300 Cute & Flirty Would You Rather Questions (Plus a Generator)

Looking to impress your crush, partner, or date? Well, why not break the ice with a flirtatious game of Would You Rather? This classic party game can be played in person or over the phone, making it perfect for just about any occasion. If you’re not sure what flirty questions to ask, no worries! We interviewed professional dating coaches to compile a list of the cutest, silliest, deepest, and spiciest Would You Rather questions for your romantic interest. And if you want to keep the flirty times rolling, try our Would You Rather generator to create some totally new and fun questions for your crush or partner!

Flirty “Would You Rather” Questions to Ask a Girl or Guy

Would you rather be the big spoon or the little spoon?
Would you rather receive a sexy message or a love note?
Would you rather kiss in the rain or under the stars?
Would you rather have your kisses taste like candy or your favorite cocktail?
Would you rather whisper sweet nothings or receive them?

Section 1 of 8:

Flirty Would You Rather Questions

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Ask your crush some fun, flirty questions. Playing a flirty game of “Would You Rather” is a great way to let your crush know you’re interested. Depending on the questions you ask, you can also find out whether you’re romantically compatible. Here are some ideas:
- Would you rather be kissed all day or teased all day?
- Would you rather kiss me here… or here?
- Would you rather be the big spoon or the little spoon?
- Would you rather date someone younger than you or older than you?
- Would you rather receive a sexy message or a love note?
- Would you rather receive cheek kisses or forehead kisses?
- Would you rather get a sensual shoulder rub or a foot rub from your partner?
- Would you rather show affection in public or in private?
- Would you rather send a flirty text message or receive one from your crush?
- Would you rather share a passionate kiss or a secret you’ve never told?
- Would you rather flirt with your eyes or through playful, teasing banter?
- Would you rather whisper sweet nothings or receive them?
- Would you rather give a flirty wink or blow a cheeky kiss across the room?
- Would you rather kiss in the rain or under the stars?
- Would you rather exchange spontaneous kisses or indulge in a long, passionate embrace?
- Would you rather cuddle for an hour or kiss for 10 minutes straight
- Would you rather go on a romantic weekend getaway or have a cozy night together?
- Would you rather dance under the stars or share a midnight picnic?
- Would you rather go skinny dipping or do a boudoir shoot?
- Would you rather have someone use a dirty pickup line on you or use one on someone else?
- Would you rather watch a steamy movie or listen to a seductive song?
- Would you rather have a partner who loves to dance seductively or one who enjoys cooking romantic meals?
- Would you rather never be able to see your crush or never hear their voice?
- Would you rather have your kisses taste like candy or your favorite cocktail?
- Would you rather hook up with your celebrity crush or your high school crush?
- Would you rather never be able to touch or talk to your crush?
- Would you rather flirt with someone using a pick up line or just with body language?
- Would you rather kiss everyone you meet or never be able to kiss anyone again?
- Would you rather switch clothes with your partner or be naked all weekend?
- Would you rather make out in the rain or on the top of a Ferris wheel?
- Would you rather write a love letter to someone or share your feelings on video?
- Would you rather spend a cold day under the covers with your crush or by the fireplace?
- Would you rather wear socks or a hat during every hookup you have for the rest of your life?
- Would you rather play naughty Charades or have a sexy scavenger hunt?
- Would you rather be woken up with a kiss or with breakfast in bed?
- Would you rather never live out your wildest fantasy or never get married?
- Would you rather try pole dancing or lap dancing?
- Would you rather be allergic to hooking up or allergic to love?
- Would you rather have a partner who loves to tease or is more straightforward?
- Would you rather go on a blind date or date someone long-distance?
Meet the wikiHow Experts

Julianne Cantarella is a dating coach and the CEO and president of New Jersey’s Matchmaker. She has over a decade of experience.

Damona Hoffman is a dating coach, on-air personality, and best-selling author. She has over 15 years of experience and has consulted for numerous dating apps like OkCupid, Match, and Bumble.

John Keegan is a dating coach and motivational speaker based in NYC. He has over 15 years of experience and runs The Awakened Lifestyle, where he uses his expertise in dating to help people find love.

