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20+ Playful & Flirty Would You Rather Questions for Guys

20+ Playful & Flirty Would You Rather Questions for Guys

Everyone knows how to play “would you rather”, but did you know that it’s a perfect excuse to be flirty with a guy you like The hard part about this game is thinking of would you rather questions for guys that are flirty and playful, and will capture his attention. Sound tricky? Don’t worry we’ve got you covered.

Here are 20+ would you rather questions for guys that are sure to pique his interest:


Would you rather questions for guys who you aren’t sure about

If you aren’t completely sure that this guy likes you, you’ll want to be more cautious with your questions.
Have a look at these would you rather questions for guys who you are unsure about.

01“Would you rather date someone who you already know or a complete stranger?”
This will help you find out if he is open to the idea of dating a friend or if he is against it. His answer will tell you whether you should continue flirting or give up on him altogether.


dinner date wine glass
Photo by Davids Kokainis on unsplash


02“Would you rather admit your feelings to a friend or keep it bottled up?”
When you suspect he might like you, but you aren’t entirely sure, a well-phrased question can help you can find out if he is just too shy to admit it.


03“Would you rather date a girl with beauty or brains?”
His response will reveal what kind of girl he’s into. You have nothing to worry about if you have both!


04“Would you prefer to date a girl who is younger than you or older than you?”
With a question like this, you can figure out if you stand a chance or not.


short haired girl photo coffee

Photo by Kinga Cichewicz on unsplash


05“Would you rather have a friend with benefits or an actual relationship?”
His answer will let you know if he‘s ready for a committed relationship or if he’s just looking to have fun.


06“Would you date a hot chick with an awful personality or an average looking girl with an amazing personality?”
The answer to this question will give you a sneak peek at what he values. It will let you know if appearances are more important to him than having a quality relationship.



07“Would you rather date a dominant or submissive woman?”
This question can carry a few different meanings, so it’s good to ask when you’re getting mixed signals. The answer to this will let you know what role he thinks a woman should play in a potential relationship.


beautiful girl sitting on the table
Photo by Brooke Cagle on unsplash


08“If you had to choose, would you rather date a girl who has had plastic surgery on her face or on her breasts?”
This is a good question because it will let you find out if he cares about those kinds of things, and, more importantly, if looks are more important to him than a woman’s personality.


09“For a date, would you rather dine out at a restaurant or cook at home?”
Asking this question will let you know if he is outgoing or not when it comes to relationships. It will also let you know if he considers himself a decent cook!


husband and wife cooking happily

Photo by Le Creuset on unsplash


10“If you had to choose one, would you rather have a full-blown PDA relationship or one with no affection?”
Not everyone is into PDA, but some people prefer an ultra-affectionate partner. When you ask this question, you will find out if he is the handsy type and will declare to the world that you guys are together, or if he will keep it a secret.


11“Would you rather have true love or infinite wealth?”
Love is an amazing thing, but so is having all the money you could ever want. By asking this question, you will find out if he values material things over love.



Would you rather questions for guys who you know are interested in you

If you already know he likes you, there’s no reason for you to be shy. Be bold and confident.
Here are 12 would you rather questions for a guy who already likes you.

12“Would you rather kiss me or hug me?”
This question lets you know how intimate he wants to be with you with no pretenses.


couple man and woman kiss
Photo by henri meilhac on unsplash


13“Would you rather see your girl in lingerie or her birthday suit?”
This question will help you prepare for your first sexual encounter. This way, you can make the experience great for him and you.


14“Would you rather kiss a girl who wears a lot of makeup or a girl who wears none.”
Asking this question will give you some insight into his preferences. Some guys like makeup, others hate it, and the rest don’t care. You’ll learn a little more about his priorities.


woman beauty face lipstick

Photo by Candice Picard on unsplash


15“Would you rather have planned sex in a bedroom, or spontaneous sex in a restaurant bathroom?”
This question is a little bit bold, but if you’re sure he likes you and you’re interested in a physical relationship, then go for it. This will give him a big hint about where your mind is at.


16“Would you rather have 12 kids or none at the all?”
This question is a bit far-fetched, but after all, it is would you rather. If he’s interested in having kids, then he will react to the first option. If he’s not into kids at all, you’ll find out.



17“Would you rather elope or have a big wedding?”
A question like this tells you about his values. Either option he chooses will give him a chance to explain his views. You’ll get some insight into the way his mind works.


newly wed couple kiss vehicle
Photo by Eliza Szablinska on unsplash


18“Would you rather see me naked or have both of us naked?”
This is another bold question, but it might be worth the ask. If he is brave enough to answer, the first option will show that he’s interested in the idea of seeing you naked.
The second option shows that he would prefer to be with you for the main event. Either way is a win.


19“Would you rather tell your girlfriend the truth or comfort her with lies?”
This is a deep and revealing question, but it’ simple enough to start an easy conversation. His answer will let you know what to expect during your relationship, and how much he values honesty.


20“Would you rather cuddle or make out?”
The difference between the two is subtle but distinct. With cuddling, you can talk and share an intimate moment without it being sexual, while making out, on the other hand, is fully sexual.
His answer to this will let you know what his intentions are.


photo kiss couple silhouette

Photo by Alejandra Quiroz on unsplash


21“Would you rather cheat with a stranger or with your ex?”
This is a very important question that you should pay close attention to. This will let you know if he still has feelings for his ex, and his answer can save you heartache in the long run.


22“Would you rather have a long, steamy session of lovemaking once a week, or a quickie every day?”
This question will let you know if he is the romantic type or if he just wants to do it and get it over with.



When you use these flirty would you rather questions for guys, you will be sending the right message, i.e., that you are interested. However, be careful with which questions you choose in case he isn’t as interested in you as you’d like him to be.