650 Would You Rather Questions for Your Boyfriend

Ready to get to know your boyfriend even better? “Would you rather” questions are a super fun way to dive into his thoughts and feelings.

Whether you’re laughing over silly choices or getting serious about future plans, these questions make conversation easy and exciting! So go ahead, start asking, and see where the journey takes you both.

About Love and Romance

1. Would you rather have a fancy dinner date or a cozy night in?
2. Would you rather write me a love letter or sing me a love song?
3. Would you rather hold hands or hug?
4. Would you rather surprise me with gifts or spend quality time with me?
5. Would you rather be romantic or practical?
6. Would you rather say “I love you” first or wait for me to say it?
7. Would you rather kiss in the rain or dance in the rain?
8. Would you rather go on a road trip or fly to a romantic destination?
9. Would you rather plan out our dates or be spontaneous?
10. Would you rather cook together or order takeout?
11. Would you rather celebrate anniversaries or not make a big deal about them?
12. Would you rather watch romantic movies or action movies with me?
13. Would you rather talk on the phone or text?
14. Would you rather have deep conversations or keep it light and fun?
15. Would you rather be my best friend or my lover?
16. Would you rather go out dancing or stay in and cuddle?
17. Would you rather be affectionate in public or keep it private?
18. Would you rather go on double dates or just the two of us?
19. Would you rather go to a fancy event or a casual hangout?
20. Would you rather make future plans or live in the moment?
21. Would you rather share everything with me or keep some things private?
22. Would you rather have a long-term relationship or keep things casual?
23. Would you rather meet my parents or have me meet yours first?
24. Would you rather say something that’s on your mind or keep it to yourself?
25. Would you rather be too busy or have too much free time together?
26. Would you rather be overly romantic or not romantic at all?
27. Would you rather get up early for a sunrise date or stay up late for a starry night?
28. Would you rather go on fun adventures or have chill days?
29. Would you rather take pictures together or enjoy the moment without photos?
30. Would you rather be the big spoon or the little spoon?
31. Would you rather have pet names for each other or call each other by your real names?
32. Would you rather listen to love songs or podcasts together?
33. Would you rather go on a beach vacation or a mountain getaway?
34. Would you rather celebrate Valentine’s Day or think it’s overrated?
35. Would you rather propose to me or have me propose to you?
36. Would you rather go to couples therapy or figure things out on our own?
37. Would you rather be with me 24/7 or have some time apart?
38. Would you rather watch the sunset or the sunrise together?
39. Would you rather go to a party as a couple or stay in for a movie night?
40. Would you rather be emotional or logical in a relationship?
41. Would you rather pick me up for a date or have me come to you?
42. Would you rather show love through actions or words?
43. Would you rather be super cheesy or super serious?
44. Would you rather give gifts or receive gifts?
45. Would you rather be lovey-dovey or more independent?
46. Would you rather get married soon or take your time?
47. Would you rather focus on careers first or focus on us?
48. Would you rather have kids early or wait a while?
49. Would you rather grow old together or stay young at heart?
50. Would you rather spend forever with me or keep wondering, “What if?“

About Future Plans

1. Would you rather live in a big city or a small town?
2. Would you rather save money for retirement or spend on experiences now?
3. Would you rather start a business together or work separate jobs?
4. Would you rather travel the world or stay close to home?
5. Would you rather buy a house soon or rent for a while?
6. Would you rather get a pet soon or wait a few years?
7. Would you rather have a big wedding or a small, intimate one?
8. Would you rather go back to school or learn on the job?
9. Would you rather take a gap year to travel or keep working?
10. Would you rather focus on work or go on a long vacation together?
11. Would you rather start a family soon or wait?
12. Would you rather have many friends or a few close ones?
13. Would you rather invest in stocks or real estate?
14. Would you rather live near family or move far away?
15. Would you rather be a stay-at-home parent or both work?
16. Would you rather drive a practical car or a fancy one?
17. Would you rather work a 9-5 job or have flexible hours?
18. Would you rather volunteer together or donate to causes?
19. Would you rather live minimalistically or have a lot of stuff?
20. Would you rather do DIY projects or hire professionals?
21. Would you rather go out every weekend or stay home?
22. Would you rather have early mornings or late nights?
23. Would you rather live somewhere with four seasons or just summer?
24. Would you rather eat out often or cook at home?
25. Would you rather go to the gym together or exercise at home?
26. Would you rather have a busy social calendar or keep it simple?
27. Would you rather have a big family or a small one?
28. Would you rather work for someone else or be your own boss?
29. Would you rather take short trips often or go on long vacations?
30. Would you rather have a planned life or go with the flow?
31. Would you rather have a garden or live in an apartment?
32. Would you rather go to concerts or enjoy quiet evenings?
33. Would you rather pursue hobbies separately or try new things together?
34. Would you rather live frugally or splurge occasionally?
35. Would you rather retire early or keep working?
36. Would you rather celebrate holidays extravagantly or keep it low-key?
37. Would you rather be famous or live a private life?
38. Would you rather own a boat or a vacation home?
39. Would you rather take risks or play it safe?
40. Would you rather host parties or be a guest?
41. Would you rather live debt-free or take loans for bigger plans?
42. Would you rather live in the same place forever or move around?
43. Would you rather do local trips or international adventures?
44. Would you rather learn a new language or a new skill?
45. Would you rather go on double dates often or keep it just us?
46. Would you rather join a club or have a hobby at home?
47. Would you rather focus on mental health or physical health?
48. Would you rather live in an old-fashioned home or a modern one?
49. Would you rather be a homeowner or a world traveler?
50. Would you rather plan everything or take each day as it comes?

