25 Original Would You Rather Questions To Ask Your Crush To Spark Conversation

You probably never even consider playing Would You Rather with someone you’re dating, but why not? It’s a great way to get to know someone and some of the answers can be hilariously illuminating. However, you don’t have to go with the same old boring questions. If you want some genius Would You Rather questions to really stump your date or just need a conversation starter, we’ve got just the thing for you.. A lot of these can be changed or adapted for your personal situation, so have fun and pay close attention to what they say.

  1. “Would you rather die in 10 years with no regrets or live 30 more with a lot of regrets?” When we said hardest Would You Rather questions, we meant it. Let your crush define what they would like their life to look like.
  2. “Would you rather meet one of your ancestors or meet your future children?” Do they think more about the past or the future? If they chose one of their ancestors, ask which one it would be and why to continue the conversation.
  3. “Would you rather know when you die or how you die?” Do they fear death or fear never achieving all of their goals more?
  4. “Would you rather be able to teleport or to fly?” You can find out how they prefer to travel!
  5. “Would you rather have someone framed for a crime you committed or go to jail for a crime you didn’t commit?” Test your crush’s moral values with this tough question.
  6. “Would you rather live off-the-grid or in a house with 15 people?” Do they lean towards introversion or extroversion?
  7. “Would you rather turn into a rat every time you sneezed or an elephant every time you coughed?” Swap out with different animals and symptoms as desired.
  8. “Would you rather lose the ability to read or the ability to hear?” How would they adapt?
  9. “Would you rather be your last or first Halloween costume?” Basically, would they rather be something cute and tiny or maybe something silly or raunchy for the rest of their lives? You can also ask for pictures to prove that they dressed up as either of these options.
  10. “Would you rather kiss your worst enemy or a rabid fox?” Do they drop grudges or risk their own safety to avoid their enemy?
  11. “Would you rather get a cold every week or have chicken pox every month?” How would they cope with either?
  12. “Would you rather be followed by 100 baby ducks or 10 baby elephants?” This one could be easy if one of them is their favorite animal. But it’s also funny to see how they would adjust to everyday life with their chosen group of animals.
  13. “Would you rather eat your favorite food every day or watch your favorite show every day?” Food versus entertainment: which one wins?

More questions to ask

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  1. “Would you rather make a candle out of earwax or a sculpture out of boogers?” Yeah, gross. But the justification of their choices is what makes it creative and funny to hear.
  2. “Would you rather live in a world without your favorite food or your favorite color?” What matters more to your crush? Though it would be hard to know which mattered more if you never knew either existed to begin with. Still, it’s worth learning more about why they choose what they choose.
  3. “Would you rather have more time to pursue your hobbies or more pay?” What do they value more in their own life? You can see if they like to pursue passions or their ambitions. This can be really hard particularly if they value both and don’t want to have to choose!
  4. “Would you rather have a massive family you don’t really speak to or two close friends?” Where do their loyalties lie strongest? This might be easier for them to answer than you might think, especially if they’re closest to their chosen family.
  5. “Would you rather be haunted by a ghost or abducted by an alien?” Explore this one if either of you believe in life after death or life outside of Earth. This is a really hilarious question to ask as well, especially if it gets you talking about little green men.
  6. “Would you rather have no money or no possessions?” Would they be the kind of person who is a minimalist or a maximalist?
  7. “Would you rather bring back ’20s or ’90s style?” Swap with other decades or even fashion from other cultures for more fun.
  8. “Would you rather have a lifetime of food or a one-time opportunity for a free $200,000?” Another question concerning little pleasures versus cash money.
  9. “Would you rather do 100 pushups or 100 lunges?” Or, would you rather miss leg day or arm day? This one is great for gym enthusiasts, so hopefully you like hearing about elaborate workout routines.
  10. “Would you rather marry someone you’ve known for a day or never marry at all?” Sneakily get insight on their stances on love and marriage…and if you have a chance of being their spouse someday.
  11. “Would you rather wear pants that are too tight or shoes that are too big?” Which is the biggest inconvenience for them?
  12. “Would you rather be born 1,000 years ago or 100 years into the future?” You can change the year amounts to further expand upon the possibilities.
Sassy with a little bit of sweet, if you're lucky. Obsessed with MUA channels and astrology TikTok.