­85 Flirty Would You Rather Questions That'll Make An Impression

Flirty, funny and ridiculous 'Would You Rather' questions to play with

By Kat W
­85 Flirty Would You Rather Questions That'll Make An Impression

The Only Game You Should Play

“Would You Rather” is a fun, flirty, and easy game that allows you to know your new girl or guy, and it helps break the ice when you may not know what to say. The rules are simple: Ask a question that starts with "Would You Rather" and ends with two options. The person answering the question must choose from one of the two options. You should always try to be honest and answer the question with the choice that first pops into your head. But remember, there is no right or wrong answer! Some may add alternative rules, such as allowing a pass on a question, but only with consequences. 

man in brown drawstring pullover hoodie sitting on brown bench beside woman

Popular consequences of passing on a question are taking a shot (if you're of drinking age), eating/drinking something gross, completing a dare, or other silly and daring things. For a more erotic and flirty version of "Would You Rather," make anyone who passes on a turn take off one piece of clothing. You never know what it might lead too. No matter how you decide to play, "Would You Rather" can help you learn a surprising amount of information about someone just by asking a question. It gives you the chance to learn about the other person's preferences, desires, and even secret fantasies. Whether you ask funny, flirty, personal, or sexual questions, you are sure to come away knowing something you didn't before!

woman wearing black shirt

For Those Awkward First Dates

We've all been there. You're on the first date, and the conversation goes cold. You've asked all the generic first date questions, like "what's your favorite food, color, movie, etc.", so now what do you do? Learn about your date in a fun and exciting way! Playing "Would You Rather" gives you the chance to get to know the other person on a new level. Ask personal, funny, downright ridiculous, or even flirty questions, if you're feeling it. No matter what, you can't go wrong by starting with a few icebreakers!

man and woman making a toast

1. Would you rather live without pizza or sex for a year? Living without either of these would be a terrible fate!

2. Would you rather be stuck in an elevator with a bull or IT the clown?

3. Would you rather listen to rap music or country music? The type of music one listens to can tell you so much about them.

4. Would you rather build a snowman or a sand castle? Winter Wonderland or fun in the sun? Either way, you can’t go wrong!

5. Would you rather watch the sunset or sunrise?

6. Would you rather be rich and ugly or good looking and poor? Sadly, we all can't be wealthy and good looking.

7. Would you rather cook a meal together or have a meal cooked for you? Looks will fade, but cooking skills will last a lifetime!

8. Would you rather have true love or a million dollars?

9. Would you rather be snowed in with your crush or lay on the beach with your crush?

10. Would you rather build a house or buy a sports car with lottery winnings? You could always live in the small backseat of your car! 

man and woman holding hands

11. Would you rather sing in the car with me or sing karaoke to me? Singing skills not included.

12. Would you rather take a vow of celibacy or a vow of silence? Caution: This question may be difficult for those who love to talk.

13. Would you rather spend money on traveling or on material possessions?

14. Would you rather go skinny dipping or jump in fully clothed? If the option for no clothes is there, then let's get to stripping!

15. Would you rather be single or in a relationship? This could be an immediate game-changer! Learning the one you're pining after isn't looking for a relationship can destroy any ounce of courage you've worked up for telling them how you really feel.

Flirty Questions For Escaping The Friend Zone

four person looking at the city

Being friend-zoned stinks, but having a crush that is totally oblivious to how you feel is even worse! Sometimes you just want to shake them and yell "I LIKE YOU" in their face, but even then they still may not see it. Before you go crazy racking your brain with ways to veer out of the friend-zone or get your crush to notice you, play a little "Would You Rather" game! Just be careful and try not to get your hopes up, because the answers to your questions may not be what you are looking for. But hey, you never know what it could lead too.