About Your Relationship

1. Would you rather make decisions together or trust each other to decide?
2. Would you rather keep secrets or be an open book?
3. Would you rather be jealous or indifferent?
4. Would you rather solve fights with conversation or give each other space?
5. Would you rather be more alike or have differences to balance each other out?
6. Would you rather play it safe or take risks as a couple?
7. Would you rather share the same interests or have your own hobbies?
8. Would you rather be with someone who challenges you or someone who agrees with you?
9. Would you rather have a big argument or small misunderstandings?
10. Would you rather show love through acts of service or words of affirmation?
11. Would you rather know everything about me or still have surprises?
12. Would you rather have more mutual friends or separate friend groups?
13. Would you rather be the one to apologize first or wait for me to do it?
14. Would you rather compromise or find a new solution to problems?
15. Would you rather be financially stable but busy or have more time but less money?
16. Would you rather have many small celebrations or few big ones?
17. Would you rather be more protective or more trusting?
18. Would you rather have a long-distance relationship or be close but see each other less?
19. Would you rather be sentimental or not keep things for memory?
20. Would you rather share responsibilities or have specific roles?
21. Would you rather be more playful or serious in our relationship?
22. Would you rather face challenges head-on or avoid conflict?
23. Would you rather be a power couple or be low-key?
24. Would you rather be competitive or cooperative with each other?
25. Would you rather have weekly date nights or spontaneous outings?
26. Would you rather be sensitive or thick-skinned in our relationship?
27. Would you rather have traditional roles or modern ones?
28. Would you rather go to social events together or solo?
29. Would you rather have the same political views or different ones?
30. Would you rather give more freedom or set boundaries?
31. Would you rather go to bed angry or stay up resolving the issue?
32. Would you rather be equal partners or have one lead more often?
33. Would you rather laugh off mistakes or learn from them?
34. Would you rather share social media accounts or keep them separate?
35. Would you rather have inside jokes or shared stories?
36. Would you rather be really private or openly share about our relationship?
37. Would you rather handle stress together or give each other space?
38. Would you rather change for each other or stay as you are?
39. Would you rather share all your feelings or keep some to yourself?
40. Would you rather be more spontaneous or more predictable?
41. Would you rather be optimistic or realistic about our future?
42. Would you rather go to couple’s activities or enjoy alone time?
43. Would you rather be overly committed or a bit detached?
44. Would you rather give up something for the other or find a middle ground?
45. Would you rather be romantic on special occasions or just because?
46. Would you rather consult each other for every decision or be independent?
47. Would you rather be overly affectionate or a bit distant?
48. Would you rather be best friends first or lovers first?
49. Would you rather make sacrifices for each other or find a way for both to win?
50. Would you rather be known for how strong our love is or how long it lasts?