Section 2 of 8:

Cute Would You Rather Questions

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Keep things fun and lighthearted. Not all flirty questions have to be sensual. Woo your crush by asking cute, romantic questions instead! Or, simply get to know them better by asking fun, lighthearted questions. Here are some examples:
- Would you rather be kissed in the rain or in the dark?
- Would you rather have dessert before or after a meal?
- Would you rather hold hands or hug?
- Would you rather kiss me or not?
- Would you rather date your best friend or a stranger?
- Would you rather wake up with the sun or watch the moon rise?
- Would you rather be snowed in or stranded on a beach?
- Would you rather sleep under the stars or stay in a nice hotel?
- Would you rather be kissed on the cheek or lips?
- Would you rather tell someone how you feel over the phone or in person?
- Would you rather find love today or win the lottery?
- Would you rather receive a sentimental or expensive gift?
- Would you rather watch a romantic comedy or read a romance book?
- Would you rather take a long walk on the beach or go for a hike?
- Would you rather have cake or pie for your birthday?^{[1]
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- Would you rather go on a date to a water park or a theme park?
- Would you rather skip Halloween or Christmas?
- Would you rather give up your favorite food or your favorite TV show?
- Would you rather only eat ice cream or pizza for the rest of your life?
- Would you rather be good at playing every musical instrument or good at singing?
- Would you rather be able to speak every language or talk to animals?
- Would you rather play a game of Never Have I Ever or Truth or Dare?
- Would you rather have your art hung in a museum or have your portrait hung in a gallery?
- Would you rather only own cats or dogs?
- Would you rather visit every city on earth or travel to space?
- Would you rather have the perfect first date or the perfect wedding day?
- Would you rather only watch Pixar movies or only watch Disney movies?
- Would you rather go on a game show or a reality show?
- Would you rather it always be summer or always be winter?
- Would you rather have every meal you eat for the rest of your life be a little too spicy or a little too sweet?
- Would you rather not eat your favorite meal ever again or have to eat only that meal forever?
- Would you rather stay in a fancy hotel room or in a cozy cabin in the woods?
- Would you rather know what your pets think of you or never hear them speak?
- Would you rather live in a world where it constantly snows or always rains?
- Would you rather live in a world without music or a world without movies?

Section 3 of 8:

Silly Would You Rather Questions

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Use humor to break the ice. If you want to get a little flirty with your crush, dating and relationship coach Julianne Cantarella recommends using humor.^{[2]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview} Asking some fun, silly questions can help ensure your crush feels comfortable around you before you dive into more flirty questions. Here are some examples:
- Would you rather sing karaoke or do the Macarena?
- Would you rather live in a musical or a music video?
- Would you rather eat potatoes or cheese for the rest of your life?
- Would you rather date a superhero or a spy?
- Would you rather have a mohawk or mullet haircut?
- Would you rather have a private plane or be able to teleport?
- Would you rather be on a dating show or a survival show?
- Would you rather have an unlimited gift card to McDonald’s or Wendy’s?
- Would you rather tell your dirtiest secrets to your boss or parents?
- Would you rather have hands for feet or feet for hands?
- Would you rather only be able to walk backwards or skip?
- Would you rather only speak in rhyme or sing everything?
- Would you rather have a lion or an elephant as a pet?^{[3]
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- Would you rather have super strength or super speed?
- Would you rather be reincarnated as a dog or cat?
- Would you rather date someone with bad breath or BO?
- Would you rather lose your Netflix subscription or your Spotify premium?
- Would you rather have an Irish accent or an English accent?
- Would you rather delete Instagram or TikTok?
- Would you rather be covered in hair or have no hair at all?
- Would you rather have no baths for a month or no internet for a month?
- Would you rather have the hiccups for the rest of your life or always feel like you have to sneeze?
- Would you rather only be able to whisper or only be able to shout?
- Would you rather eat cold pizza or hot cereal?
- Would you rather not be able to control your laughter or not be able to control your tears?
- Would you rather have the BFG’s ears or Pinocchio’s nose?
- Would you rather fight 100 chicken-sized cows or one cow-sized chicken?
- Would you rather have a photographic memory or the memory of a goldfish?
- Would you rather fall on stage at your graduation or forget your speech?
- Would you rather have a head the size of a watermelon or a golf ball?
- Would you rather have to communicate in only emojis for a day or speak in rhyme for a week?
- Would you rather have a personal theme song that plays when you walk into a room or your own laugh track that follows your jokes?
- Would you rather have a never-ending sneeze or an uncontrollable urge to dance whenever you hear music?
- Would you rather have to talk like a pirate for a day or speak in a Shakespearean accent for a week?
- Would you rather be able to turn invisible but only when no one is looking or have the ability to teleport but only to places you’ve never been before?
- Would you rather have to communicate solely through interpretive dance for a day or speak only in puns for a week?
- Would you rather have a magic remote control that can pause or rewind real-life moments or a magic microwave that can instantly heat any food?
- Would you rather have the ability to change the color of your hair at will or the power to make inanimate objects come to life and chat with you?
- Would you rather have everyone you know be able to read your thoughts or everyone you know have access to your internet history?
- Would you rather only have weird dreams or never be able to dream again?

