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The Top 50 Would You Rather Questions To Ask Your Crush You Must Try

He knows some questions to ask your crush to make her smile

If you’re looking for a simple icebreaker or an easy way to get a little closer to someone you like, these “would you rather” questions to ask your crush are great. For the most part, they’re silly and playful, which helps to avoid taking things down a serious route.

They can also make for a good laugh, an engaging conversation or anything in between. So versatile and easy to deliver, we just had to put a list together for you to use. Since half the battle is thinking of good would you rather questions for your crush, we’ve put together a list of 50 ideas.

This list has some great options in there no matter what your situation. Whether it’s something that’s freshly developing between the two of you or you’ve been hiding your crush for months.

50 Fantastic “Would You Rather” Questions to Ask Your Crush

Not only are “would you rather” questions for your crush a simple conversation starter, but they’re also easy to answer. Instead of heavy, over-the-top questions like “what do you want from your ideal partner”, you’re giving them two options. Cats or dogs. Mountain top or Times Square. Campsite or luxury hotel room.

What you do with that answer then is entirely up to you, just make sure you have your own answer ready for the question as well. The conversation that comes from “would you rather” questions for your crush usually flow easily. But just in case, having your own answer makes it nice and easy. “Oh really? I’m a dog person because. . .”. Simple!

We’ve taken the time to put this list together with easy “would you rather” questions for your crush — basic, broad questions you can just copy and paste right now. They’re great for getting to know your crush even better! Time to just straight into it!

1. Would you rather a campground in the mountains or a 5-star hotel in the city?

Such a simple way to see what type of getaway they prefer. This can prove helpful later if you want to plan a surprise for them.

2. Would you rather a planned vacation or a surprise vacation?

Some people just really don’t like surprises. It’s better to find out right now than doing it the hard way after weeks of planning!

3. Would you rather watch the sunset or sunrise?

Both can be such a great experience, especially if you make an event of it. Still, some people just aren’t morning people.

4. Would you rather have weird dreams and always remember them or never remember any dream?

This is a silly question to ask your crush that can act as such a great conversation starter. You’ll probably end up with some fun stories of strange dreams they’ve had in the past, which is always amusing. Our mind can be a weird place!

5. Would you rather take a vow of celibacy or a vow of silence?

This can be a great question to ask if you want to leave the door open to your conversation turning sexual. Some people are more sexual than others — you might be about to find out which one your crush is.

6. Would you rather teamwork or flying solo?

Strengths, weaknesses and upbringing can all work together to decide the answer to this one. Some people love to work with a team dynamic, while others are much more comfortable working alone. Do your preferences match up?

7. Would you rather manage rowdy staff or be one of them?

We’ve all be part of “that” team before that would be difficult to manage. The question is, which side of the fence would they rather be on? Do managers get paid enough to handle a rowdy team of co-workers?

8. Would you rather be with a shy person or be with someone that makes you shy?

Being on either side of this scenario can be fun and interesting in their own ways. That rush of being around someone that gives you butterflies can be exciting.

On the other hand, it can be so nice to be with someone that feels that way about you, too.

9. Would you rather someone make the first move on you or be the one who makes the first move?

Find out if they’re the extroverted, assertive type, if they hold onto old-fashioned values or if none of that matters. For some people, the answer might even be “it depends, I don’t think it’s important,” and that’s fine too.

If you’re feeling bold, this question can even be the point where you make that first move.

10. Would you rather work out together or binge Netflix together?

There are couples that love to stay fit together and there are couples who do their own thing then laze about together. Which category does your crush tend to fall into?

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11. Would you rather a fancy restaurant downtown or a campfire meal in the mountains?

This is another great way to tell which type of person your crush is. Do they enjoy living the high life with fancy things or breathtaking views and basic possessions?

12. Would you rather be stylish or comfortable?

Some people value always looking good and wearing high-end brands. Other people are more interested in being comfortable. Do you need to up your fashion game around your crush or are hoodies about to make it into your winter wardrobe?

13. Would you rather work day shift or night shift?

Are they a night owl or an early riser? Some people just aren’t cut out for those 8 a.m. office jobs. Others manage to fit so much in before they even think about heading to work!

14. Would you rather be with someone who needs to have a pet or one who hates pets?

There are so many pros and cons associated with having pets, so this one mostly comes down to priorities and lifestyle. Adorable pets or complete freedom to be spontaneous? This is one of the best questions to ask your crush since it lets you know if they like (or dislike) pets as much as you do.