About Fun and Random Stuff

1. Would you rather go skydiving or bungee jumping?
2. Would you rather be able to fly or be invisible?
3. Would you rather eat only pizza for a year or never eat pizza again?
4. Would you rather be a superhero or a villain?
5. Would you rather spend a day at an amusement park or a day at the beach?
6. Would you rather be a famous musician or a famous actor?
7. Would you rather have a pet dinosaur or a pet dragon?
8. Would you rather be a wizard or a Jedi?
9. Would you rather time travel to the past or the future?
10. Would you rather fight one horse-sized duck or a hundred duck-sized horses?
11. Would you rather always wear sandals or never wear socks?
12. Would you rather win the lottery or live twice as long?
13. Would you rather eat only spicy food or only bland food?
14. Would you rather live in space or under the sea?
15. Would you rather always be 10 minutes late or 20 minutes early?
16. Would you rather be a famous athlete or a renowned scientist?
17. Would you rather never use social media again or never watch TV again?
18. Would you rather have the power to read minds or control time?
19. Would you rather be able to teleport or create clones of yourself?
20. Would you rather be able to speak every language or play every instrument?
21. Would you rather have a rewind button or a pause button for your life?
22. Would you rather have more time or more money?
23. Would you rather be incredibly talented but not recognized or mediocre but famous?
24. Would you rather go camping or stay in a luxury hotel?
25. Would you rather eat a worm or walk on hot coals?
26. Would you rather have a mullet or be bald?
27. Would you rather be a stand-up comedian or a talk show host?
28. Would you rather have your dream job or a dream vacation?
29. Would you rather be stuck in an elevator or lost in a forest?
30. Would you rather only be able to whisper or only be able to shout?
31. Would you rather always lose or never play?
32. Would you rather give up coffee or give up soda?
33. Would you rather have unlimited tacos for life or unlimited sushi for life?
34. Would you rather be famous but disliked or unknown but loved?
35. Would you rather never be able to eat meat or never be able to eat vegetables?
36. Would you rather be in a zombie apocalypse or an alien invasion?
37. Would you rather have a permanent clown makeup or permanent face tattoos?
38. Would you rather always have to sing or always have to dance?
39. Would you rather go to a rock concert or a classical music concert?
40. Would you rather be a night owl or an early bird?
41. Would you rather live without music or live without movies?
42. Would you rather be stuck on an island alone or with someone you dislike?
43. Would you rather have a tail or have horns?
44. Would you rather always be cold or always be hot?
45. Would you rather be a professional gamer or a professional YouTuber?
46. Would you rather always be overdressed or always be underdressed?
47. Would you rather have the ability to change the past or see into the future?
48. Would you rather go on a reality TV show or host a cooking show?
49. Would you rather eat dessert for every meal or never eat dessert again?
50. Would you rather never age mentally or never age physically?

About Travel

1. Would you rather go on a road trip or fly to our destination?
2. Would you rather travel to a tropical island or a snowy mountain?
3. Would you rather go backpacking across Europe or take an RV across America?
4. Would you rather explore new places or revisit favorites?
5. Would you rather stay in a luxury hotel or a cozy Airbnb?
6. Would you rather go on an adventurous safari or relax at an all-inclusive resort?
7. Would you rather go sightseeing all day or relax at the beach?
8. Would you rather visit historical places or natural wonders?
9. Would you rather take a cruise or a hot air balloon ride?
10. Would you rather have an endless travel budget but can only stay in one place for a week, or a limited budget but can stay as long as you want?
11. Would you rather hike up a mountain or scuba dive in the ocean?
12. Would you rather travel by train or by boat?
13. Would you rather take a cooking class in Italy or go wine tasting in France?
14. Would you rather visit a big city or a secluded countryside?
15. Would you rather travel during peak season or off-season?
16. Would you rather take spontaneous trips or plan everything in detail?
17. Would you rather go on a food tour or an art tour?
18. Would you rather have a city view or ocean view from your hotel room?
19. Would you rather take a lot of short weekend trips or one long vacation?
20. Would you rather experience the culture or enjoy the nature of a place?
21. Would you rather go on a solo trip or a group tour without each other?
22. Would you rather spend a day at a theme park or a national park?
23. Would you rather explore the desert or the rainforest?
24. Would you rather have to pack super light or take everything you want but have to carry it all?
25. Would you raher travel back in time to meet your ancestors or forward to meet your descendants?
26. Would you rather camp in the wilderness or glamp with amenities?
27. Would you rather visit the North Pole or the South Pole?
28. Would you rather go skiing in the Alps or surfing in Australia?
29. Would you rather take a cooking class abroad or a dance class?
30. Would you rather go to a festival in another country or a quiet retreat?
31. Would you rather travel with family or friends?
32. Would you rather be a tourist or a traveler?
33. Would you rather go sailing or kayaking?
34. Would you rather have an action-packed itinerary or just go with the flow?
35. Would you rather travel to space or the deepest part of the ocean?
36. Would you rather visit all the countries in the world or go to outer space?
37. Would you rather have a five-star dining experience or a picnic on the beach?
38. Would you rather go zip-lining in a jungle or paragliding over a city?
39. Would you rather take a gondola in Venice or a tuk-tuk in Thailand?
40. Would you rather take a long drive along the coast or through the mountains?
41. Would you rather visit every continent or every ocean?
42. Would you rather go to a popular destination or a hidden gem?
43. Would you rather take photos or write a journal during our travels?
44. Would you rather go on a pilgrimage or a spiritual retreat?
45. Would you rather travel for a year with no home base or be a digital nomad?
46. Would you rather have more layovers but cheaper tickets or direct flights but more expensive?
47. Would you rather explore one country deeply or visit many but briefly?
48. Would you rather travel during your birthday or during a holiday?
49. Would you rather have all your trips planned by a travel agency or do all the planning yourself?
50. Would you rather end a trip with a relaxing spa day or an exciting adventure?

