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Are you on a first date, but you are running out of things to talk about? There’s no better way to see if there’s a connection between you and your crush than by asking questions.

So if you’re looking for a fun way to test this out, playing “Would You Rather” with flirty questions is an excellent way to go.

👉 If you’re already in a relationship, check out these great Would You Rather questions for couples!

How to Play Would You Rather

Just in case you’re introducing the game to someone, here’s a quick rundown on how Would You Rather is played. Just follow these steps:

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1. Decide on the theme of questions you’ll be asking. Since you’re looking at this particular article, we’re guessing that you’ve already decided to go with flirty questions.

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It’ll just be more fun to follow a particular theme so the questions are similar to one another.

2. Gather around in a circle. A circle is recommended so that it’s easier to see/hear each other.

3. Talk about how the turns will go around. Whether you’re playing with two people or more, this is important in many games to ensure that everyone contributes.

It also relieves the pressure of coming up with questions on the spot.

4. Have fun! Remember that the purpose of playing this game is to get to know one another!

Play Would You Rather Online

The most convenient way to play Would You Rather is playing it online! You can either check out our web app or download our free app “Dilemmaly - Would you rather?” on your iPhone or Android.

Play Would you rather? online

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30 Flirty Would You Rather Questions

Ready for some flirty fun? Let’s jump right into these flirty and sometimes naughty Would You Rather questions to get you started!

1. Would you rather do it with the lights on or off?

Both options can be very exciting and hot.

2. Would you rather be on top or bottom?

This is probably one of those questions that are frequently asked in a relationship. It can tell you a lot about your sexual compatibility with your partner.

3. Would you rather be alone with your crush or have all of your friends around when you’re with your crush?

Sometimes being with just each other, especially for the first time, can be really nerve-wracking. You want to make a good impression, but you don’t want to seem like you’re trying too hard. On the other hand, being around your friends can help take some of the pressure off and allow you to be yourselves. So which would you rather do?

4. Would you rather have your first date indoors or outdoors?

Both ideas could be a lot of fun with the right planning!

5. Would you rather have a car date or a Netflix & chill night?

Car dates are a great way to have some uninterrupted time to get to know each other. But there’s also something really cozy and intimate about cuddling up on the couch with your crush and watching a movie together.

6. Would you rather kiss in public or in private?

This question can actually tell you a lot about how a person is in a relationship. There are some people who don’t mind being affectionate in public, while there are some who are simply against it.

7. Would you rather be stuck on a deserted island or get lost together?

I guess being lost in a city is better than being somewhere far from civilization.

8. Would you rather eat stuff off one another or do roleplay?

One of those dirty questions that could lead to something more. Watch out for the timing when you ask this!

9. Would you rather have a lazy but trusting partner or a jealous but hardworking one?

There’s no right or wrong answer to this question; it simply depends on what you’re looking for in a partner.

10. Would you rather be funny but unattractive or be extremely attractive but boring?

I personally think that being funny is more important because you can never get tired of jokes.

11. Would you rather take morning jogs together or night-time strolls?

Not everyone is a morning person!

12. Would you rather have fancy dinner dates or grand breakfast dates?

This one is tough because both options sound amazing.

13. Would you rather be the funny one or the responsible one in the relationship?

Both traits are important in a relationship. So which trait do you think you’re most likely to possess?

14. Would you rather have a movie date or an adventure date?

Staying in or going out and making new memories together? That’s the underlying question here.

15. Would you rather have your partner maintain a short-hair look or have them grow out their hair?

Either way, having a change in your style is always a good choice.

16. Would you rather have whipped cream or chocolate mousse?

This may seem like an innocent question, but some people may imply a different meaning to it… ;)

17. Would you rather drink wine or beer?

This can tell you a lot about how your partner chooses to unwind.

18. Would you rather have several one-night stands or have a friend with benefits?

Not everyone can answer this question!

19. Would you rather be with a doctor, an athlete, or an artist?

This might induce a fun conversation.

20. Would you rather have lots of kids, just one or none at all?

You might want to save this question for later on down the line. It’s a pretty personal question and one that could potentially lead to some serious discussions about life plans. However, if you’re feeling brave, why not, right?

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21. Would you rather date an introvert or an extrovert?

The mere thought of dating someone different than you is scary, but at the same time, don’t forget that opposites attract!

22. Would you rather listen to your brain or your heart?

This is a great question to gauge someone’s personality. Are they a thinker or a feeler? Do they make decisions with their head or their heart?

23. Would you rather be romantic or practical?

Sometimes romantic people really go out of their way just to keep the fire burning in the relationship. Practicality can also help keep the relationship afloat! It depends on the situation you’re going through.

24. Would you rather date someone who’s more attracted to a person’s looks or their brains?

Did you know that being a sapiosexual is an actual thing? (Go ahead, look it up!)

25. Would you rather end the date with a kiss or with a little bit of mystery?

It’s actually not that common to end the date with a kiss. People are often too shy or too nervous to make the first move. But, then again, if you’re brave enough… Why not take the leap of faith?

26. Would you rather cuddle or kiss?

Are you all about those snuggly bear hugs that make you feel warm and fuzzy inside, or do you lean towards those heart-pounding, butterfly-inducing kisses that leave you weak in the knees?

🤓 Suggested read: 🎄 40+ Trivia Questions To Get Into Christmas Spirit

27. Would you rather win the lottery or find true love?

Here’s the million-dollar question (literally): would you rather hit the jackpot and swim in a sea of wealth, with all your financial dreams coming true, or embark on a quest to find that soulmate who fills your days with love, laughter, and all the warm fuzzies?

28. Would you rather have your dream job or your dream partner?

Career aspirations or heart-fluttering romance? What’s your top priority? Pursue that dream job that lights up your soul, or find that extraordinary partner who sets your heart on fire? The choice is yours!

29. Would you rather have a partner who is dominant or submissive in bed?

Do you crave a partner who takes charge or someone who loves to surrender to your desires?

30. Would you rather be complimented on your looks or your intelligence?

Boost that confidence! Do you thrive on compliments about your stunning looks or prefer being praised for your brilliant mind?

Are you looking for more naughty Would You Rather Questions? 👉 Here’s a list of naughty and dirty Would You Rather questions!

We hope you enjoyed our flirty Would You Rather questions! If you’re craving more fun and excitement, don’t miss out on our ultimate list of 500+ Would You Rather questions! 🎉

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