100 Most Uncommon Deep Would You Rather Questions

100 Most Uncommon Deep Would You Rather Questions

Would you rather questions are probably the optimized questions to enhance the crisp and fun level of a conversation. Whether you are chatting with your partner sitting miles away or you are having a discussion with your fellow who is sitting right in front of you, a deep and thoughtful “would you rather” question can ignite the flame of fun and curiosity to an ultimate level.

An uncommon would you rather question is the best way to cope up with the conversational issues. These questions can also be used to develop a fun oriented game especially in the family gatherings and get-to-gathers of the colleagues as well as friends.

In short, a good deep would you rather question can top up the charm of any gathering, even if you are alone, you can ask these kind of funny questions to yourself because your own mind also requires some enjoyment.

Top 100 Deep Would You Rather Questions

We are going to categorize would you rather questions into lists regarding different occasions, personalities, and most importantly, our lists will target the kind of gathering you are in. Therefore, based on our categories and specific targeted audience, you can easily use these would you rather questions to play with the mind of your fellows and friends.

Deep Would You Rather Questions for Couples

Let’s start with deep would you rather questions for the couples because family comes first. For couples, it is essential to get to know each other and especially they must be well aware about the preferences and choices of the other.

For this, would you rather questions are very helpful because you can ask anything by blending it with some unusual aspect. A well-crafted deep would you rather question will surely let get the specific perspective of your partner.


    • If you want to get rid from someone, would you rather break up with him/her or let him/her break up with you? What’ll be your choice?
    • Would you rather choose beauty or money or would you like to have both?
    • Would you prefer marrying to someone who has money and financial resources or you will prefer the one with honesty and less money?
    • Would you rather marry to a person who loves you or you would prefer the one whom you love?
    • Would you rather go after naturally attractive looks or better dressing?
    • Would you prefer a woman with flat body or the one who is bulky?
    • Would you rather consider physical relationship before marriage or not?
    • Would you rather like to have a child at the age of 20 or 40? What will be your choice?
    • Would you prefer living an everlasting life in the poverty or would you choose the shorter life with all of the resources?
    • Would you rather prefer quantity of being loved or quality?
    • What will you disclose if you are given a choice – would you rather disclose your past romances and love life or you will prefer sharing your financial details?
    • Would you prefer giving birth to a baby girl or twins?
    • Would you rather choose adopting a bunch of kids or giving birth to as many as you can?
    • Would you rather sacrifice your love or money?
    • Would you prefer leaving your car or house – if you are stuck in an awkward situation?
    • Would you rather prefer wearing your clothes or going to help for someone who is drowning – assuming you are naked and no one else can help the drowning guy?
    • Would you rather choose being attractive yet poor or you will go for the option of wealthy but ugly?
    • Would you rather wish to fly all around the world with your love or will you choose staying at one place with all the luxuries and awesomeness?
    • If given a choice, would you rather go for the love of your life or wish for all materialistic things that are important and mandatory for the rest of your life?
    • What will be your prefer getting 10 years older or your choice will be getting 10 years younger?
    • Would you rather be single throughout your life or you’ll prefer arrange marriage?
    • Would you prefer online dating or remaining single throughout your life?
    • Would you choose being famous but poor or you will be satisfied with unknown but rich possibility?
    • Would you prefer going to an exotic villa or having sex at the beach?
    • Would you rather prefer living with your best friend or parents?


Deep Would You Rather Questions for Guys

Guys aren’t very dramatic but it is fact that they are entertainment lovers. Deep would rather questions for guys is a hot topic because it’s a way of getting interesting answers from one another.


    • If given a chance, would you rather be a gay or one time sex provider?
    • Would you rather prefer going out with you GF or spending the weekend at home?
    • Would you rather choose an escort or a beautiful gay counterpart?
    • Would you rather prefer watching porno or horror movie?
    • Would you rather do eating at public place or somewhere quiet?
    • Would you rather prefer having a dinner date or a long stroll in the evening?
    • Would you rather go out with your GF at some luxury hotel or on a beach?
    • Would you prefer dating a Milf or a gay?
    • Would you rather go out with your wife’s friend or your ex-GF?
    • Would you rather save your wife or your love from any storm – given the fact that you can save only one of them?
    • Would you rather prefer dating your hot teacher or any college fresher?
    • Would you prefer teaching sex or learning sex?
    • Would your rather like to go on a long drive with your wife or GF?
    • Would you rather choose being physical with the girl of your dreams or the one pretty girl who loves you – you can’t take the option of both?
    • Would you rather choose your parents or your kids for going on a world tour?
    • Would you rather go on the world tour with your wife or with any of your friend?
    • Would you rather like to date your hot neighbor or a decent college fresher?
    • Would you consider a life-long friendship or one year love?
    • Would you rather prefer dancing or sleeping naked?
    • Would you rather consider dating a black chick or white gay?
    • Would you rather sleep with a black hot chic or blonde?
    • Would you prefer dating a hot guy or old creepy woman?
    • Would you rather consider having more time or spending more money?
    • Would you rather prefer sitting in the hotel or lying down on the roof top?
    • Would you rather choose babysitting a baby boy or baby girl?


