you go?
18. Would you rather only eat sweet foods or savory foods for the rest of your life?
19. Would you rather be able to pause time or rewind it?
20. Would you rather be invisible for a day or fly for a day?
21. Would you rather have a rewind button or a fast-forward button for your life?
22. Would you rather have no internet for a year or no vacations for a year?
23. Would you rather live in a world where everyone tells the truth or where everyone lies?
24. Would you rather always have great hair or perfect teeth?
25. Would you rather never be able to cry or never be able to laugh?

Related: 300 Would You Rather Questions [Spice Things Up!]

Romantic Would You Rather Questions

1. Would you rather have a long-distance relationship or live together in a small apartment?
2. Would you rather have a romantic dinner at home or a fancy restaurant?
3. Would you rather receive a heartfelt letter or an expensive gift?
4. Would you rather always celebrate anniversaries or never forget special dates?
5. Would you rather plan a dream wedding or elope somewhere spontaneous?
6. Would you rather have a partner who’s overly romantic or one who rarely shows affection?
7. Would you rather spend a week on a tropical island with me or in a cozy winter cabin?
8. Would you rather slow dance in the living room or under the stars?
9. Would you rather relive our first date or create a new unforgettable moment together?
10. Would you rather cuddle all night or hold hands all day?
11. Would you rather watch a sunset together or a sunrise?
12. Would you rather surprise me with a gift or plan a surprise date?
13. Would you rather always celebrate Valentine’s Day or skip it for something unique?
14. Would you rather have a partner who loves to cook or one who loves to clean?
15. Would you rather be loved deeply by me or be admired by everyone else?
16. Would you rather have a fairy-tale romance or a solid, real-world partnership?
17. Would you rather be my first love or my last?
18. Would you rather kiss me in the rain or hug me in the snow?
19. Would you rather write a song about me or paint a picture of us?
20. Would you rather share your biggest secret or know mine?
21. Would you rather go on a spontaneous road trip or a carefully planned vacation?
22. Would you rather have a partner who loves grand gestures or small everyday acts?
23. Would you rather spend a quiet night talking or go out for an exciting adventure?
24. Would you rather make each other laugh or make each other cry (happy tears)?
25. Would you rather grow old together or stay young forever with me?

Funny Would You Rather Questions

1. Would you rather have a head the size of a watermelon or the size of a tennis ball?
2. Would you rather fight one horse-sized duck or 100 duck-sized horses?
3. Would you rather always smell like garlic or always smell like wet socks?
4. Would you rather eat a bowl of bugs or sleep in a room full of spiders?
5. Would you rather never stop hiccuping or sneezing every five minutes?
6. Would you rather have spaghetti for hair or waffles for feet?
7. Would you rather only be able to whisper or only be able to shout?
8. Would you rather have to wear clown shoes every day or a clown wig?
9. Would you rather always laugh at inappropriate times or cry uncontrollably in serious moments?
10. Would you rather lose your eyebrows or your eyelashes?
11. Would you rather wear the same outfit every day or never wear the same thing twice?
12. Would you rather always speak in rhymes or only speak in riddles?
13. Would you rather have to dance everywhere you go or sing every word you say?
14. Would you rather eat only ketchup or only mustard for a year?
15. Would you rather be a superhero with an embarrassing costume or a villain with style?
16. Would you rather have a pet that talks or one that reads minds?
17. Would you rather burp loudly every time you kiss or fall asleep every time you hug?
18. Would you rather be able to only walk backward or crawl everywhere?
19. Would you rather be constantly sticky or always itchy?
20. Would you rather have your dream job but work with your worst enemy or a boring job with your best friend?
21. Would you rather live in a house made of candy or one made of ice?
22. Would you rather have a talking dog or a flying cat?
23. Would you rather have no nose or no ears?
24. Would you rather eat ice cream with ketchup or pizza with chocolate sauce?
25. Would you rather be the star of a bad movie or the extra in a great one?

