30 Hilarious and Steamy Would You Rather Questions

Playing Would You Rather is a fantastic icebreaker with a guy you just met, and it's equally great for shaking things up in an established relationship. Keep it lighthearted with a funny would you rather question, or steer it somewhere much dirtier — the choice is yours. If either sounds appealing, keep reading.

Would You Rather works by giving your guy two options to choose between. He has to commit to one — no picking both, and no dodging by refusing to answer. That would defeat the purpose. Make it clear upfront that there are no wrong answers. Once he picks, you can dig into a funny, thought-provoking, or downright sexy conversation. Bonus: if the question centers on something sexual he'd want to do, you've got a built-in activity once the game wraps up.

You can also pair this Would You Rather game with a drinking game. Jot down what you predict he'll pick before he answers. Guess right, and he drinks. Guess wrong, and you do. As the evening progresses, expect the questions to get sillier, wilder, and more sexually charged.

More: 22 great drinking games for 2 people.

Keep in mind that even though these answers are meant for fun, they can end up being surprisingly revealing. Your guy might open up about what he genuinely thinks when you pose a question this way. It's often an easier route than asking him something directly, especially for those trickier topics you might normally avoid bringing up. The playful setting changes the vibe, and he'll likely feel more at ease since it's "just a game."

Remember: there's no right or wrong answer here, and judging him defeats the purpose. That said, his responses to questions like these can offer a hint about whether he's a good match for you.

Here's a mix of funny would you rather questions and sexy would you rather questions to try out:

1. Would you rather sit through dinner with my parents or quit Facebook for an entire week?

2. Would you rather chow down on a Carolina Reaper, the world's hottest chili pepper, or swap your toilet paper for sandpaper?

3. Would you rather bundle up in your heaviest winter coat during peak summer heat or wear nothing but a swimsuit in a snowstorm?

4. Would you rather have a head the size of a watermelon or the size of a tennis ball?

5. Would you rather have your boss walk in on you dancing in the mirror or picking your nose?

6. Would you rather travel backward in time to alter history, or forward to see what's coming?

7. Would you rather go a full year without beer or a full year without television?

8. Would you rather stand 4 feet tall or 8 feet tall?

9. Would you rather have the power of invisibility or the power of flight?

10. Would you rather be a vampire or a werewolf?

11. Would you rather always give terrible advice or always receive terrible advice?

12. Would you rather deal with partial hearing loss or a growing bald spot?

13. Would you rather suffer through a week-long hangover or bring me to dinner at your parents' place?

14. Would you rather understand every human language or be able to talk to your dog?

15. Would you rather pocket a guaranteed $100,000 or gamble for a 50-50 shot at $1 million?

16. Would you rather be attractive but end up with an unattractive spouse, or be unattractive and marry someone gorgeous?

17. Would you rather sleep with someone who has terrible breath or someone with body odor?

18. Would you rather be a butch woman or an effeminate man?

19. Would you rather give someone a foot rub or receive one?

20. Would you rather have sex with a sheep with nobody ever finding out, or never touch a sheep but have everyone assume you did?

21. Would you rather stick with one sexual partner for life, or have several partners but never settle into a relationship?

22. Would you rather be watched while having sex, or be the one watching someone else have sex?

23. Would you rather have an open relationship where you both sleep with other people, or would you rather have threesomes together?

24. Would you rather watch me have sex with someone else, or be the one making out with a different person while I watch?

25. Would you rather be a peeping Tom or a flasher?

26. Would you rather have me pee on you, or would you rather pee on me?

27. Would you rather be wealthy with a small penis or broke with a large one?

28. Would you rather give up masturbating or give up oral sex for good?

29. Would you rather have me read erotica out loud while we touch ourselves, or watch porn together?

30. Would you rather only ever have sex in the bedroom, or only ever have sex everywhere except the bedroom?

The beauty of Would You Rather is that it opens the door to topics that rarely come up in normal conversation. You might ask something and get a completely unexpected answer.

Another perk is that it keeps the conversation flowing between you two. Sure, things might start off goofy, especially with a funny would you rather question, but that early back-and-forth is exactly how you get to know your guy better. Every exchange about his preferences and reasoning builds a stronger connection.

These questions give you a low-pressure way to explore what you each enjoy and don't enjoy. Bringing up bedroom preferences directly can feel awkward and nerve-wracking, but answering inside a game makes it feel far less loaded. This guide to sexual communication can also help make those conversations easier.

Mixing funny would you rather questions with sexy would you rather questions keeps the mood light and playful throughout. Once you're both cracking up over the ridiculous scenarios, you'll naturally feel more connected and at ease. You might even end up closer afterward, especially if you both let slip something you'd been keeping under wraps.

Would You Rather is a great game, but don't lean on it constantly or it'll wear thin. Rotate it with something like these Truth or Dare questions every so often. Bring it back out whenever you're both bored and looking for something fun to do together.

April 11, 2021