About Movies and TV Shows

1. Would you rather watch a comedy or a thriller?
2. Would you rather binge-watch a new show or pace it out?
3. Would you rather watch a classic movie or the latest blockbuster?
4. Would you rather see a movie in the theater or at home?
5. Would you rather be in a drama series or a reality TV show?
6. Would you rather watch only one genre forever or watch every genre but your favorite?
7. Would you rather have a movie night at home or go to a drive-in theater?
8. Would you rather star in a horror movie or a romantic comedy?
9. Would you rather watch a TV show before it’s cool or after the hype has died down?
10. Would you rather have a walk-on role in your favorite show or have your life turned into a movie?
11. Would you rather only watch shows with short episodes or long episodes?
12. Would you rather rewatch your favorite series or never be able to watch it again?
13. Would you rather be a superhero or a super villain in a movie?
14. Would you rather watch movies with subtitles or dubbed in another language?
15. Would you rather skip the intro of a show every time or watch it every time?
16. Would you rather be a movie critic or a TV show reviewer?
17. Would you rather have the ability to act or direct movies?
18. Would you rather watch a mystery or a fantasy?
19. Would you rather always watch the bad ending first or never know how a movie ends?
20. Would you rather be stuck in a comedy movie or a drama movie?
21. Would you rather watch animated movies or live-action?
22. Would you rather be in a sitcom or a soap opera?
23. Would you rather watch only independent films or only mainstream movies?
24. Would you rather be part of a film festival jury or attend award shows?
25. Would you rather be an extra in a blockbuster or have a big part in a small indie film?
26. Would you rather watch everything in black and white or in exaggerated colors?
27. Would you rather be able to produce movies or write screenplays?
28. Would you rather meet your favorite actor or your favorite director?
29. Would you rather watch all movies alone or always have to watch in a group?
30. Would you rather have an endless supply of popcorn or never be able to eat during a movie?
31. Would you rather only watch trailers or only read reviews before seeing a movie?
32. Would you rather only watch adaptations or original stories?
33. Would you rather watch a movie series in order or out of order?
34. Would you rather always guess the plot twist or never see it coming?
35. Would you rather watch a movie based on a book or a video game?
36. Would you rather have a cozy movie day or go to a film marathon at a theater?
37. Would you rather watch only TV shows that got canceled or only shows that finished?
38. Would you rather only watch documentaries or musicals?
39. Would you rather only watch silent movies or movies without a soundtrack?
40. Would you rather voice an animated character or play a character in costume?
41. Would you rather only watch foreign films or only local films?
42. Would you rather be able to quote every movie or remember every plot?
43. Would you rather go to the premiere of a movie or the finale of a TV show?
44. Would you rather watch movies without any special effects or with too many special effects?
45. Would you rather only watch movies from the ’80s or from the 2000s?
46. Would you rather watch something that makes you laugh or something that makes you think?
47. Would you rather see the behind-the-scenes or just enjoy the final product?
48. Would you rather watch a spin-off or a sequel?
49. Would you rather only watch award-winning shows or shows that are popular but not critically acclaimed?
50. Would you rather live in a world based on your favorite movie or your favorite TV show?

About Food Preferences

1. Would you rather eat pizza or burgers for the rest of your life?
2. Would you rather give up chocolate or give up cheese?
3. Would you rather cook dinner at home or go out to eat?
4. Would you rather eat spicy food or sweet food?
5. Would you rather have pancakes or waffles for breakfast?
6. Would you rather eat only fruits or only veggies?
7. Would you rather go to a fancy restaurant or a food truck?
8. Would you rather have ice cream or cake?
9. Would you rather eat fried food or grilled food?
10. Would you rather give up coffee or give up tea?
11. Would you rather eat a big breakfast or a big dinner?
12. Would you rather have homemade meals or takeout?
13. Would you rather eat with chopsticks or with your hands?
14. Would you rather have a salty snack or a sweet treat?
15. Would you rather eat seafood or meat?
16. Would you rather go to a steakhouse or a sushi bar?
17. Would you rather drink soda or fruit juice?
18. Would you rather have soup or salad?
19. Would you rather eat the same meal every day or never eat the same meal twice?
20. Would you rather have beer or wine with dinner?
21. Would you rather eat pasta or rice?
22. Would you rather eat fresh food or comfort food?
23. Would you rather skip appetizers or desserts?
24. Would you rather have cookies or brownies?
25. Would you rather eat healthy but not tasty food or tasty but not healthy food?
26. Would you rather eat Mexican food or Italian food?
27. Would you rather go on a picnic or have a BBQ?
28. Would you rather eat bread or tortillas?
29. Would you rather have butter or margarine?
30. Would you rather eat cake with frosting or without frosting?
31. Would you rather eat meat well-done or medium-rare?
32. Would you rather eat indoors or outdoors?
33. Would you rather eat fast food or home-cooked meals?
34. Would you rather eat a hot dog or a sandwich?
35. Would you rather eat alone or with a group?
36. Would you rather drink smoothies or milkshakes?
37. Would you rather eat a donut or a muffin?
38. Would you rather eat without seasoning or with too much seasoning?
39. Would you rather eat vegan food or gluten-free food?
40. Would you rather eat French fries or onion rings?
41. Would you rather drink still water or sparkling water?
42. Would you rather eat dark chocolate or milk chocolate?
43. Would you rather eat hard candy or chewy candy?
44. Would you rather eat a big meal once a day or small meals throughout the day?
45. Would you rather have cereal or oatmeal for breakfast?
46. Would you rather eat farm-to-table or eat whatever is available?
47. Would you rather eat nuts or chips as a snack?
48. Would you rather eat fruit whole or in a fruit salad?
49. Would you rather have a cold drink or a hot drink?
50. Would you rather eat savory breakfasts or sweet breakfasts?