Section 4 of 8:

Deep Would You Rather Questions

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Learn what truly matters to your crush. Asking flirty “would you rather” questions is fun and all, but sometimes, you want to get to know your crush or partner on a deeper level. Try asking some of these deep questions to learn about their goals and motivations:
- Would you rather have your dream partner or dream job?
- Would you rather have your friends’ or parents’ approval?
- Would you rather get married now or never get married?
- Would you rather have kids or travel the world?
- Would you rather date someone you trust but don’t love or someone you don’t trust but love?
- Would you rather be friends with an ex or never talk to them again?
- Would you rather be loved or be in love?
- Would you rather predict the future or change the past?
- Would you rather go back in time to meet your grandparents or go to the future to meet your grandchildren?
- Would you rather have more money or more friends?^{[4]
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- Would you rather have money to burn or time to kill?
- Would you rather experience the world beginning or the world ending?
- Would you rather be homeless or in prison?
- Would you rather lose your sight or your memories?
- Would you rather have no sex forever or no meaningful conversations forever?
- Would you prefer to be the only one laughing at someone or the only one being laughed at?
- Would you rather be loved or respected?
- Would you rather be the last person on earth or the first person on earth?
- Would you rather win a million dollars or earn a million dollars?
- Would you prefer to be remembered as successful or as kind?
- Would you rather have a successful career but limited time for family or a less successful career with more time for family?
- Would you rather always know the truth, no matter how painful, or live in blissful ignorance?
- Would you rather spend your life constantly exploring new places or build a deep sense of belonging in one location?
- Would you rather know the exact moment of your own death or the moment of your partner’s death?
- Would you rather have the power to end world hunger or bring an end to all wars?
- Would you rather know the ultimate purpose of your life or have the freedom to create your own purpose?
- Would you rather have the strength to forgive any wrongdoing or the power to seek justice for all wrongs?
- Would you rather know the date of your death or the cause of your death?
- Would you rather get rich in a way that upsets your daily or make just enough money to live?
- Would you rather never age mentally or never age physically?
- Would you rather live one 1000-year life or ten 100-year lives?
- Would you rather fulfill your biggest wish or resolve your biggest regret?
- Would you rather marry the person of your dreams or have the career of your dreams?
- Would you rather feel like you know your partner better than anyone or feel like they make you happier every day?
- Would you rather lose all of the money you earned this year or lose all of the memories you made this year?

Section 5 of 8:

Spicy Would You Rather Questions

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Spice things up with some dirty questions. Make sure your partner or crush is okay with answering more risqué questions so you don’t make them feel uncomfortable. Asking spicy questions is a great way to learn what they like in the bedroom. Who knows—it may even be a good form of foreplay! Here are some examples:
- Would you rather make out in the back seat of a car or in a dark closet?
- Would you rather go skinny dip in the ocean or a lake?
- Would you rather do it with your socks on or off?
- Would you rather get a striptease or give a striptease?
- Would you rather use ice cream or whipped cream in the bedroom?
- Would you rather kiss your ex or enemy?
- Would you rather have a one-night stand with Harry Styles or Taylor Swift?
- Would you rather kiss every person in the room or sleep with one person in the room?
- Would you rather give up kissing or give up sex?
- Would you rather go on a date or just make out?^{[5]
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- Would you rather have a sexy shower or a sexy bath?
- Would you rather be constantly surprised in bed or always know what’s coming?
- Would you rather send a nude or receive one?
- Would you rather have sex in the morning or at night?
- Would you rather cheat and be caught or be cheated on and never be told?
- Would you rather have 10 years with your partner or a one-night stand with your celebrity crush?
- Would you rather hook up in the car or in the shower?
- Would you rather I show you or tell you about my desires?
- Would you rather have more roleplay or more foreplay?
- Would you rather have a sex playlist with classical music on it or hardcore rock?
- Would you rather have a cupboard full of sex toys or sexy outfits?
- Would you rather be focused on being romantic or being dirty?
- Would you rather go skinny dipping or join the Mile High Club?
- Would you rather keep your relationship closed and monogamous or be open to exploring other people?
- Would you rather share your spicy search history or read your partner’s?
- Would you rather always have vanilla sex or explore BDSM?
- Would you rather share your wildest fantasy or reveal your most embarrassing intimate moment?
- Would you rather accidentally send a sexy text to your boss or your parents?
- Would you rather skinny dip at midnight or sunbathe nude?
- Would you rather be a bad kisser or be bad at sex?
- Would you rather use whipped cream or chocolate sauce for foreplay?
- Would you rather swap partners with one of your friends or hook up with a stranger?
- Would you rather watch a steamy movie or read a steamy book with your partner?
- Would you rather have a partner who is great at talking dirty or one who is great at physical affection?
- Would you rather get a risqué package at work or a risqué photo during a meeting?
- Would you rather only be able to see people naked or be able to hear people’s dirty thoughts?
- Would you rather your soulmate have a weird kink or only call you by an annoying pet name?
- Would you rather accidentally flash a neighbor or a parent?
- Would you rather have a friend with benefits or a one-night stand?
- Would you rather be teased with a feather or ice cubes?

