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Top 50 "Would You Rather" Questions for Guys to Ask Their Girlfriend

He knows the right

“Would you rather” questions are great ways to spice up a conversation with your girlfriend while simultaneously getting to know each other better. The best “would you rather” questions for guys to ask their girlfriend are hyperbolic to the point of ridiculousness.

For example, a classic debate is: “would you rather fight a horse-sized duck or 50 duck-sized horses?”

The point of these questions is to make people laugh, but it should also be difficult to pick an answer. They should refer to bizarre situations that you’d never have to choose between in real life. Be as imaginative as possible, but feel free to play Devil’s Advocate for the other option too. A great “would you rather” can start a debate that lasts for hours.

These questions can get you through a long car journey, a delay at the airport or the queue at the bar.

The worst “would you rather” questions are serious and boring.

  • Don’t ask: would you rather vote for Trump or Biden as president?
  • Do ask: would you rather vote for Spongebob or Squidward as president?

Below, we’ve listed 50 examples of good “would you rather” questions for a man to ask his girlfriend.

These questions will not only make you both laugh, but they should also stir some interesting debate and allow you to discover what type of woman you’re really dating.

The Best 50 “Would You Rather” Questions For Guys To Ask Their Girlfriend

Pick your favorites from this list.

1. Would you rather always wear high heels or always wear slippers?

She most likely puts a lot of thought into her footwear, but will she choose style over comfort for the rest of her life?

2. Would you rather live the rest of your days as an 18-year-old man or an 80-year old woman?

Would she trade her gender for eternal youth? Teenage boys are immature and eternally horny. Elderly women are wise but, well, old. It’s a tough choice.

3. Would you rather be a successful CEO or a stay-at-home mum?

Does she dream of life as a super-successful professional who hardly sees her family or the non-earner who dedicates everything to them?

4. Would you rather lose your Instagram page or lose your best friend?

Most women will choose their besite, but in this era of Instagram addiction, there’ll be plenty who hesitate before answering. If she does, don’t hesitate to call her out for being a #badfriend.

5. Would you rather lose your phone or lose a finger?

Another cheap shot at her social media addiction. Remind her that she can still take the perfect selfie with nine fingers. Her followers would be none the wiser.

6. Would you rather never have no children or 20?

This question will test her desire to be a mother. Yes, many women fear being barren, but is that really worse than having 20 toddlers causing chaos in the house?

7. Would you rather be intelligent and ugly, or sexy and stupid?

Does she value brains over beauty? Which does she think would bring more success and happiness in life?

8. Would you rather be the world’s best singer, dancer or actress?

This question will get her fantasizing about life as a talented celebrity, but what would she like to be famous for?

9. Would you rather be the world’s best singer or the world’s most intelligent woman?

The ability to move the world with her voice vs. the ability to change the world with her intelligence. What would make her happier?

10.  Would you rather become famous for doing a sex tape, or never be rich and famous?

What would she sacrifice for fame and riches? Would she be willing to go down the same route as Kim Kardashian, the world’s most famous talentless celebrity?

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11. Would you rather be forever alone or forever surrounded by people?

No friends vs. no privacy. It might sound like an easy choice for some, but remind her that it’s possible to feel lonely in a crowded room.

12. Would you rather win $50,000 or have your best friend win $500,000?

A true hypothetical test of her friendship and selflessness. How important is money to her?  She’ll tell you that her friend would give her some money, but these are the kind of assumptions that ruin the friendships of lottery winners.

13. Would you rather sleep with Justin Beiber, Jared Leto or Jason Mamoa?

Any questions like this can spark her fantasies and get her in the mood for some bedroom fun with you! Choose three very different celebrities, like in this example.

14. Would you rather date Chris Pratt, Chris Hemsworth or Chris Evans?

The superhero edition of question #13. It's one of the more fun and lighthearted questions guys can ask their girlfriend.

