63 Flirty Would You Rather Questions – Spark great conversations.
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Would you rather have a set of flirty would you rather questions on hand for that next conversation when you really need to communicate just how interested you are to a girl, or would you rather just try to wing it and see it go wrong all over again?
A lot of men underestimate how important it is to have the right questions to ask on hand when the conversation starts getting hot and heavy. Some guys just come up with questions to ask a girl on the spot, but there’s always the risk that will go wrong. It’s far better to have fun questions to ask already in mind, so you know when the time comes, you won’t freeze.
These questions can be any kind you like, but for our money, would you rather questions have to be among the most fun.
You want flirty would you rather questions that are perfect for every situation, whatever your relationship status with the great gal you’re chatting with. For those ideal questions that always hit the mark, take a look at this list, where we’ve set down all the best would you rather questions that always charm the ladies.
Here are the 8 best flirty would you rather questions:
1. Would you rather be snowed in with your crush or lay on the beach with your crush?
Get the answer now, plan your future vacation later.
2. Would you rather hit on someone much older than you or have someone much older hit on you?
For those older gentlemen flirting with the younger generation.
3. Would you rather find true love or be rich?
Ideal question for those rich charmers who can offer both.
4. Would you rather go watch a movie or go watch the sunset?
Get her romantic preferences upfront.
5. Would you rather kiss me in public or kiss me in private?
A great way to cut the chase.
6. Would you rather dress up for a night on the town or stay home in sweats?
Is she a party at home or party at the club kind of girl?
7. Would you rather let your spouse date your best friend or your arch enemy?
A funny question to find out who is open to swinging.
8. Would you rather eat the food prepared by your mom or your boyfriend?
What does she really think of your cooking?
Here are 7 flirty but also funny would you rather questions:
9. Would you rather be rich and ugly, or poor and good-looking?
Easy to follow this up by reminder her she’s already good-looking.
10. You’re on a desert island with a beautiful woman or man. Would you rather they are top-half fish? Or they are bottom-half fish?
The eternal sailor’s question…
11. Would you rather have really weird dreams every single night or never have dreams again?
Then you can get her to describe her weirdest dreams.
12. Wrestle in a pool of Jello or chocolate pudding?
Sexy and delicious…
13. Would you rather be with a jealous hardworking girlfriend or a lazy but trusting girlfriend?
Get to know now before things go any further!
14. Would you rather have a partner who’s shy or one who makes you feel shy?
A good way to make your shyness an asset.
15. Would you rather go jogging together or go to the gym together?
An ideal question shared over a plate of nachos.
There’s always a risk with flirty would you rather questions that you tread a little too deep into dirty implications. For some girls—and some guys—that’s a territory you want to avoid. If that’s the case, keep your would you rather questions clean with these options.
Here are 7 flirty but clean would you rather questions:
16. Would you rather go on a date to a fancy restaurant that’s quite expensive or a cheap restaurant that’s quite rowdy?
Good clean fun, but where would she like to have it?
17. Would you rather jog in the daytime together or take strolls at night?
Getting physical together, in a totally clean and healthy way.
18. Would you rather your lover be one who likes to dress comfortably or one who likes to dress fashionably?
Get her expectations now.
19. Would you rather be with someone who’s feared or someone who’s loved by all?
She may be clean, but she can still be Machiavellian.
20. Would you rather have a lover who’s obsessed with pets or one who doesn’t like pets?
Good to know now if you’re either a serious dog lover or dog hater.
21. Would you rather try on your partner’s clothes or have your partner try on your clothes?
This is a bit kinky but still stays just on the right side of clean.
22. Would you rather date someone with no emotions or date a compulsive liar?
No good options, but her answer will be enlightening.
Nervous about keeping the conversation flowing on that first date? Everyone’s advice will be to ask her questions to show you’re interested, but you don’t want the same bland questions she’d heard before, particularly from other guys! Use these first date questions to get a flirty would you rather conversation going she’s definitely never had before.