Deep Would You Rather Questions

1. Would you rather know how the world began or how it will end?
2. Would you rather be loved by everyone but never feel it or love deeply but never be loved back?
3. Would you rather have the power to change the past or see into the future?
4. Would you rather live a simple life with few worries or a complicated life full of achievements?
5. Would you rather always speak your mind or never speak at all?
6. Would you rather spend your life searching for meaning or accept that life is meaningless?
7. Would you rather save one loved one or save 100 strangers?
8. Would you rather find the cure to a deadly disease or solve world hunger?
9. Would you rather live without regret or without fear?
10. Would you rather always feel guilty or always feel lonely?
11. Would you rather have unlimited knowledge or unlimited power?
12. Would you rather lose all your loved ones or lose all your memories of them?
13. Would you rather die knowing you made a difference or live a long, uneventful life?
14. Would you rather forgive someone who deeply hurt you or hold onto the grudge forever?
15. Would you rather live a lie to stay happy or face a painful truth?
16. Would you rather have clarity of mind or peace in your heart?
17. Would you rather sacrifice your happiness for someone else or let them sacrifice theirs for you?
18. Would you rather discover your true purpose or realize life has no set purpose?
19. Would you rather explore the universe or understand the depths of your own mind?
20. Would you rather never experience sadness or never experience anger?
21. Would you rather have all the answers or all the questions?
22. Would you rather achieve all your goals but lose all your relationships or keep your relationships but lose your goals?
23. Would you rather know your exact time of death or live with uncertainty?
24. Would you rather create something that changes the world or someone’s life?
25. Would you rather be remembered by history or loved in the present?

Flirty Would You Rather Questions

1. Would you rather cuddle for an hour or kiss for five minutes?
2. Would you rather have me whisper sweet things in your ear or kiss your neck?
3. Would you rather go on a surprise date or plan one together?
4. Would you rather be called handsome or hot?
5. Would you rather dance with me in public or keep it private?
6. Would you rather have a spontaneous kiss or a long, planned one?
7. Would you rather send flirty texts all day or talk face-to-face?
8. Would you rather compliment me on my looks or my personality?
9. Would you rather hold hands in public or keep it subtle?
10. Would you rather see me dressed casually or all dressed up?
11. Would you rather give me a massage or get one from me?
12. Would you rather stay in and have a cozy night or go out for a fancy dinner?
13. Would you rather kiss under fireworks or under the stars?
14. Would you rather tease me or be teased by me?
15. Would you rather always know what I’m thinking or keep some mystery alive?
16. Would you rather get a flirty surprise text or an unexpected call?
17. Would you rather kiss on the cheek or the forehead?
18. Would you rather compliment my eyes or my smile?
19. Would you rather hold me close or let me make the first move?
20. Would you rather go on a sunset walk or watch a romantic movie together?
21. Would you rather have a long hug or a short, passionate kiss?
22. Would you rather spend time laughing together or gazing into each other’s eyes?
23. Would you rather hear me say “I love you” or write it to you?
24. Would you rather flirt through a game or over dinner?
25. Would you rather kiss in the rain or in the snow?

Date Night Would You Rather Questions

1. Would you rather have a candlelight dinner or a picnic under the stars?
2. Would you rather cook a meal together or order in from our favorite restaurant?
3. Would you rather go to the movies or binge-watch a series at home?
4. Would you rather take a dance class together or try a couple’s yoga session?
5. Would you rather go bowling or play mini-golf?
6. Would you rather spend the evening stargazing or watching a sunset?
7. Would you rather have a spontaneous adventure or a carefully planned date?
8. Would you rather go for a romantic drive or take a walk along the beach?
9. Would you rather share a dessert or have one each?
10. Would you rather visit a fancy restaurant or a cozy diner?
11. Would you rather go for a late-night ice cream run or get hot chocolate?
12. Would you rather play board games or try a virtual reality experience?
13. Would you rather go to a comedy show or watch live music?
14. Would you rather dress casually for a date or go all out?
15. Would you rather try something new together or revisit a favorite spot?
16. Would you rather plan a date for me or have me plan one for you?
17. Would you rather go on a day trip or spend a quiet evening at home?
18. Would you rather explore a new city or discover hidden gems in our own?
19. Would you rather take a cooking class together or learn a new hobby?
20. Would you rather spend the night talking or playing games together?
21. Would you rather go to a rooftop bar or a quiet café?
22. Would you rather spend the night people-watching or taking couple selfies?
23. Would you rather attend a wine tasting or explore a farmer’s market?
24. Would you rather plan a surprise for me or be surprised by me?
25. Would you rather have a cozy movie marathon or a karaoke night at home?