15. Would you rather share your dream celebrity or have an average guy all to yourself?

Would she ditch you to join the harem on Leo Di Caprio’s yacht? You’re about to find out...

16. Would you rather have $1,000,000 and no children, or the average wage and a happy family?

Does money or children equal happiness for her? It’s arguably very important for the two of you to agree on this answer...

17. Would you rather marry a douchebag millionaire, or never wed at all?

Is she OK with marrying a guy she didn’t like, just to take half his net worth in a divorce settlement? Perhaps this is good information to know.

18. Would you rather be married for only five years, or never wed at all?

Would she accept a failed marriage if it at least meant getting her special day? Again, this might be good information to know...

19. Would you rather have a threesome with two women, two guys or neither?

Since you’re already asking fun questions, this could be the perfect time to find out if a threesome could be on the cards one day...

20. Would you rather be able to fly, read minds or have another superpower?

You can learn a lot about a person by asking what superpower they’d choose. Be careful of anyone who would choose mind-reading. They most likely enjoy manipulating people.

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21. Would you rather do OnlyFans and make $100,000 a month, or run a charity and make $1,000 a month?

Is money more important than keeping some things private? Or is making money secondary to a nobler cause?

22. Would you rather live in the desert or the North Pole?

This question will test her ability to look on the bright side for one location or the other. Hopefully, this question will also remind her that she has it pretty good where she’s living now.

23. Would you rather go on an adventure holiday or a lazy beach break?

Fantasizing about her dream holiday will surely put her in a good mood. After she picks one, ask for her dream location. Perhaps you can make a plan to visit one day.

24. Would you rather go a year without pizza or a year without chocolate?

You can replace these two snacks with two of her favorite things. If you’re feeling bold, replace one of them with sex. This will result in either a boosted or a destroyed ego.

25. Would you rather marry a business owner who makes $100,000 a year or be a business owner who makes $1,000,000 a year?

Will she put in the work to be a millionaire or just enjoy the fruits of your labor?

More “would you rather” questions for guys to ask their girlfriend...

26. Would you rather only eat pizza or only eat salad?

27. Would you shave your head or never be able to cut your hair again?

28. Would you rather be unable to orgasm or orgasm every time you think about sex?

29. Would you rather be transported in a limousine or a horse-drawn carriage?

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

31. Would you rather be two feet taller or two feet shorter?

32. Would you rather have 50 boyfriends or zero?

33. Would you rather see into the future or be able to relive the past?

34. Would you rather work as a personal trainer or as a cleaner?

35. Would you rather murder a stranger or all your ex-boyfriends?

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36. Would you rather always fall in love too easily or be unable to love at all?

37. Would you rather be a superhero or date one?

38. Would you rather have the world’s hottest ass or the world’s sexiest boobs?

39. Would you rather be talented but not famous or famous for having no talent?

40. Would you rather be twice as rich or twice as happy?

41. Would you rather have boobs ten times as big or no boobs at all?

42. Would you rather be stranded on a desert island alone or with your worst enemy?

43. Would you rather give up make-up forever or always have to wear it?

44. Would you rather completely lose the ability to laugh or have no-one ever laugh at your jokes?

45. Would you rather make $500,000 a year cleaning toilets or earn minimum wage in your dream job?

46. Would you rather be a genius who everyone thinks is stupid or an idiot who everyone thinks is a genius?

47. Would you rather eat ice-cream every day or never again?

48. Would you rather lose your voice or your hearing?

49. Would you rather lose an arm but have the world’s prettiest face or keep both arms and be considered ugly?

50. Would you rather be repulsed by your own body odor or have everyone else repulsed by it?

Once you have the ultimate list of the best "would you rather" questions for guys to ask their girlfriend, you'll never run out of things to talk about. It's endless fun and laughter when you ask the absurd questions. But it's also a matter of getting to know her better when you ask her some of the more serious questions on this list.


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