About Hobbies and Interests

1. Would you rather read books or listen to podcasts?
2. Would you rather play video games or board games?
3. Would you rather go hiking or fishing?
4. Would you rather play a team sport or an individual sport?
5. Would you rather take up painting or photography?
6. Would you rather learn to play the guitar or the piano?
7. Would you rather go to a live concert or a live sports game?
8. Would you rather write a blog or make YouTube videos?
9. Would you rather collect stamps or coins?
10. Would you rather go to a museum or an art gallery?
11. Would you rather do DIY projects or buy things ready-made?
12. Would you rather watch the news or read the newspaper?
13. Would you rather go to a comedy show or a magic show?
14. Would you rather join a book club or a fitness club?
15. Would you rather learn to cook or learn to bake?
16. Would you rather garden indoors or outdoors?
17. Would you rather learn a new language or a new instrument?
18. Would you rather do puzzles or crosswords?
19. Would you rather go camping or go to a spa for relaxation?
20. Would you rather do yoga or weightlifting?
21. Would you rather dance or sing?
22. Would you rather go to a theater play or a movie?
23. Would you rather listen to music or watch TV to unwind?
24. Would you rather do a solo hobby or one we can do together?
25. Would you rather build models or solve Rubik’s Cubes?
26. Would you rather go to an amusement park or a zoo?
27. Would you rather watch documentaries or reality shows?
28. Would you rather learn woodworking or pottery?
29. Would you rather take up knitting or sewing?
30. Would you rather go birdwatching or stargazing?
31. Would you rather go thrift shopping or to a flea market?
32. Would you rather play chess or checkers?
33. Would you rather watch cartoons or anime?
34. Would you rather explore new hobbies or master one?
35. Would you rather listen to audiobooks or read eBooks?
36. Would you rather play cards or dice games?
37. Would you rather have a game night or a movie night?
38. Would you rather have a small hobby that’s cheap or a big hobby that’s expensive?
39. Would you rather go for a run or a swim?
40. Would you rather be good at cooking or at mixology (making drinks)?
41. Would you rather learn calligraphy or drawing?
42. Would you rather explore caves or climb trees?
43. Would you rather collect physical photos or digital photos?
44. Would you rather be in a choir or a band?
45. Would you rather do extreme sports or water sports?
46. Would you rather visit libraries or bookstores?
47. Would you rather play traditional sports or e-sports?
48. Would you rather have a hobby that’s indoors or outdoors?
49. Would you rather join a social club or a fitness club?
50. Would you rather learn magic tricks or juggling?

