150 Flirty Would You Rather Questions To Ask

150 Flirty Would You Rather Questions To Ask A Guy

150 Flirty would you rather questions to ask a guy you like, your crush or your boyfriend. It’s the best and ONLY list that you’ll ever need!

“Would you rather have a fun, flirty conversation with your special someone or one that’s dull and boring?”. It doesn’t matter how old you are. It’s a fact that playing the “Would You Rather Game” is an excellent way to liven up any conversation.

It’s easy too! You can play with a guy or girl you like, your crush, partner, or as a couple with your boyfriend or girlfriend. With its notoriously flirty appeal exchanging “would you rathers” will definitely keep things interesting. Besides being great conversation starter. It’s also a good way to keep witty banter going while never running out of things to talk about. 

While yes, these questions are mostly designed to be asked in the spirit of flirtatious fun and aren’t meant to be taken too seriously. You can also keep in mind that in many ways they can tell you a lot about your partner. By way of giving you some very interesting insight into their likes and dislikes, and their hopes and dreams.

In turn, you may also learn a few things about your relationship or it’s potential too. Like whether or not you have things in common and how compatible you are as a couple.

To get things started we’ve compiled a list of the best “Would You Rather” flirty questions below. We’ve also included ones that are funny, silly, deep, romantic, a bit “dirty” and even some that are great for a first date. Let’s get started!

Flirty Would You Rather Questions For Him 

Use this list of fun and flirtatious questions to strike up an exciting game of “would you rather” with a guy you like. Your boyfriend or that guy you’re already dating.

  1. Would you rather kiss in the dark or kiss in the rain?
  2. Would you rather make the first move on a date or let your date make the first move?
  3. Would rather have endless money or endless love?
  4. Would you rather be your crush’s first love or their last?
  5. Would you rather sleep alone or with someone next to you?
  6. Would you rather kiss me or not?
  7. Would you rather give a gift or receive a gift?
  8. Would you rather love and lose, or never love at all?
  9. Would you rather end a date with a kiss or with a little bit of tension and mystery?
  10. Would you rather date someone who is good in the kitchen or good in bed?
  11. Would you rather be twice as smart as you are right now or twice as attractive?
  12. Rather be with a lover who is obsessed with pets or one who doesn’t like pets at all?
  13. Would you rather still be friends with an ex or never talk to them again?
  14. Would you rather take a vow of celibacy or take a vow of silence?
  15. Would you rather date someone who’s more attracted to a person’s looks or their brains?
  16. Would you rather be told where you are going on a date or have it be a surprise?
  17. Would you rather your mom or your ex set up and run your dating apps?
  18. Would you rather love your partner more or have them love you more? 

Flirty First Date Would You Rather Questions

First dates can be nerve racking. One way to by pass those first date nerves is to have a list of fun questions on hand. Which you can ask anytime to get the conversation started. Break out if you’re not sure what to talk about. Or really, anytime that you feel like you’re running out of things to say.

Use the questions below to break the ice with your date, while also getting to know them better. Who knows? You may even spark not just a flirty conversation but chemistry as well!

  1. Would you rather live in an apartment in the city or in a house in the countryside?
  2. Would you rather kiss on the first date or wait a few dates?
  3. Would you rather date a cat person or a dog person?
  4. Would you rather plan a holiday month in advance or get a flight last minute?
  5. Would you rather forget your date’s name one hour into a dinner date, or accidentally call them by your mom or dad’s name?
  6. Would you rather be the funniest person in the room or the best looking person in the room?
  7. Would you rather be in a bad relationship for the rest of your life or having no relationships at all for the rest of your life?
  8. Would you rather find out someone you really like HATES dogs, or find out they cheated on their ex?
  9. Would you rather find your true love in life or land your dream job?
  10. Would you rather star in a romantic comedy or a horror movie? 
  11. Would you rather always be late or always be early? 
  12. Would you rather meet someone on a dating app or at a bar?
  13. Would you rather hit the town for a night out of dinner and dancing or stay home with a bottle of wine?
  14. Would you rather run into your date’s most recent ex on a first date, or go on a date with someone who refuses to answer any questions about their ex?

