Would You Rather…

Whenever Alex and I are on a trip—on a plane, on a train, out to dinner, at the beach—we end up playing “Would You Rather?” It’s random and entertaining…and it also can reveal funny things about the other person (someone you thought you knew until he admitted he’d rather have the power of invisibility vs. flight what is he crazy!!!)

Some sample questions:
Would you rather be lost in a desert or at sea?
Would your rather make more money or get more vacation time?
Would you rather meet your ancestors or your great-grandchildren?
Would you rather take a vacation to a city or the beach?
Would you rather be an amazing cook or an amazing dancer?
Would you rather camp or stay in a hotel?
Would you rather always be a little too hot or a little too cold?

The game invariably spirals into other questions, such as: Who would you invite to have dinner with us tonight (if you could pick anyone*)? Where would you go on vacation tomorrow if money were no object? What are you bad at that you wish you were good at? Describe your dream house.

Do you ever play this game? Any other little rituals you have in vacations?

P.S. A great thing to do on romantic vacations, and our first trip without babies.

* Tina Fey!

  1. NICOLE K. says...

    One that I can NEVER decide on is “Would you rather have brown teeth or a 1-inch forehead?”

    • Joanna Goddard says...


  2. My sister explodes my brain with this game. So i started inventing even more insane scenarios “would you rather be a jelly-fish dehydrating in the sun, or a camel in Antarctica?” would have to be my finest. :p

  3. Would you rather be given $100,000 in cold hard cash or $1,000,000 to spend on Amazon?

  4. I love this game! Play it sometimes on dates when we get a bit bored and lose the conversation thread. We usually add an IF part to the beginning, like IF you were a hollywood star, would you rather date megan fox or natalie portman? And etc :) So many variations!

  5. Just a quick comment to say you look stunning in this photo. Have a great weekend!

  6. Once on a road trip with family, I began texting questions to a guy I was getting to know. I asked first, since he was not trapped in a car with nothing to do as I was. He was game, and I plied him with one after another: Milk or dark chocolate? Ballet or opera? Harley or Ducati?

    It was surprisingly enlightening! Some answers were not at all expected, but others were. It can tell you a lot about the person if you ask good questions. As a bonus, you also learn more of their favorite things!

  7. I play this all the time with my kids, so fun!

  8. I used to play this all the time as a kid and I still remember one that ended the game for us. I was in 5th grade at a sleepover party and the question was “Would you rather eat glass or stand naked in a store front for a day?”. When that got asked we all agreed that there was no topping that and we stopped playing. Hahaha.

  9. I never post comments – but I just have to tell you how absolutely beautiful you look in your photo!

  10. I am dying at some of the questions in the comments! I’ve never played this game before, will have to try it!!

  11. mw says...

    I teach second grade, my kids play this all the time. In fact we incorporate it into math now! Question. Survey. Graph. Conclusion.

  12. mw says...

    I teach second grade, my kids play this all the time. In fact we incorporate it into math now! Question. Survey. Graph. Conclusion.

  13. Our road-trip game is each person taking turns to state a line from a song (careful- no inflection!), with everyone else trying to guess the song.

  14. Would you rather …

    – Have uncontrollable hair or uncontrollable arms?
    – Be naked for a day in front of everyone you know, or have to spend a year in a place where you know no one?
    – Be really itchy for one year, or always have a runny nose?

    Love this game … but, as you can see, we tend to the absurd!

  15. Would you rather …

    – Have uncontrollable hair or uncontrollable arms?
    – Be naked for a day in front of everyone you know, or have to spend a year in a place where you know no one?
    – Be really itchy for one year, or always have a runny nose?

    Love this game … but, as you can see, we tend to the absurd!

  16. I often play games like that with my family when we are at dinner or on vacation, but our typical questions are “What are your top five places you want to go?” “What five people would you pick right now to be your bridesmaids?” etc. My mom and I like to play this game when we are at airports or just waiting around somewhere where the fifth guy to walk by is my husband, etc. It’s silly but fun!