About Family and Friends

1. Would you rather live close to your family or travel and live far away?
2. Would you rather have a big family gathering or a small one?
3. Would you rather spend holidays with family or with friends?
4. Would you rather have a lot of friends or just a few close ones?
5. Would you rather be the funny one or the wise one in your friend group?
6. Would you rather be close with your siblings or with your cousins?
7. Would you rather go on a trip with family or friends?
8. Would you rather introduce me to your family or your friends first?
9. Would you rather spend weekends with family or hang out with friends?
10. Would you rather have your friends be similar to you or completely different?
11. Would you rather have family dinners at home or at a restaurant?
12. Would you rather celebrate your birthday with family or with friends?
13. Would you rather be friends with your neighbors or keep to yourself?
14. Would you rather have your family visit us often or just on special occasions?
15. Would you rather go to family reunions or avoid them?
16. Would you rather have friends who are older or younger than you?
17. Would you rather have deep talks with family or with friends?
18. Would you rather be the one who gives advice or gets advice in your family?
19. Would you rather have family game nights or movie nights?
20. Would you rather have childhood friends or make new friends as an adult?
21. Would you rather live in the same place as your family or move around?
22. Would you rather have family traditions or create new ones with me?
23. Would you rather have a pet considered as family or just as a pet?
24. Would you rather spend Christmas with family or take a vacation with friends?
25. Would you rather be famous in your friend group or unknown but happy?
26. Would you rather work with family or keep work separate?
27. Would you rather have friends who are more outgoing or more introverted?
28. Would you rather make friends through hobbies or through work?
29. Would you rather be the planner or the attendee for family events?
30. Would you rather have serious or silly friends?
31. Would you rather be friends with your co-workers or keep it professional?
32. Would you rather have couple friends or keep our friendships separate?
33. Would you rather have a close relationship with your parents or a more distant one?
34. Would you rather have friends who live close by or are spread around the world?
35. Would you rather have friends come to our place or go to their place?
36. Would you rather help a family member move or a friend move?
37. Would you rather have your friends and family get along or keep them separate?
38. Would you rather have weekly calls with family or rare but long visits?
39. Would you rather make friends easily or take time to build strong bonds?
40. Would you rather be close with your extended family or just your immediate family?
41. Would you rather be the one to initiate plans with friends or have them initiate?
42. Would you rather have family outings in nature or in the city?
43. Would you rather be friends with someone who’s always busy or always free?
44. Would you rather celebrate anniversaries with family or just us two?
45. Would you rather live in a community close to friends or isolated but peaceful?
46. Would you rather have a friend who’s always late or always too early?
47. Would you rather have a friend who’s brutally honest or super supportive?
48. Would you rather spend New Year’s Eve with family or friends?
49. Would you rather be mentored by a family member or a friend?
50. Would you rather be better friends with your boss or your employees?

About His Childhood

1. Would you rather have grown up in a big city or a small town?
2. Would you rather have been the oldest sibling or the youngest sibling?
3. Would you rather have had a treehouse or a clubhouse as a kid?
4. Would you rather have played indoor games or outdoor games?
5. Would you rather have had a lot of pets or no pets?
6. Would you rather have gone to summer camp or stayed home during vacations?
7. Would you rather have had strict parents or laid-back parents?
8. Would you rather have had a lot of friends in school or a few close ones?
9. Would you rather have been good at sports or good at academics?
10. Would you rather have watched cartoons or live-action shows as a kid?
11. Would you rather have ridden a bike or a skateboard?
12. Would you rather have been in a school band or on a sports team?
13. Would you rather have gotten toys or books as presents?
14. Would you rather have eaten homemade lunch or school cafeteria food?
15. Would you rather have moved around a lot or stayed in one place?
16. Would you rather have had a big family or a small family?
17. Would you rather have had chores or no chores?
18. Would you rather have played video games or board games?
19. Would you rather have learned to swim or to ride a bike first?
20. Would you rather have had birthday parties at home or at fun places like arcades?
21. Would you rather have watched movies or read books?
22. Would you rather have taken family trips or stayed home for holidays?
23. Would you rather have a cool tree to climb or a pond to swim in near your house?
24. Would you rather have been a scout or in a different kind of club?
25. Would you rather have taken dance lessons or music lessons?
26. Would you rather have participated in school plays or avoided them?
27. Would you rather have had a sandbox or a trampoline in your yard?
28. Would you rather have had hand-me-down clothes or new clothes?
29. Would you rather have been outgoing or shy as a kid?
30. Would you rather have had a themed bedroom or a plain one?
31. Would you rather have gone to public school or private school?
32. Would you rather have learned cooking or fixing stuff as a kid?
33. Would you rather have been a helper in the kitchen or in the garden?
34. Would you rather have visited amusement parks or nature parks?
35. Would you rather have had holiday traditions or spontaneous celebrations?
36. Would you rather have taken art classes or sports classes?
37. Would you rather have gone fishing or hiking with family?
38. Would you rather have liked science or history in school?
39. Would you rather have been a class clown or a teacher’s pet?
40. Would you rather have built forts out of pillows or out of wood?
41. Would you rather have gone to sleepovers or had friends come over to your place?
42. Would you rather have collected action figures or sports cards?
43. Would you rather have been active in the morning or a night owl?
44. Would you rather have played with Legos or Play-Doh?
45. Would you rather have had a big playground or a big library nearby?
46. Would you rather watch TV after school or play outside?
47. Would you rather have liked snow days or sunny days more?
48. Would you rather have been into dinosaurs or into space?
49. Would you rather have taken family photos often or just on special occasions?
50. Would you rather have had a favorite toy or a favorite book?