15. Would you rather wear your partner’s clothes or have them wear yours?

Sometimes it’s fun to throw a silly “would you rather” question for your crush into the mix. Unusual questions like this one call for creative answers or, sometimes, amazing stories. Buckle up!

16. Would you rather someone help you out or figure it out for yourself?

Is your crush fiercely independent or do they prefer to have people around who are willing to lend a hand? It’s great to find this one out early.

17. Would you rather your heart or your head make all the decisions if you have to choose one?

Sometimes, our heart and our head share different opinions. If you had to choose one, which would you let call the shots from here on out? This is a great question to ask your crush!

18. Would you rather have true love or an infinite bank account?

This is another great question to see where their priorities lie. Some prefer the pursuit of money while others find comfort and joy in a partner.

19. Would you rather live in a country that’s always hot or always cold?

Some people just aren’t cut out for one or the other. While some might enjoy sunshine and swimming, others thrive in arctic conditions. What type of country do they like traveling to?

20. Would you rather watch a movie or watch a sunset with your partner?

Indoors or outdoors; how does your crush like to spend their evenings? Maybe even a combination of both? This is one of the good questions to ask your crush since it will give you future date ideas.

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21. Would you rather throw a party for friends or plan a party for friends?

Some people find the pressure of planning a party anxiety-inducing. For others, it’s their time to shine and get creative!

22. Would you rather hit the town on a night out or stay home with a bottle of wine?

Introvert, extrovert or somewhere in between, we all enjoy our social time differently. Ask your crush this question a little early on if you can't tell which type he or she is.

23. Would you rather a big birthday celebration or a low-key experience with close friends?

For some of us, birthdays are an exciting time of year and something to be celebrated. For others, it’s something we dread and never want to make a big deal of. Pay attention to their answer on this one, especially if their birthday is coming up.

24. Would you rather cook a meal with me or order in?

Spending a night in the kitchen can be fun and rewarding — working together and experimenting with your food. Again, Netflix and ordering in is pretty great too, huh?

25. Would you rather be rich or good-looking?

On one hand, being good-looking is said to make it easier to get higher-paying jobs. On the other hand, being rich means you can afford to change how you look. . . the dilemma!

More Flirty “Would You Rather” Questions to Ask Your Crush

26. Would you rather have a great singing voice or have great moves on the dance floor?

27. Would you rather know the date of your death or have it be a surprise?

28. Would you rather get tied up in bed or tie your partner up instead?

29. Would you rather be really early for everything or slightly late?

30. Would you rather have a friend with benefits or a very serious relationship?

31. Would you rather snack on healthy food or chocolate?

32. Would you rather date someone who’s very introverted or very extroverted?

33. Would you rather always cook meals or always order in?

34. Would you rather a kiss on a good first date or leave it for later?

35. Would you rather get a lot of compliments from strangers or only compliments from your crush?

36. Would you rather a coffee date or a date at the bar?

37. Would you rather go out to watch a movie or stay on the couch with snacks?

38. Would you rather hook up with your highschool crush or your celebrity crush?

39. Would you rather a fancy office job or a work-from-home job?

40. Would you rather have a party at your house or go to a party at a friend’s house?

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41. Would you rather date someone much older or much younger than you?

42. Would you rather ask your crush out in person or through text?

43. Would you rather live with your best friend or by yourself?

44. Would you rather a lazy Sunday morning in bed or an active morning?

45. Would you rather talk in your sleep or sleepwalk?

46. Would you rather spill a drink on yourself or on an attractive stranger?

47. Would you rather always use a shower or a bathtub?

48. Would you rather a desk job or an active job?

49. Would you rather a job that makes you happy or a job that pays better?

50. Would you rather bottomless wine or endless dessert?

When to Use "Would You Rather" Questions to Ask Your Crush

These “would you rather” questions to ask your crush are perfect for breaking the ice or getting out of a lull in the conversation. But of course, you don't want to just dive right into asking her when you first see her or while she's talking about something else. You have to ease into these questions and pick the right time. Ideally, it's when she's already talking about a similar or related topic, then you can spring one of these fun questions. It's a great way to be spontaneous and keep her interested.

Whether you’re just hanging out or texting, you can use these questions to get to know your crush better. Who knows, you might just have more in common than you think!


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