30 Would You Rather Questions that’ll Leave You Thinking

Playing “Would You Rather” is a great way to start a slew of conversations at a party, and can even break the ice during a pressure-ridden first date.

The game is simple: you ask someone two impossible-to-answer questions and the rule is that they can only choose one and cannot make up a different answer.

It’s pretty fun when you start asking your friends gross questions, but what about when you’re asking a potential date or a current partner?

Would you rather ask your partner this or that?

The game can get pretty intense, especially when you start asking about personal stuff, but it can also give you and your partner a different medium for getting to know each other.

The trick is to ask something that will encourage them to open up about something personal, without divulging any details. You just pick one answer, and it’s up to you to decide how that plays into someone’s personality.

It doesn’t have to be serious. You can ask someone questions about possible circumstances in your relationship, but it doesn’t mean that it will actually happen. You just want to know what your date would do, if ever they were faced with the situation.

A new twist on an old game

For that purpose, we’ve compiled a list of mind-bending questions that can give you a bit of insight into you and your partner’s thought processes.

Not all of them are serious, but some of them can give you a good read on how your partner will handle your relationship in the long run.

Don’t take the answers entirely to heart, because things can change. Think of this as a fun exercise that will bring you and your partner closer. [Read: 36 random funny questions for flirty guys and girls]

The rules

You can only choose one answer. You can’t say that you would never get caught in that situation. These are fictional scenarios, anyway. Even if some of them are impossible, it’s okay to have fun with the answers.

30 Would You Rather questions

#1 Would you rather eat fast food on all of your dates with a person you like, or eat at 5-star restaurants with a person you dislike?

#2 Would you rather date someone who prioritized looks, or someone who prioritized money?

#3 Would you rather have your partner’s parents dislike you, but accept the relationship, or have their parents accept you, but disapprove of the relationship? (i.e. issues about religion, culture, family background, etc.)

#4 Would you rather take an exhausting and unenjoyable trip to an exotic location for your honeymoon, or have a relaxing time at a dingy motel along the highway?

#5 Would you rather camp out with your partner with only a small survival kit in a beautiful natural location, or camp out in a comfortable RV in a trailer park without any picturesque views?

#6 Would you rather give your partner a cheap and useless gift for every anniversary, or an expensive and useful gift that blows all your savings for every anniversary?

#7 Would you rather play doubles tennis with your partner and your respective exes, or play golf with your respective past friends-with-benefits?

#8 Would you rather have children and raise them without a partner, or have a partner who never wants to have kids?

#9 Would you rather have a threesome with your best friend and your partner, or watch your partner have sex with a stranger, who you will never see again? [Read: Threesome rules – 20 things to know before you even consider one]

#10 Would you rather find a serious relationship on Ashley Madison, or be ghosted by a guy/girl on Tinder?

#11 Would you rather date someone famous and have your life scrutinized by the tabloids, or date a regular Joe and have your life judged negatively by everyone close to you and your partner?

#12 Would you rather wear your pajamas and rollers to a date at a fancy restaurant, or wear something gaudy and controversial to a date at a street-side coffee shop?

#13 Would you rather lie to your partner about the number of people you slept with or tell the truth, but never know how many people your partner slept with?

#14 Would you rather date someone who was intelligent without common sense, or someone who had common sense but is not-so-intelligent? [Read: 17 funny questions to get to know your partner better]

#15 Imagine not being able to get a job that earns more than the minimum wage. Would you rather have a rich partner who doesn’t love you, but will provide for you for the rest of your life, or a poor partner who loves you, but can’t hold a job long enough to pay for your needs?

#16 Would you rather have sex with a person that your partner hates? Or would you rather your partner have sex with someone you hate? Note that you will both find out about each other’s transgressions with either choice.

#17 Would you rather be alone and find true love on the day that you die, or be with someone you can never fall in love with, until the day you die?

#18 Would you rather commit to a serious relationship that has no promises for the future, or have a friends-with-benefits arrangement with someone who wants to marry you after they sow their wild oats?

#19 Would you rather be extremely late the first time you meet your partner’s parents or be extremely early while your partner runs late, thereby leaving you alone with their parents for a significant amount of time?

#20 Would you rather kiss your partner in a lightning storm on top of a hill, or during a sandstorm with no shelter in sight? [Read: 50 relationship questions to test your relationship compatibility]

#21 Would you rather cook a ten-course meal within 3 hours for your partner’s family, or buy them a bunch of unhealthy fast food meals from a questionable establishment?

#22 Would you rather marry someone who doesn’t want to get pregnant/get you pregnant, but is willing to adopt, or marry someone who has extreme problems with fertility, but isn’t willing to adopt?

#23 Would you rather have a long distance relationship because of a job that offers a lot of money and emotional rewards, or have a relationship in the same city with a low-paying job that you can’t leave?

#24 Would you rather gain a lot of weight a few years into your relationship, or have your partner gain a lot of weight instead? [Read: 30 questions for couples to keep the naughty spark alive in the relationship]

#25 Would you rather be single all your life, but have your best friends as company, or be in a relationship, but without any best friends?

#26 Would you rather fall in love with someone you don’t know, or with someone you’ve known all your life?

#27 Would you rather take a risk with someone you don’t trust, or never try anything new with someone you trust?

#28 Would you rather go out into the world to find your true love, or stay inside your shell and never find the one meant for you?

#29 Would you rather love with all your heart and have it broken many times, or not love at all and never get hurt?

#30 Would you rather be with someone you love, or be with someone who loves you?


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