16. Would you rather date someone you hardly know or someone who you consider a friend?

17. Would you rather a friend tell you they have feelings for you or keep it to themselves?

18. Would you rather friend-zone someone you know likes you or be honest with them? Honesty is the best policy.

19. Would you rather kiss me or not? Asking this flirty question could be a risky move, but it could be worth it.

20. Would you rather date me or just be my friend? This question is blunt and straight to the point!

Spice Up Your Date Night

flat screen TV

In a world of "Netflix and Chill," it can be daunting planning an original, well-thought-out date. You can only go to dinner and the movies so many times, right? It's essential to learn some personal preferences, likes and dislikes about your significant other so that you can plan your next perfect or adventurous date! What better way to do so than asking a series of "Would You Rather" questions about types of dates and adventures!

21. Would you rather stay at home and watch movies or go on an adventure?

22. Would you rather order take-out or go to a fancy restaurant? At least no one judges your eating habits at home.

23. Would you rather dance in the country under the stars or in the city under neon lights? Two-stepping or bumping and grinding, either way, you can't go wrong.

24. Would you rather go out for the night or stay in? Staying in for the night is cheaper, but we all deserve a fun night on the town.

25. Would you rather go on a double-date or go on a date alone? If you pick double-date, at least pick a couple you both like.

26. Would you rather go ice-skating or rollerblading? You can’t go wrong with either of these!

27. Would you rather go on a picnic or eat at a 5-star restaurant?

28. Would you rather go out for ice-cream or make our own sundaes at home? Ice cream at home is practically free.

29. Would you rather go to a sporting event or a concert?

30. Would you rather get dressed up for a night on the town or put on sweats for 'Netflix and Chill'? Sometimes sweats sound more appealing!

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Questions To Ask Your SO/Soon To Be SO

couple on bed using MacBook Air beside of window with white curtain

This next group of questions can help you discover what your potential or current significant other looks for in a partner. Try not to get too caught up in their answers to your questions, as they may not match exactly what you're like. Keep in mind you've made it this far, so they must like you for who you are!

31. Would you rather be friends with benefits or be in a relationship?

32. Would you rather kiss on the first date or wait you know her/him better? A kiss on the first date never hurt anyone.

33. Would you rather date someone who is funny or intelligent? Funny people tend to be more interesting!

34. Would you rather date someone who is honest or who is compassionate?

35. 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?

36. Would you rather date one person at a time or have multiple partners at once?

37. Would you rather wait a month for your significant other to return home from a trip to have sex or do it with a stranger now? We should all know the best answer to this one.

38. Would you rather date someone who is loved by your friends or loved by your family? Friends can change, but family is forever.

39. Would you rather have a one night stand or a long-term relationship?

40. Would you rather date someone who is well-dressed, well-read, well-connected, or well-traveled? Unfortunately, you can only pick one! 

man kissing woman on her forehead

41. Would you rather have a solely physical relationship or something more?

42. Would you rather cuddle or make out? Is both an option?

43. Would you rather sleep naked or in pajamas?

44. Would you rather sleep alone or with someone next to you?

45. Would you rather date someone who is good in the kitchen or good in bed? We can always order takeout.

46. Would you rather date someone who has the same hobbies as you or different hobbies than you? It's always fun to discover new things!

47. Would you rather hear "I love you" too often or not enough?

48. Would you rather propose/be proposed to in public surrounded by people or in private with just the two of you? A public proposal could get awkward..

49. Would you rather elope or have a big wedding?

50. Would you rather live in a skyrise condo or a house?

51. Would you rather have your own kids or adopt?

52. Would you rather live in a big city or a small town? Small town living isn’t so bad.

53. Would you rather have multiple kids or just one? The more the merrier, right?

Whether you're looking for a way to drop hints to your longtime partner or just looking to discover what your significant other see their future like, talking about the future can be scary and lead to awkward conversations. Make the conversation light-hearted by throwing in some "Would You Rather" questions!

Get Flirty With It.. In The Bedroom

man and woman lying on bed

No one wants to have that awkward conversation about what we do and don't like in the bedroom, but sometimes those conversations are necessary. Whether you're trying to spice things up in the bedroom or learn things your partner enjoys, get flirty with the dirty by asking a few "Would You Rather" questions that can make the conversation enjoyable, flirty, and a lot less awkward!