Here are 7 flirty would you rather first date questions:
23. Would you rather be in a bad relationship for the rest of your life or have no relationship for the rest of your life?
A rough question, but an honest answer tells you a lot about her.
24. Would you rather ask for help or figure it out yourself?
Is she independent or looking for a knight in shining armor?
25. Would you rather fall in love with someone who’s allergic to all of your favorite food, or someone who makes embarrassing dad jokes?
Hope for the dad jokes, because that’s probably you.
26. Would You Rather hold my hand or put your arm around my waist?
Advance the conversation into the physical right on the first date.
27. Would you rather your boyfriend keep short hair or long hair?
A good one if you can pull off long locks.
28. Would you rather follow your heart or your head while making important decisions about your love life?
Now you know which to convince to get the second date.
29. Would you rather send your partner a good morning or a good night text?
Whichever it is, send her one after the date at the right time.
What would be the point of flirty would you rather questions if you weren’t talking to a girl you really like? These aren’t just questions to pass the time. These are questions to ask a girl you like that tell her you like her and charm her into feeling the same way.
Here are 8 flirty would you rather questions to ask a girl you like:
30. Would you rather stay friends with your ex or never talk to them again?
She’ll tell you about her ex and invite you into her confidence.
31. Would you rather experience unrequited love or never know how it feels to be in love?
It’s the former, and now she’s thinking about it while talking to you.
32. Would you rather have one partner or several at once?
Find out if she’s your type of girl…whichever type that is.
33. Would you rather keep searching for true love and keep getting heartbroken or give up after the first heartbreak?
Is she a romantic or a fatalist?
34. Would you rather tell your guy the bitter truth or comfort him with lies?
What would she do if the going got tough with you?
35. Would you rather marry a doctor or an athlete?
Ideal question for a sprinter in med school.
36. Would you rather to chat with me all night long or prefer calling for a smaller duration?
Her options are limited to having another chat later.
37. Would you rather have many kids or just one?
Show her you’re already thinking long-term.
Being part of a couple can be great, but there are always moments when the conversation can run out. That’s why you always want to have questions to ask couples ready, particularly some flirty would you rather questions that keep your conversation interesting and spicy!
Here are 8 flirty would you rather questions for couples:
38. Would you rather date someone who’s highly ambitious about their career, or someone who cares more about passions outside of work?
If you’re trying to balance both, find out which she prioritizes.
39. Would you rather be with someone who wants to start a family in the very near future or someone who’d like to wait a few years to really figure things out?
This starts a conversation you really need to have if things are getting serious.
40. Do you want to be with someone who’s confrontational and places the problem right on the table or someone who approaches issues between you in a more careful, gentle way?
If there’s a problem in the relationship, now you know how to broach it.
41. Would you rather date someone who’s interested in a very active social life, with parties and events and activities every other night, or someone who’s more of a homebody, and prefers to stay in with you or hang out in smaller, quieter groups?
When organizing your social life with a new partner, you’ll want to know if you agree on this.
42. Would you rather go on a date with Bugs Bunny or Mickey Mouse?
Spend a night getting into the all important WB vs. Disney debate.
43. Would you rather know every secret your spouse has or are some secrets better left uncovered?
Secrets exist in couples, best to know how she deals with them.
44. Would you rather skip work for a romantic date or date for office work?
A question for those overly work-obsessed partners. It reminds them to pay more attention to you.
45. Would you rather go watch a movie or go watch the sunset?
Refresh the relationship with a romantic evening of her choosing.
There’s all kind of flirty would you rather questions out there, but sometimes, you want to stump her even as you flirt with her. These hard would you rather questions are tough to answer, and they let her know you want her real thoughts on these topics.
Here are 9 flirty but hard would you rather questions:
46. Would you rather watch a fireworks show or go watch a musical?
A tough one if she loves the magic of both.
47. Would you rather me cook you breakfast in bed or have a candlelit dinner?
It’s a tough choice, so let her off the hook and let her have both.
48. Would you rather draw pictures in the sand or look for pictures in the clouds?
How does she express her lingering childhood imagination?