About Life Milestones

1. Would you rather buy a house first or travel the world?
2. Would you rather get married young or wait until you’re older?
3. Would you rather have kids right away or spend time as a couple first?
4. Would you rather focus on your career or on our relationship?
5. Would you rather go back to school or start your own business?
6. Would you rather retire early or work as long as you can?
7. Would you rather save for the future or live in the moment?
8. Would you rather celebrate big anniversaries or every small milestone?
9. Would you rather have a big wedding or a small, intimate one?
10. Would you rather have a fancy car or a reliable, simple one?
11. Would you rather be a homeowner or live a more nomadic life?
12. Would you rather reach career success early or gradually over time?
13. Would you rather pay off debt fast or take it slow and steady?
14. Would you rather write a book or have a book written about you?
15. Would you rather climb the corporate ladder or be self-employed?
16. Would you rather have a single, lifelong career or multiple jobs in different fields?
17. Would you rather focus on work-life balance or go all in on your career?
18. Would you rather adopt a pet before or after having kids?
19. Would you rather buy our first home or invest in real estate?
20. Would you rather have a destination wedding or get married close to home?
21. Would you rather spend your 30th birthday quietly or with a big bash?
22. Would you rather become famous for something or remain low-key?
23. Would you rather go on a world tour or have a year-long staycation?
24. Would you rather get advanced degrees or have on-the-job learning?
25. Would you rather win the lottery or earn your wealth?
26. Would you rather have a traditional retirement or do something unconventional?
27. Would you rather be financially secure early or take risks while you’re young?
28. Would you rather have our parents live close by when we have kids or not?
29. Would you rather renew our vows often or just once at a special milestone?
30. Would you rather start a family tradition or continue one from your family?
31. Would you rather have a mid-life crisis or a smooth transition into each life stage?
32. Would you rather be an early bird or a night owl in your career?
33. Would you rather take frequent short vacations or infrequent long ones?
34. Would you rather be a trendsetter or follow tried-and-true paths in life?
35. Would you rather have a big social media following or keep your life private?
36. Would you rather be part of community events or stay out of the public eye?
37. Would you rather focus on mental milestones or physical ones, like running a marathon?
38. Would you rather have an elaborate proposal or a simple, intimate one?
39. Would you rather celebrate New Year’s by making resolutions or just go with the flow?
40. Would you rather get all our “firsts” over quickly or spread them out?
41. Would you rather have a steady, predictable life or one full of surprises?
42. Would you rather settle down in one place or have several homes around the world?
43. Would you rather pass down heirlooms or create new ones for our kids?
44. Would you rather have a 5-year plan or make decisions as we go?
45. Would you rather mark milestones with big parties or with meaningful rituals?
46. Would you rather be well-known in our local community or keep to ourselves?
47. Would you rather celebrate our achievements with gifts or experiences?
48. Would you rather be someone who listens to life advice or gives it?
49. Would you rather live by a set timeline for milestones or let them happen naturally?
50. Would you rather prioritize personal milestones or shared milestones as a couple?

About Philosophical Ideas

1. Would you rather have free will or a predetermined destiny?
2. Would you rather live in a world without pain or without pleasure?
3. Would you rather know all the truths in the universe or be blissfully ignorant?
4. Would you rather be eternally happy or have the full range of human emotions?
5. Would you rather live forever or have a short but meaningful life?
6. Would you rather be morally good but unhappy or morally questionable but happy?
7. Would you rather be super intelligent or super wise?
8. Would you rather live in an ideal virtual reality or an imperfect real world?
9. Would you rather always speak the truth or be able to tell white lies?
10. Would you rather be a big fish in a small pond or a small fish in a big pond?
11. Would you rather know when you’ll die or how you’ll die?
12. Would you rather have no sense of time or a perfect sense of time?
13. Would you rather have no fears or no regrets?
14. Would you rather be universally loved or universally respected?
15. Would you rather have all your thoughts broadcasted or never speak again?
16. Would you rather know all the secrets of space or all the secrets of the ocean?
17. Would you rather always know what’s right or always know what’s wrong?
18. Would you rather have one true love for a short time or many loves over a lifetime?
19. Would you rather be remembered forever or live in the moment?
20. Would you rather have world peace without freedom or freedom without world peace?
21. Would you rather be rich in a poor world or poor in a rich world?
22. Would you rather have fame and scrutiny or anonymity and obscurity?
23. Would you rather relive your best moment or redo your worst?
24. Would you rather be a leader in a troubled world or a follower in a peaceful world?
25. Would you rather be a skeptic or a believer?
26. Would you rather live in a world of justice or a world of mercy?
27. Would you rather be your best self for a day or your average self for a lifetime?
28. Would you rather be forgotten but make a big impact or be famous but make a small impact?
29. Would you rather be certain of something false or uncertain of something true?
30. Would you rather explore the mind or explore the world?
31. Would you rather have an ugly truth or a beautiful lie?
32. Would you rather be the first person to discover something or the last?
33. Would you rather be a hero in a tragedy or a villain in a comedy?
34. Would you rather be able to change the past or see into the future?
35. Would you rather live in a world of chaos or a world of order?
36. Would you rather always be busy or always have nothing to do?
37. Would you rather be completely logical or completely emotional?
38. Would you rather live with no history or no future?
39. Would you rather have a life of quality or a life of quantity?
40. Would you rather be in a constant state of evolution or reach a state of perfection?
41. Would you rather see the world in shades of gray or only in black and white?
42. Would you rather live a life full of passion or a life full of reason?
43. Would you rather be a creator or a destroyer?
44. Would you rather lose all your memories or never make new ones?
45. Would you rather be bound by honor or driven by ambition?
46. Would you rather be part of a collective consciousness or a unique individual?
47. Would you rather believe in an afterlife or in nothingness after death?
48. Would you rather be lost in the journey or fixated on the destination?
49. Would you rather live for the now or plan for the future?
50. Would you rather seek truth or seek meaning?