54. Would you rather make love in the shower or in the rain?

55. Would you rather join the mile high club or stick to the bed? Airplane bathrooms do not create the most romantic atmosphere.

56. Would you rather swim with sharks or go without making love for six months?

57. Would you rather try new positions in bed or stick to what you know? You should always keep things exciting in the bedroom! 58. Would you rather eat whipped cream off a sundae or me?

59. Would you rather spontaneously get it on in a dressing room or in a car? Public places can be an exciting risk.

60. Would you rather do foreplay or dive right in? There is nothing wrong with a little warm up.

61. Would you rather make love in the dark or with the lights on?

62. Would you rather be restrained to the bed or blindfolded during sex?

63. Would you rather kiss my lips or my body? As far as a flirty question goes, you can't go wrong with this one.

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Flirty Questions To Ask Her

woman lying on bed white holding board

Women are complicated; this is no secret. They often struggle answering questions that give them multiple options, such as where to eat, what nail color to do, or even what clothes to wear. While understanding them is almost impossible, they truly appreciate the effort you put forward to do so. While you may not learn her deepest darkest secrets or her heart's desire, you can learn if she prefers Chick-Fil-A over Chipotle.

64. Would you rather date a guy who can't grow facial hair or who always has a beard? #teambeard

65. Would you rather date a guy who is older or younger? As long as he’s mature, who cares!

66. Would you rather date a guy who lacks in brains but is extremely hot or an OK guy who is incredibly smart?

67. Would you rather make the first move or wait until he does? Some guys are slow to the plate! Sometimes a girl has to take the initiative.

68. Would you rather date a guy who is a bad boy or the self-proclaimed good guy?

69. Would you rather have an expensive material possession as a gift or an inexpensive sentimental item as a gift?

70. Would you rather date a guy with big muscles or a big package? 

71. Would you rather date a guy who wears boxers or briefs?

72. Would you rather date a guy who works hard but doesn't make a lot of money or a guy who doesn't work at all but is filthy rich? Hard-work makes the dream work.

73. Would you rather eat pizza and drink beer or eat lobster and drink wine?

74. Would you rather be loved by his sister or his mother?

Flirty Questions To Ask Him

man wearing blue crew-neck top and woman wearing orange spaghetti strap top standing seashore

Men are simple creatures who love sports, enjoy playing video games, and hate talking about their feelings, right? Wrong! While the above may be true for some men, not all are as easy to understand. Making an effort to learn little things about your man will go a long way with him, even if he doesn't show it. Get him to open up by asking a series of "Would You Rather" questions. If you're sneaky enough about it, he may not even realize what's going on!

75. Would you rather see your girlfriend with or without makeup? Be very careful answering this question!

76. Would you rather date a girl who dresses conservatively or who isn't afraid to show skin?

77. Would you rather date a girl who lacks in personality, but makes up for it in looks or a girl who lacks in looks, but makes up for it in her personality? Personality will always out live good looks.

78. Would you rather check a girl out from the front or the back?

79. Would you rather see your girl in lingerie or completely naked?

80. Would you rather make the first move or wait until she does? Always make the first move! Otherwise, she might think you’re uninterested.

81. Would you rather date a girl who is older or younger?

82. Would you rather date a girl with beauty or brains?

83. Would you rather date a girl who wears thongs or cheeksters?

84. Would you rather play video games or go to a sporting event? Find a girl who will do whatever you like with you.

85. Would you rather fall in love or have a one night stand? Love can last a lifetime, while one night lasts a few hours.

Final Word

man and woman cuddling on rooftop

“Would You Rather” questions are a great way to kickstart a conversation in a fun and interesting way. Ask ridiculously funny questions, get personal, be flirty, or stay simple. No matter what route you decide to take, this game can definitely have some interesting outcomes. While you can learn a lot about the other person when playing this game, try not to think too hard or read too much into their answers. This game is meant to be light-hearted and fun!

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