More Cute And Flirty First Date Would You Rather Game Questions

Here are a few more playful questions for a first date. These are also great for any time during that early “getting to know you” stage. So feel free to bust them out on a second date or third date. As well as, anytime you feel like you’d want to jump start your conversation in a fun and interesting way.

  1. Would you rather go a year without netflix or a year without music?
  2. Would you rather pay for a meal or have someone pay for you?
  3. Would you rather send your partner a good morning text or a good night text? 
  4. Would you rather spend $5,000 on traveling or on a material item like a fancy TV?
  5. Would you rather be with a partner with a personality that’s really similar to you or someone completely different?
  6. Would you rather make important decisions about your love life by following your heart or your head?
  7. Would you rather on a first date run into your most recent ex, or run into both of your parents?
  8. Would you rather date someone who ONLY texts you or date someone who ONLY FaceTimes you?
  1. Would you rather have your partner look through all of your text, chat and email history or your boss?
  2. Would you rather casually date for a long time or fall in love quickly and get into a relationship as soon as possible?
  3. Would you rather go on a date with someone who can’t eat anything before they’ve posted it on Instagram, or go on a date with someone who live Tweets the entire date?
  4. Would you rather spend all day at home or all day out of the house?
  5. Would you rather go on a date with someone who’s really into high fives (even to strangers), or go on a date with someone who’s physically incapable of walking by a dog without stopping to pet it?
  6. Would you rather date someone who liked you more or someone who you liked more?
  7. Would you rather realize an hour into a first date that you’ve been out with this person before, or accidentally call them by your ex’s name three times in a row? 

Best Would You Rathers For Your Crush

Essentially, you can start a game of “Would You Rather?” to get to know your crush just a little bit better. While at the same time showing them that you’re fun, interesting and have a good sense of humor. Use this list flirty would you rather questions to ask your crush and soon you’ll find out if there’s any chance that there could be something more there.

  1. Would you rather make the first move or wait for a girl to do it?
  2. Would you rather be snowed in with your crush or stranded on a beach with your crush?
  3. Would you rather become good friends with your celebrity crush or go on one date with them?
  4. Would you rather get your text left on read or accidentally text a screenshot of your conversation to the person you’re talking to?
  5. Would you rather go on Love Island or Love Is Blind?
  6. Would you rather marry the hottest or smartest person alive?
  1. Would you rather let your partner date your best friend or your arch enemy?
  2. Would you rather be good looking but wind up with an ugly partner or be ugly and marry a extremely attractive partner?
  3. Would you rather be in a monogamous relationship or an open one? 
  4. Would you rather date someone you hardly know or someone that you consider a friend?
  5. Would you rather go on a date with a fictional tv show character or a book character?
  6. Would you rather have a partner who shy or one that makes you feel shy?
  7. Would you rather have universal respect or unlimited power?

More Flirty Questions For The Would You Rather Game

Though it may seem silly, you can never underestimate the power of a flirtatious game of “Would you rather”. It’s not just a simple way to break the ice with someone you like. If you ask the right questions. Well it may take your relationship in a interesting and exciting direction that you never saw coming.

  1. Would you rather find true love or be rich? 
  2. Would you rather be rich and unattractive or poor and good-looking?
  3. Would you rather marry your high-school sweetheart or your college hookup?
  4. Would you rather be on a reality show like survivor or the bachelor?
  5. Would you rather take amazing selfies but look terrible in all other photos or be photogenic everywhere but in your selfies?
  6. Would you rather date a wilderness lover or a city dweller?
  7. Would you rather have a really weird dreams every night or never have dreams again?
  8. Would you rather date someone who is great in bed but a lousy kisser or someone who is terrible in bed but a great kisser?
  9. Would you rather give a striptease or get a striptease?
  10. Would you rather suck someone’s earlobe or suck someone’s toes? 
  11. Would you rather date someone who is loved by your friends or loved by your family?
  12. Would you rather date someone who is well-dressed, well-read, well-connected, or well-traveled?
best flirty would you rather game questions for couples

Best Would You Rather Questions For Couples

Just because you’ve been a couple for sometime, doesn’t mean that should stop getting to know each other in new and interesting ways. The would you rather game was designed to be played with a partner. So adding flirty questions into the mix is the perfect opportunity switch things up. Get out of a rut and bring a little something different to your normal day to day relationship routine.