Spicy Would You Rather Questions

1. Would you rather kiss me for 10 minutes or hug me for an hour?
2. Would you rather whisper sweet nothings or shout your love for me?
3. Would you rather explore new places together or explore new things in the bedroom?
4. Would you rather have a steamy night in or a bold adventure out?
5. Would you rather blindfold me or be blindfolded by me?
6. Would you rather play a romantic truth-or-dare game or share fantasies?
7. Would you rather kiss me passionately or cuddle for hours?
8. Would you rather surprise me with something intimate or have me surprise you?
9. Would you rather spend a weekend away in a luxury hotel or a secluded cabin?
10. Would you rather go skinny-dipping or have a midnight swim?
11. Would you rather get caught in a passionate moment or sneak one in public?
12. Would you rather tease me or let me take control?
13. Would you rather share a romantic secret or hear mine?
14. Would you rather spend the evening watching a romantic movie or making one of our own?
15. Would you rather have breakfast in bed or a midnight snack together?
16. Would you rather kiss me in a daring location or somewhere cozy?
17. Would you rather explore something new or perfect something we’ve tried?
18. Would you rather plan a night full of surprises or know what’s coming?
19. Would you rather wear something daring for me or see me wear something daring for you?
20. Would you rather have a secret date night or share it with close friends?
21. Would you rather hear a flirty compliment from me or give me one?
22. Would you rather take charge or have me lead the way?
23. Would you rather spend the night holding hands or letting go of inhibitions?
24. Would you rather express love through words or actions?
25. Would you rather share a kiss under fireworks or in a quiet, intimate moment?

Juicy Would You Rather Questions

1. Would you rather reveal your most embarrassing moment or hear mine?
2. Would you rather confess your biggest crush before me or keep it a secret?
3. Would you rather share your search history or read mine?
4. Would you rather talk about an ex or never discuss the past at all?
5. Would you rather know my guilty pleasure or share yours?
6. Would you rather tell me your most awkward date story or hear mine?
7. Would you rather admit to a hidden talent or a hidden fear?
8. Would you rather share your biggest regret or your proudest moment?
9. Would you rather hear my wildest story or tell me yours?
10. Would you rather have a serious talk about the past or dream about the future?
11. Would you rather admit to stalking someone online or know if I have?
12. Would you rather spill a secret about yourself or guess one about me?
13. Would you rather ask me a daring question or answer one?
14. Would you rather talk about your first love or your worst heartbreak?
15. Would you rather hear about my wildest adventure or share yours?
16. Would you rather admit to a bad habit or point out mine?
17. Would you rather read my diary (if I had one) or let me read yours?
18. Would you rather share a fantasy or hear one of mine?
19. Would you rather reveal a lie you’ve told me or hear one I’ve told you?
20. Would you rather confess a white lie or hear one?
21. Would you rather discuss a mistake you’ve made or a lesson you’ve learned?
22. Would you rather talk about your biggest insecurity or your greatest strength?
23. Would you rather gossip about friends or share a secret about family?
24. Would you rather answer a deep question truthfully or skip it entirely?
25. Would you rather have a totally honest talk or keep things mysterious?

Cute Would You Rather Questions

1. Would you rather hold hands all day or share a cozy blanket?
2. Would you rather wake up to my good morning text or a surprise breakfast?
3. Would you rather plan a date for me or have me plan one for you?
4. Would you rather have matching outfits or matching tattoos?
5. Would you rather watch cartoons together or build a pillow fort?
6. Would you rather slow dance in the living room or under the stars?
7. Would you rather have a pet together or care for a plant together?
8. Would you rather surprise me with a small gift or a sweet note?
9. Would you rather bake cookies together or decorate cupcakes?
10. Would you rather take a couple of selfies or have someone take our pictures?
11. Would you rather share your ice cream or get one for me?
12. Would you rather have a cute nickname for me or give me one?
13. Would you rather feed me bites of food or be fed by me?
14. Would you rather take care of me when I’m sick or have me take care of you?
15. Would you rather cuddle under a blanket or sit by the fire together?
16. Would you rather plan a cute date or surprise me with one?
17. Would you rather spend the day in matching pajamas or dressed up?
18. Would you rather make a playlist for me or receive one from me?
19. Would you rather write me a love letter or draw me a picture?
20. Would you rather have a spontaneous hug or a surprise kiss?
21. Would you rather spend a lazy Sunday together or an exciting Saturday?
22. Would you rather pick out matching mugs or matching T-shirts?
23. Would you rather write me a song or sing me one?
24. Would you rather do a silly dance with me or playfully prank me?
25. Would you rather laugh at my jokes or make me laugh at yours?