Deep Would You Rather Questions Game

Would you rather questions are probably the best way to play certain wordy games. You can choose playing these games with your friends, family members, and colleagues.

Therefore, we are going to share some awesome deep would you rather questions games that will help you to play different kind of tricky as well as funny games with your fellows. It’ll surely be a nice way to enjoy the fun oriented moments of the gathering.


    • Would you rather be a beast or drunk rapist?
    • Would you rather become a baseball bat or football?
    • Would you choose cheese or hot dog?
    • Would you prefer eating pizza or drinking alcohol?
    • Would you rather choose play boy film or any Hollywood double X?
    • Would you rather like to watch gay porn or lesbian?
    • Would you like to work in a gay porn film or in a threesome?
    • To impress your boss, would you rather choose a hot drink or cold drink?
    • To celebrate you success, would you rather prefer going on vacation or for long drive?
    • Would you rather choose secretory or your boss for the pleasurable sex?
    • Would you prefer having fun with the sub ordinates or with your superiors?
    • Would you choose a ticket to Disney land or a pass for your favorite bar?
    • Would you rather prefer loving your pet or your boss?
    • If your boss is too strict on you, would you rather choose to kill him or to fuck him?
    • Would you rather prefer having sex in doggy style or just the casual missionary position?
    • Would you prefer being loved or to love someone special?
    • Would you rather consider living for the one who loves you or for the one whom you love?
    • Would you rather choose money or family?
    • Would you rather prefer dating your mom’s hot friend or your father’s GF?
    • Would you prefer a love bite or simple kiss?
    • Would you rather prefer outdoor party or indoor gaming competition?
    • Would you rather choose your emotional side or your intellectual side?
    • Would you rather prefer being boss or the boss of boss?
    • Considering you have to adopt one option, would you rather choose being a smoker or a drinker?
    • Would you prefer adopting a simple yet healthy lifestyle or luxurious but sick life?
    • Would you prefer fun at work or work for fun?


Deep Would You Rather Questions for Girls

Most of the time, it is a bit hard to understand the ultimate demand of girl. Would you rather questions let ask her what you want. Each would you rather question enables you to adopt the best way of asking what you wanna know about the pretty chic.

Ask her different mind tangling would you rather questions to understand her thoughts, views, and ideas about certain aspects of the life. It’ll surely help you to put yourself in a situation from where you can become a man of his dreams.

On the other hand, if you are a girl who wants to make new friends or looking for some creative ideas to have chit chat with her buddies, I would suggest deep would you rather questions to you.


Let’s have a look at some cool would you rather questions.


    • If given a chance, would you rather consider becoming a doll or doll faced?
    • Would you rather prefer a strong lip to lip kiss or a love bite?
    • Would you rather go for hang out with friends or prefer staying low with your family?
    • Would you rather wanna wear makeup or prefer being simple?
    • Would you rather choose a lipstick of dark shade or light shade?
    • Would you consider wearing a hot wardrobe or prefer wearing a simple and sleek dress?
    • Would you rather work in the porn or prefer working in the play boy movies?
    • Would you rather choose a dashing hot black male or a simple white man for your life partner?
    • Would you prefer curly hairs or blonde?
    • Would you rather marry a superhot model or a simple decent household male?
    • Would you rather choose a shiny look or a simple yet compelling look?
    • Would you prefer some social work or any kind of entertainment?
    • Would you rather choose a physical hobby or some non-physical activity for your leisure time?
    • Would you rather listen sad songs or rock music especially when you are in a situation of sorrow?
    • Would you rather choose a Jazz or classic music for your birthday?
    • Would you prefer eating yummy creamy cake or fresh chocolate cake?
    • Would you rather take a cup of hot tea or coffee while you are in the office?
    • Would you rather prefer green tea or coffee?
    • Would you rather choose becoming a thinker or some experiment lover researcher?
    • Would you rather consider yourself a book worm or newspaper nerd?
    • Would you rather feel yourself younger but mature or elder but energetic?
    • Would you rather choose being emotional or cool minded?
    • Would you prefer a starry date or luxury dinner date?
    • Would you rather prefer wearing under garments while going on a date or you would choose going without wearing underpants?
    • Would you rather choose a healthy diet plan or visiting any handsome doctor?