Break out these would you rather questions for couples the next time you’re on date night with your boo, on a road trip, or relaxing at home. Or really any time that you want to bring a little playfulness to your conversation! Enjoy!

  1. Would you rather choose to never have me hug you again or never kiss you again?
  2. Would you rather kiss me in public or kiss me in private?
  3. Would you rather give or receive?
  4. Would you rather ask for help or figure it out yourself?
  5. Would you rather tell me about your intimate fantasies or have me tell you about my juicy fantasies?
  6. Would you rather receive presents or experiences for your birthday?
  7. Would you rather kiss me all day or tease me all day?
  8. Would you rather go on a movie date or an adventure date?
  9. Would you rather never be able to hold hands again, or never be able to spoon again? 
  10. Would you rather have a great sex life but not get along well, or get along great but rarely have sex?
  11. Would you rather have sex only in bed or only in places that are more adventurous? 
  12. Would you rather have no sex forever or no emotional conversations forever?

For more ways to get a conversation going with your man. Check out our article here >>All about how to get a guy to open up and talk about his feelings.

best romantic would you rather questions couples boyfriend

Romantic Would You Rather Questions

Enjoy these would you rather romantic questions as a couple with your partner, or your boyfriend.

  1. Would you rather remember all your dreams or never remember your dreams? 
  2. Would you rather sleep in a tent under the stars or stay in a 5 star hotel?
  3. Would you rather get flowers from your partner or send them flowers?
  4. Would you rather kiss in public or kiss in private?
  5. Would you rather cuddle outside under the stars with a bottle of wine or cuddle under a blanket near a fireplace with hot chocolate?
  6. Would you rather sing to me or play me a song on a guitar?
  7. Would you rather take a shower with me or a candlelight bath with me? 
  8. Would you rather smell a rose or watch a sunset?
  9. Would you rather skinny dip in a lake or the ocean? 
  10. Would you rather receive a love letter or receive a poem? 
flirty adult would you rather questions

Spicy Adult Would You Rather Questions

Sometimes your relationship and life in the bedroom can get a bit dull and boring. This is where a “dirty” game of “Would You Rather” can come in handy. Ask the questions below with your partner to spice things up!

  1. Would you rather make love for hours but only once a week or have short, 5-minute sessions every day? 
  2. Would you rather be in a relationship with a totally submissive partner or a totally dominant partner?
  3. Would you rather give or receive a lap dance?
  4. Would you rather blindfold me or have me blindfold you?
  5. Would you rather make out with someone else or watch me make out with someone else?
  6. Would you rather join the mile-high club or have a threesome?
  7. Would you rather see me dressed up as a sexy librarian or a sexy cop?
  8. Would you rather be single forever or date someone with no interest in being physically Intimate?
  9. Would you rather lick or suck?
  10. Would you rather try hot wax play or blindfold play?
  11. Would you rather have your belly kissed or have your thighs kissed?
  12. Would you rather give one presentation at work naked or never see your partner naked again?
  13. Would you rather write erotica or make an erotic movie?
  14. Would you rather eat sushi or ice cream off someone’s body?
 deep would you rather questions for your boyfriend

Deep Would You Rather Questions 

These deep would you rather questions are designed to take your conversations well to just that – a deeper level.

  1. Would you rather be able to change the past or be able to predict the future?
  2. Would you rather date someone who is honest or someone who is compassionate?
  3. Would you rather be with someone that always tells the truth or someone that lies and protects your feelings?
  4. Would you rather never be able to cry or never be able to laugh?
  5. Would you rather experience unrequited love several times in a row or never know how it feels to be in love at all?
  6. Would you rather tell your partner a lie for a good reason or tell them the truth for a bad reason?
  7. Would you rather date someone who is highly ambitious and focused on their career or someone who cares more about their hobbies and passions outside of work?
  8. Would you rather be with someone who is overly positive or overly pessimistic?
The best list of deep would you rather questions for your boyfriend
  1. Would you rather be with someone who wants to start a family in the near future or someone who wants to wait a few years to figure things out?
  2. Would you rather be with someone who is afraid to lose you or someone you are not afraid to lose?
  3. Would you rather have your heart broken or be the heartbreaker?
  4. Would you rather know every secret your partner has or are there some secrets best left undiscovered?
  5. Would you rather have more time or more money?
  6. Would you rather be with someone who’s feared by all or someone who’s loved by all?
  7. Would you rather date someone who is highly extraverted and social and loves to go out to parties and events every other night or someone who is more of a homebody and likes to stay in as a couple or hang out in smaller quieter groups?
  8. Would you rather never use social media sites/apps again or never watch another movie or TV show?
  9. Would you rather go to a 10-hour-long concert of a band you hate or sit at a 10-hour-long dinner with a politician you hate?
  10. Would you rather your parents hated your partner or that your partner hated your parents?
  11. Would you rather be able to travel back in time if you could change history or would you rather travel to the future but not be able to change anything? 
  12. Would you rather give bad advice or get bad advice?
  13. Would you rather lose all of your money and valuables or all of the photos you have ever taken?
Laugh with your partner with these funny, flirty this or that would you rather questions.