49. Would you rather become someone else or just stay you?
Really get at the heart of how she feels about herself.
50. Would you rather be on a survival reality show or dating game show?
A funny way to make her choose her hell.
51. Would you rather choose tenderness or passion?
What does she prioritize in love?
52. Would you rather lie and say the food your partner cooked is yummy or secretly feed it to the dog under the table and say nothing?
Ask this after you’ve cooked her dinner for a smile and some honest criticism!
53. Would you rather go shopping alone or together?
A really tough question for many women.
54. Would you rather get married or date infinitely?
A tough question you may have to ask if the relationship is stretching on without evolving.
Just because you’re flirting doesn’t mean you can’t show what a deep, thoughtful dude you are at the same time. These deep would you rather questions tell her that you really like her and that you really like thinking about the serious topics in life.
Here are 9 flirty but deep would you rather questions:
55. Would you rather be with someone who overly sensitive or overly insensitive?
Both represent problems, but which is worse for the person who loves them?
56. Would you rather your parents hated your partner or your partner hated your parents?
What kind of familial division is worse? And which is more likely with her?
57. Would you rather date someone who has the same religious orientation as you or would you not mind at all?
How devout is she in her beliefs? And how open is she to different worldview?
58. If your SO has a terminal disease, would you rather you know but they don’t or they know but you don’t?
It’s an awful thought, either way, but a very interesting thought experiment.
59. If you were to die tomorrow, would you rather be with your SO or your family today?
Who really holds her heart?
60. Would you rather have your partner look through all your text and chats or your employer look through all your text and chats?
Who would be more upset and whose opinion matters more?
61. Would you rather be with someone who is afraid to lose you or someone you are not afraid to lose?
Find out how scared she is of commitment.
62. Would you rather live forever and watch your loved ones all die or live a short life and die before all of your loved ones?
No good answers, but very different priorities in those answers.
63. Would you rather be with someone who is overly optimistic or overly pessimistic?
And does that match with how she sees the world or run counter to it?
With so may flirty would you rather questions on offer, your problem now is narrowing down your choices. You can’t just read her these lists, so you’ve got to make some choices.
To help you pick the real winners for you and your girl, follow these 4 steps to get your flirting queries down before your next chat.
Here is how to pick the best flirty would you rather questions:
1. Who is she?
While you cull your flirty would you rather question list, think about who this girl is and what kind of questions would appeal to her.
2. What are you trying to say to her?
At the same time, remember that these questions are doing more than passing the time, they’re telling her how you feel and what kind of guy you are. Choose questions that tell her the right things about you.
3. Choose earnest, funny, or a combination
There’s a big split in these questions: earnest vs. funny. Decide where you fall along that divide—or if you fall in between—and choose your questions accordingly.
4. Always bring back ups
Trying to get a laugh and the first question falls flat? Always have another ready to try a few minutes later. With enough options ready, you’re sure to hit on the right question with a couple tries.
Downloadable List of Flirty Would You Rather Questions
Here is a downloadable list of Flirty Would You Rather Questions (right click the image and select Save Image As…):
More Awesome Fun Questions To Ask
Once you’v run through all our flirty would you rather questions, we’ve got plenty more great questions to ask in every conversation, whether you’re looking to be flirty or not. Be sure to take a look at these fun, awesome questions:
- Have fun figuring out who’s most likely to end up president or in prison…or both with these questions.
- Satisfy your curiosity to the extreme with never have I ever questions that you’ll never get tired of asking.
- Got a bit of time on your hands? Time enough for 21 questions? Fill it with these great 21 questions game questions.
Flirty would you rather questions can come in every kind of topic for every kind of guy talking to every kind of girl. The key point is these are all questions to ask when you want an interesting conversation that’s leading somewhere…interesting. These fun questions to ask will get her smiling and let her know just how much you think of her.
There’s no limit to the right questions to ask a girl in a flirty conversations, so by all means add your own or your own spin to these lists, but when you need some would you rather questions that really show what you’d rather be doing, these do the job every time.