Section 6 of 8:

Would You Rather Questions for Your Crush

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Learn about your crush’s interests with these questions. Playing “Would You Rather” is a great way to get to know your crush better… and figure out if they like you. Keep things casual with some non-flirty questions, or use some romantic questions to hint about your feelings. Here are some examples:
- Would you rather get a box of chocolates or a bouquet of roses?
- Would you rather be told about the location of a date or surprised?
- Would you rather receive a good morning or a good night text?
- Would you rather have a private chef or a driver to take you anywhere?
- Would you rather make the first move or wait for someone else to?
- Would you rather marry the world’s smartest or hottest person?
- Would you rather have a shy or outgoing partner?
- Would you rather be with someone who’s always late or always early?
- Would you rather live in an RV or a mansion?
- Would you rather see me every day or never see me at all?
- Would you rather go a year without watching movies or listening to music?
- Would you rather eat funnel cake at a fair or popcorn at the movies?
- Would you rather have to go on 100 first dates or spend the rest of your life with your next date?
- Would you rather go on a road trip or go backpacking?
- Would you rather be Batman or Superman?
- Would you rather kiss a stranger or marry your friend?
- Would you rather date someone you met online or someone your friend introduced you to?
- Would you rather know the exact moment you’ll meet your soulmate but never have any other romantic relationships or have many romantic relationships but never know if you’ve met your soulmate?
- Would you rather have your heart broken or break someone else’s heart?
- Would you rather go on a date without being able to see or without being able to talk?
- Would you rather have your crush only speak in riddles or only speak in rhyme?
- Would you rather have your crush serenade you with a love song in public or make you something special in the kitchen in private?
- Would you rather kiss someone who always wears a lot of lip gloss or who always has chapped lips?
- Would you rather have your mom or your dad set up and run your dating apps?
- Would you rather be confronted by all the people you’ve ever rejected or be confronted by all the people who’ve ever rejected you?
- Would you rather go on a spontaneous getaway or plan an elaborate romantic date?
- Would you rather have your crush hear you talking about them or accidentally post their name as your FB status?
- Would you rather have the perfect body or be with someone who has a perfect body?
- Would you rather be on The Bachelor or Love is Blind?
- Would you rather date someone similar to you or the complete opposite?
- Would you rather have a late-night or an early-morning date?
- Would you rather date someone who is athletic or creative?
- Would you rather accidentally kiss a coworker or a friend?
- Would you rather have a partner who enjoys playful banter or who is more serious and romantic?
- Would you rather fall in love with a vampire or a zombie?

Section 7 of 8:

Would You Rather Questions for a First Date

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Ask “would you rather” questions to get to know your date better. Celebrity dating coach Damona Hoffman likes asking questions that are low stakes, but that everyone has an opinion on.^{[6]
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Expert Source