Funny Would You Rather Questions

Funny but also flirty good would you rather questions to ask a guy you like or your boyfriend.

  1. Would you rather reveal your Instagram search history or make your DMs public?
  2. Would you rather fall in love with someone who’s allergic to all of your favorite foods, or fall in love with someone who makes embarrassing dad jokes every time you eat?
  3. Would you rather talk like a pirate or have a parrot on your shoulder at all times?
  4. Would you rather date someone who smelled like tobacco or ranch dressing all the time?
  5. Someone is about to take over the world – would you rather it be aliens or robots?
  6. Would you rather accidentally call your partner by your ex’s name, or have them do that to you?
  7. Would you rather kiss a smelly person or someone with bad breath?
Have more fun with your boyfriend with these funny, flirty this or that would you rather questions.

Silly Would You Rather Questions

These are good, random questions to ask when you want to up the fun factor of your conversation.

  1. Would you rather only Netflix or only chill for the rest of your life?
  2. Would you rather have Joe Exotic’s haircut from “Tiger King” or Edna Mode’s haircut from “The Incredibles”?
  3. Would you rather always have chapped lips or always have a stuffy nose?
  4. Would you rather only wear Crocs for the rest of your life or only watch Katherine Heigl movies for the next six months?
  5. Would you rather snort every time you laugh on a first date or kiss someone with coffee breath?
  6. Would you rather be able to talk to animals or be able to speak any language?
  7. Would you rather give up social media forever or be allergic to caffeine?
  8. Would you rather on every first date, have hiccups the whole time, or pass wind midway through and your date notices it and says something?
  9. Would you rather go on a long AF road trip with your ex or your enemy?
  10. Would you rather go on a date with someone who does magic tricks the entire time, or go on a date with someone who tries to sell you “As Seen On TV” knives at the end of the date?
  11. Would you rather kiss someone who always wears lots of sticky lip gloss or someone who always has dry, chapped lips?
  12. Would you rather only be able to speak in rhyme for an entire first date (without offering explanation), or have to recite the Pledge of Allegiance before each bite?
  13. Would you rather be stranded on a desert island with your ex or with your boss?
  14. Would you rather find your parents’ sex tape or have your parents find yours?

About Would You Rather Questions

The “Would Rather Questions” game, is also sometimes known as “This or That” or “What Would You Do”. To play the game you need two or more people and a set of questions that present two options. The choices are usually both equally appealing, unappealing or impossible to choose. Which are designed to make the questions entertaining and challenging to answer.

How To Play The Would You Rather Game

Playing a game of “Would You Rather” couldn’t be easier. The rules are as simple and straight forward as 1, 2, 3! You can play face to face, over text, on a date, a road trip or just relaxing at home.

1. First, decide on the list of questions that you want to ask. You can pick a theme, like flirty, funny, deep, get to know you, or impossible to choose. If you are already a couple and want to spice things up you can also ask questions that are more of a “dirty” version.

2. Next, take turns asking would you rather questions to each other. To get to know your partner better you can also talk about why they chose the answer that they did.

3. Finally, have fun flirting and getting to know one another better!

The Best Flirty “Would You Rather” Questions

The best flirty would you rather questions will help you discover new things about the other person. They may even reveal new surprising things about your partner that help develop your relationship and bring you closer.

Enjoy & Happy Flirting!

**THE NEXT STEP**

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