About Work and Career

1. Would you rather work from home or in an office?
2. Would you rather have a high-paying job you dislike or a low-paying job you love?
3. Would you rather be the boss or an employee?
4. Would you rather work in a team or work alone?
5. Would you rather have a stable 9-to-5 job or a job with flexible hours?
6. Would you rather have a short commute or a long commute with a better job?
7. Would you rather work on weekends and have weekdays off or the traditional Monday to Friday?
8. Would you rather have more vacation time or a higher salary?
9. Would you rather be an expert in one field or a jack-of-all-trades?
10. Would you rather work in a creative job or an analytical job?
11. Would you rather climb the corporate ladder or stay in a comfortable position?
12. Would you rather have lots of work friends or keep work and life separate?
13. Would you rather wear a suit to work or dress casually?
14. Would you rather have a long career in one company or switch jobs every few years?
15. Would you rather work in a big company or a small startup?
16. Would you rather have a job that involves travel or stay close to home?
17. Would you rather be self-employed or work for someone else?
18. Would you rather have job security or job variety?
19. Would you rather work in a fast-paced environment or a laid-back one?
20. Would you rather have a job that helps people or a job that pays well?
21. Would you rather be overworked and overpaid or underworked and underpaid?
22. Would you rather take work calls at home or never have to think about work after hours?
23. Would you rather have a boring job with great co-workers or an exciting job with difficult co-workers?
24. Would you rather have an easy job with little recognition or a challenging job with accolades?
25. Would you rather work indoors or outdoors?
26. Would you rather have multiple part-time jobs or one full-time job?
27. Would you rather work with cutting-edge technology or traditional methods?
28. Would you rather have a job that’s mentally demanding or physically demanding?
29. Would you rather have no promotions but job security or frequent promotions with risk?
30. Would you rather work with animals or with computers?
31. Would you rather be famous in your field or have a strong private life?
32. Would you rather do the same tasks every day or always be tackling something new?
33. Would you rather work for a socially responsible company or a profitable one?
34. Would you rather have a job that lets you socialize or one that focuses on tasks?
35. Would you rather have a long lunch break but work late or a short lunch and leave early?
36. Would you rather have an active job or a desk job?
37. Would you rather work in a noisy environment or a quiet one?
38. Would you rather have a high-stress job with downtime or a moderate job with no breaks?
39. Would you rather have an easy job where time drags or a hard job where time flies?
40. Would you rather have a daily routine or a job where every day is different?
41. Would you rather take retirement early but work hard or work longer but at a relaxed pace?
42. Would you rather work in your dream job but never retire or in a decent job with early retirement?
43. Would you rather have a side hustle or focus solely on your main job?
44. Would you rather work in a field you’re passionate about or a field where you have natural talent?
45. Would you rather work with older, experienced people or younger, innovative people?
46. Would you rather commute by car or public transportation?
47. Would you rather work somewhere with high expectations but high rewards or low expectations but less growth?
48. Would you rather have your own office or an open-concept workspace?
49. Would you rather be skilled in something outdated or mediocre in something cutting-edge?
50. Would you rather have a job that impacts a few lives deeply or impacts many lives superficially?

Frequently Asked Questions

Can we turn it into a game?

Absolutely! You can make a game night out of it. Each of you can write down some questions on pieces of paper and take turns drawing them from a bowl. You can even set some rules or rewards for extra fun.

Can “Would You Rather” questions help solve relationship issues?

While these questions are generally meant for fun or deep conversations, they aren’t a substitute for serious relationship advice. If you’re dealing with big issues, it’s better to have an open, honest discussion or seek professional advice.