Damona Hoffman
Celebrity Dating Coach

Expert Interview} Not only is this a fun way to break the ice and start a conversation, but throwing in a few questions that are a bit more serious can help you determine if you and your date are compatible. Here are some examples:
- Would you rather date someone you like more or someone who likes you more?
- Would you rather live in the city or the country?
- Would you rather spend the day at home or out and about?
- Would you rather watch a romantic comedy or a horror movie?
- Would you rather star in a reality show or a game show?
- Would you rather pay for a meal or have someone pay for you?
- Would you rather find true love or be a millionaire?
- Would you rather have a lot of pets or children?
- Would you rather say “I love you” to everyone or never say it again?
- Would you rather have all your photos or Google search history be made public?
- Would you rather always be late or early?
- Would you rather be too hot or too cold?
- Would you rather live in New York or LA?
- Would you rather only eat fast food or healthy food forever?
- Would you rather be known for being attractive or being funny?
- Would you rather listen to the same song forever or only be able to watch the same movie forever?
- Would you rather always be underdressed or always be overdressed?
- Would you rather be a famous artist or a famous athlete?
- Would you rather be the only one drunk at a party or the only one sober?
- Would you rather be your partner’s first love or their last?
- Would you rather have ten close friends or one best friend?
- Would you rather be the smartest person in the room or the funniest?
- Would you rather have a partner who is always honest but critical or one who tells white lies to spare your feelings?
- Would you rather stay in or go out on a Friday night?
- Would you rather be a leader or a follower?
- Would you rather date an introvert or an extrovert?
- Would you rather have birthday presents or birthday experiences?
- Would you rather always get up at 5 a.m. or never go to bed before midnight?
- Would you rather not know what you look like or not know what you sound like?
- Would you rather be with the same person for most of your life or with many different people?
- Would you rather be 30 minutes early to every appointment or 30 minutes late?
- Would you rather have a partner with a possibly life-threatening job or a totally time-consuming job?
- Would you rather have six kids or not be able to have any?
- Would you rather be really personally fulfilled or really professionally fulfilled?
- Would you rather commit a minor crime on a first date or get matching tattoos on the first date?

Section 8 of 8:

Would You Rather Questions for Your Partner

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Keep your partner on their toes with some fun “would you rather” questions. Dating coach John Keegan says “Would You Rather” is a fun game to play with your partner.^{[7]
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Expert Source

John Keegan
Dating Coach

Expert Interview} Try to think of some unique questions you haven’t asked them before. This can help you learn new things about them, even if you know them really well! These questions work well for new relationships and couples who have been together for years:
- Would you rather never hug me again or never kiss me again?
- Would you rather see a movie every week or go on a wild adventure?^{[8]
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- Would you rather only be able to text or call me ever again?
- Would you rather ask for help or do things on your own?
- Would you rather get up early or sleep in late?
- Would you rather have more time or more money?
- Would you rather live in a big city or a small town?^{[9]
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- Would you rather wear my underwear or go commando?
- Would you rather be constantly surprised or always know what’s coming?
- Would you rather elope or have a big wedding?
- Would you rather get stuck in an elevator with your ex and their partner, or with your partner and their ex?
- Would you rather celebrate lots of little relationship milestones or just one big one every year?
- Would you rather only have female children or only have male children?
- Would you rather have kids before marriage or after marriage?
- Would you rather have the power to change one event in your partner’s past to make their life better or change one event in your own past to benefit your relationship?
- Would you rather we met in our teens or when we did?
- Would you rather we do date night once a week or one week of date nights a month?
- Would you rather know everything about my past or everything about my future?
- Would you rather face life’s challenges together or always have an easy life but apart?
- Would you rather have a surprise date planned for you or plan a surprise date for me?
- Would you rather get embarrassed in front of your in-laws or in front of your partner’s boss?
- Would you rather all your friends dislike your partner or your partner dislike your friends?
- Would you rather explore a new city together or spend a weekend in a luxurious hotel?
- Would you rather give a hickey or get a hickey?
- Would you rather sleep in the nude or in something sexy?
- Would you rather have a partner who spits when they talk or who chews loudly?
- Would you rather your friends or your parents arrange a marriage for you?
- Would you rather be wooed with poetry or with song?
- Would you rather have an intimate date with aphrodisiac foods or a passionate wine tasting evening?
- Would you rather read dating books or go to couples therapy?
- Would you rather slow dance or grind with someone you love?
- Would you rather find a love letter in a glass bottle at the beach or one hidden in your favorite book?
- Would you rather never be able to hold hands or never be able to cuddle?
- Would you rather give the perfect gift or receive it?
- Would you rather know everything that’s happening in your partner’s mind or nothing at all?
- Would you rather be serenaded by your partner or your favorite musician?
- Would you rather go on a romantic and relaxing vacation or a non-stop adventure?
- Would you rather spend your free time with a loved one or alone?
- Would you rather receive flowers or chocolate?
- Would you rather have someone make you your favorite meal or go out to a new restaurant?

Would You Rather Generator

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