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Top 50 "Would You Rather" Questions for Women to Ask Their Boyfriend

Making her laugh with some

A “would you rather” question can add some spice to any conversation with your boyfriend. On top of that, you can get to know him better too! These types of questions are meant to be exaggerated to the point of absurdity. Men tend to be particularly partial to lewd and sexual questions. So what are the best "would you rather" questions for women to ask their boyfriend?

A popular question is: “Would you rather have finger-sized nipples or nipple-sized fingers?”

Another is: “Would you rather watch your parents having sex once, or have them watch you 100 times?”

As you can see, most guys have a crude sense of humor, especially when women aren’t around.

But if you can join in with the craziness, they’ll love you even more!

You don’t have to be vulgar to ask a great “would you rather” question. Any question that’s a bit silly can work well, especially if one has to think hard about the answer...

Below, we’ve listed 50 good “would you rather” questions for a woman to ask her boyfriend. Relax, they’re not just smutty examples. We’ve also included questions that can help you find out what type of guy you’re really dating. These are the deep questions that should really make him think.

Either way, these questions to ask a guy can serve to make the time pass while on a long car journey or to make your boyfriend laugh whenever you’re hanging out!

Don’t be afraid to challenge his answer either. If you play Devil’s Advocate for the other side, the debate could last for hours.

The 50 Best “Would You Rather” Questions for Women to Ask Their Boyfriend

Choose your favorites from this list of questions women should ask their boyfriend. They're great conversation starters!

1. Would you rather be a famous porn star, a famous athlete or a famous rapper?

He’ll enjoy any questions that let him fantasize about his dream life. If he chooses porn or rap, ask what his alias will be. If he chooses to be an athlete, probe him on what sport he’d choose to master.

2. Would you rather only eat fried chicken or only eat broccoli?

Will this guy choose a healthy lifestyle over a deliciously unhealthy main course. Feel free to substitute his favorite fast food into this question.

3. Would you rather sleep with 100 supermodels and disappoint them all, or one unattractive woman who thinks he’s a stud?

This question will teach you a lot about selflessness and his desires for promiscuity.

4. Would you rather make a fortune as a toilet cleaner or minimum wage as a rockstar?

This question will teach you whether he thinks money will make him truly happy.

5. Would you rather never drink beers or never watch sports again?

You can replace these stereotypically masculine activities with two of his preferred hobbies if you prefer. If you’re feeling bold, you can add “never have sex” as an option. This will result in an ego boost or an ego destroyed.

6. Would you rather everyone thought you were an ugly nice guy or a handsome asshole?

You'll get to know a lot about your boyfriend and what he values with this question. Don’t be shocked if he chooses to be a handsome asshole. Perhaps he believes “nice guys” always finish last.

7. Would you rather be the world’s worst professional MMA fighter or the world’s best parking lot attendant?

Would he take a beating every few months for the money or the honor of being good at a low-paid job.

8. Would you rather date a woman with no voice or no legs?

It’s the Little Mermaid predicament.

9. Would you rather earn twice as much money or that I earned ten times as much?

Is he comfortable surrendering the breadwinner role? You’re about to find out.

10. Would you rather be a millionaire with no penis or the world’s most well-endowed minimum wage worker?

Does he value money or sex more? You’re about to find out…

11. Would you rather be remembered as the world’s kindest man or the world’s best lover?

What’s his preferred legacy? Be sure to let him know what you would prefer too…

12. Would you rather date Beyonce or Taylor Swift?

It’s OK to let him fantasize about female celebrities. He’ll enjoy it! Use two celebrities who are vastly different for the most interesting results.

13. Would you rather sleep with Kathy Bates in Misery or Toni Colette in Hereditary?

You can also ask him to choose between two celebrities who played some seriously disturbed characters.

14. Would you rather marry your favorite adult actress or your least favorite presenter of The View?

A beautiful young, fit and sexually adventurous woman who sleeps with men for work, versus a middle-aged woman who probably annoys the hell out of him.

15. Would you rather have your own yacht or your own helicopter?

Allow him to indulge in his millionaire fantasies. He’ll thank you for it.

16. Would you rather live with one screaming baby or 20 well-behaved dogs?

Feel free to adjust the question to make a baby seem more desirable 😉

17. Would you rather be unable to orgasm or to always orgasm too quickly?

Let’s put his selflessness to the test once again 😉

18. Would you rather be the world’s most handsome man or the world’s most intelligent man?

Which one does he think will get him further in life?

19. Would you rather have to wear high-heels and make-up at all times or be considered ugly by everyone?

This question gives him a glimpse of what it’s like to be a woman. Am I right, ladies?

20. Would you rather be able to fly or be invisible?

Allow him to choose another type of superpower if he prefers. You can learn a lot about a person by asking what superpower they’d like.

21. Would you rather be 10 feet taller or one foot shorter?

Short men are often overlooked by women, but would being the world’s tallest man present worse problems?

22. Would you rather spend a month in jail or a weekend with my parents?

Ok, this is meant to be used as an ironic question, which shows you appreciate the sacrifices he makes to appease you and your family.

23. Would you rather have your life broadcast on live TV or have everyone forget who you are?

Zero privacy versus complete privacy.

24. Would you rather my boobs were ten times bigger or that I had no boobs at all?

Let’s put his love for big boobs to the test...

25. Would you rather talk through your ass or poop through your mouth?

Sorry, I had to include one more crude one.

More “Would You Rather” questions for women to ask their boyfriend...

26. Would you rather only eat pizza for the rest of your life or never eat it again?

27. Would you rather your most embarrassing and shameful moment made you $1,000,000 on YouTube or never make more money than you’re currently earning?

28. Would you rather be the world’s strongest man or the world’s fastest man?

29. Would you rather do dishes every day for the rest of your life or clean kitty litter every day for the rest of your life?

30. Would you rather have great power and great responsibility or no power and no responsibility?

31. Would you rather sleep with 365 catwalk models per year or one beautiful woman who loved you for the rest of your life?

32. Would you rather be a superhero or an NFL quarterback?

33. Would you rather be a paid hitman or a paid pig farmer?

34. Would you rather murder one stranger or all of your ex-girlfriends?

35. Would you rather fall in love with every woman who was nice to you or never fall in love at all?

36. Would you rather lose both hands or one leg?

37. Would you rather have zero nipples or 100 nipples?

38. Would you rather date the world’s most beautiful woman or the world’s smartest and funniest woman?

39. Would you rather date a beautiful high-maintenance woman or an unattractive woman who never asked you for anything?

40. Would you rather always wear a tuxedo or always wear a tracksuit?

41. Would you rather have a girlfriend who hits you but never complains or one who always complains but never hits you?

42. Would you rather have a girlfriend who’s always happy but never wants sex or one who always wants sex but is never happy?

43. Would you rather make $500,000 yearly working at Mcdonald’s or minimum wage in your dream job?

44. Would you rather live forever as a 90-year-old man or a 19-year old woman?

45. Would you rather die as a hero or live forever as a nobody?

46. Would you rather I slept with the captain of your favorite sports team and got you a lifetime ticket or to never watch them play again?

47. Would you rather sleep with your best friend’s wife or never see him again?

48. Would you rather I made every decision in our relationship or forced you to decide everything?

49. Would you rather be unable to lie or for people to be unable to lie to you?

50. Would you rather be the world’s smelliest man or the world’s ugliest man?

With this list of the best "would you rather" questions for women to ask their boyfriend, you can enjoy a fun, lighthearted conversation with your man while also getting to know him better. Try these out when you're on a long car ride or just hanging out. Who knows what you'll discover about each other!


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