Relationship Would You Rather Questions

1. Would you rather always text or always call each other?
2. Would you rather go on double dates or keep dates private?
3. Would you rather have similar personalities or complementary ones?
4. Would you rather be the one to say sorry or wait for me to apologize?
5. Would you rather spend all day together or have time apart?
6. Would you rather face challenges as a team or solve them individually?
7. Would you rather know my thoughts or let me surprise you?
8. Would you rather celebrate every milestone or keep them simple?
9. Would you rather travel together or stay home and make memories?
10. Would you rather take a class to learn something new together or teach each other skills?
11. Would you rather have shared hobbies or separate ones?
12. Would you rather plan a big future together or take it day by day?
13. Would you rather resolve arguments quickly or take time to cool off?
14. Would you rather laugh through tough times or cry together?
15. Would you rather make decisions together or trust me to take the lead?
16. Would you rather share everything with me or keep some things private?
17. Would you rather spend time with my family or your own?
18. Would you rather always compromise or stand firm on your beliefs?
19. Would you rather give each other space or always stick together?
20. Would you rather celebrate big wins or appreciate small moments?
21. Would you rather have adventurous dates or relaxing ones?
22. Would you rather grow together or stay the same?
23. Would you rather support my dreams or have me support yours?
24. Would you rather talk through every problem or leave some things unsaid?
25. Would you rather be best friends or passionate lovers?

Hard Would You Rather Questions

1. Would you rather lose your phone or your wallet?
2. Would you rather give up coffee or chocolate forever?
3. Would you rather have no friends or no family?
4. Would you rather win $1 million today or $10 million in 10 years?
5. Would you rather always feel too hot or too cold?
6. Would you rather have one true friend or 10 acquaintances?
7. Would you rather spend a year in jail or five years without me?
8. Would you rather lose all your money or all your possessions?
9. Would you rather always lie or always hear the truth?
10. Would you rather fail at something you love or succeed at something you hate?
11. Would you rather give up your favorite hobby or your favorite food?
12. Would you rather live without music or movies?
13. Would you rather never be able to travel or never be able to settle down?
14. Would you rather spend your life working or your life alone?
15. Would you rather lose your sight or your hearing?
16. Would you rather always be 10 years older or 10 years younger?
17. Would you rather live in the same place forever or move every year?
18. Would you rather never be able to celebrate holidays or birthdays?
19. Would you rather be rich and unhappy or poor and happy?
20. Would you rather always have to tell the truth or never speak again?
21. Would you rather lose your sense of taste or sense of smell?
22. Would you rather have no sleep for 48 hours or no food for 24 hours?
23. Would you rather have no phone for a week or no internet for a day?
24. Would you rather always be alone or always be surrounded by people?
25. Would you rather forget the best moment of your life or relive the worst one?

Thought-Provoking Would You Rather Questions

1. Would you rather be able to stop time or speed it up?
2. Would you rather know the meaning of life or why humans dream?
3. Would you rather live as someone else for a day or live as yourself forever?
4. Would you rather discover alien life or find life after death?
5. Would you rather be feared or respected?
6. Would you rather know everyone’s deepest secret or share yours with the world?
7. Would you rather eliminate hate or eliminate ignorance?
8. Would you rather live in a society with no rules or too many rules?
9. Would you rather invent something groundbreaking or discover something ancient?
10. Would you rather have the ability to solve one global problem or five personal problems?
11. Would you rather be able to travel through time or parallel universes?
12. Would you rather be remembered for your kindness or your intellect?
13. Would you rather lose your sense of identity or your ability to connect with others?
14. Would you rather explore the mysteries of space or the human brain?
15. Would you rather choose your destiny or let fate decide?
16. Would you rather live without pain or without joy?
17. Would you rather help one person achieve their dream or achieve yours at their expense?
18. Would you rather be completely honest or live a life of small lies?
19. Would you rather question everything or accept everything?
20. Would you rather live in a world without crime or without disease?
21. Would you rather have endless creativity or endless wisdom?
22. Would you rather know what happens after death or never die?
23. Would you rather witness the beginning of time or the end of time?
24. Would you rather always wonder “what if” or never ask the question at all?
25. Would you rather live in an eternal cycle of reincarnation or in a permanent afterlife?

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Final Thoughts

Relationships thrive on small, meaningful interactions, and this is such an easy, lighthearted way to create more of those moments. 

Whether you’re using them to break the ice, liven up a date night, or just pass the time on a lazy Sunday, these questions give you a chance to laugh, learn, and grow closer. Plus, let’s be honest, some of the answers might surprise you in the best way.