  17. Thank you! Sometimes, honestly, we run out of things to talk about on date night because we are together so often. I’ll use these!

  18. These are such good questions. I’m going to keep these in mind :)

  19. I pride myself on having the GROSSEST would you rather ever. Everyone hates it and can’t choose:

    Would you rather eat a bucket of scabs or a drink a bucket of spit?

    UGH I’m cringing.

    Maybe don’t use that one out on your dinner date:)


  20. lo says...

    I love this, especially since your questions are so positive! I often think of this game as choosing between horrible things (like would you rather have no legs or no arms), so it’d be amazing if you posted even more of your questions!

  21. Just asked my boyfriend all these questions, we especially liked the meet your ancestors vs great-grandchildren one. We both chose ancestors

  22. Ok me and my best friend have played this game since we were in high school. hahahaha we still do , we’ll send each other “Would you rather’s” texts at random times.


    • Do you have any particularly (not gross) questions, Myrna?

  23. My husband and I play a very similar game on road trips, but our two options are always horrible. For example: you can fly, but only 2 feet off the ground OR you can fly, but it’s as physically taxing as running. Which would you choose?

  24. Me too Tina Fey! Ir Barack Obama. If I could be better at anything I would want to be better at math. It’s just embarrassing how long it takes me to calculate tip.

  25. I haven’t played this game before. But your sample questions was so much fun, so I decided to answer them over at my blog. I also asked my viewers to play along! I hope some do. hehe.

    If you want to answer them as well, you are welcome ;)

    (ps, It was harder than I thought to come up with good answers)

  26. Love this game but we always go WAY way more crude or funny or weird.

    A couple of my favorites:

    Would you rather be a tree, watching the world from a single spot or never spend the night in the same place for more than one evening?

    Would you rather have one nostril or one eyebrow (non pluck-able)?

    Would you rather have farts that always cleared a room (smelly) or ones that came out in visible colors?


  27. we have a friend who does would you rathers all the time–on ski lifts, in text messages, at a bar, anywhere!–the one we always ask people is ‘would you rather be the bearded lady (and even when you shave it comes right back) or the giant?

  28. Love this game but it devolves quickly…especially when you play with a bunch of teenagers! It’s always a great car game for youth group trips, but I’ll never forget the time
    One of my interns asked me if I would rather punch an old lady in the face or drown my child’s puppy in front of her eyes…and then he was shocked that I picked the old lady!

  29. This game is the best. My friends and I play with more slightly twisted questions, and the choices are often unrelated. Like… would you rather have toes for fingers or live and work in places with no windows?

    Also – in terms of special power, I will always choose teleportation, over invisibility or flight or anything. I love traveling but I HATE the process of getting there! Can you imagine just popping in to visit your mom or your best friend even if they live hundreds of miles away? Not only could you go anywhere in the world in an instant, but you’d never miss a birthday, holiday party – anything!

  30. Funny Story: My family plays this game but also plays a game where you say something nice about the person to your left. Well, the other night, we were playing the latter and my youngest boy (3) was confused and kept saying “Daddy, would you ratter fight a snake or fight a bewr?” while the rest of us were saying things such as “you are a great mom” or “you have awesome hair”…

    • Carol F. says...

      LOL So cute.

  31. My sisters and I ALWAYS play this! Our questions always start normal, like the examples you provided,and then things get really weird. My favorite all-time question:

    Would you rather have Cheeto fingers (that cheesey film on your fingers after eating Cheetos) FOREVER or have to wear a nose ring with a chain that connected to your earrings (!?) for the rest of your life?

    Hard choice, right??

  32. My friends and I always play “would you be friends with me if…I had a permanent poppy seed stuck in my teeth” and other lovely scenarios. We always get creative.

    P.S. love your hair long!

  33. yep. our version also gets dark or dirty pretty quick! and when that happens and you don’t want to chose either option we always add the caveat- you HAVE TO chose one or else you get both.

  34. Ever since I was a kid, we would always play a game on long car trips called “What’s your favorite?” it starts off with ice cream flavors but ends up being “What’s your favorite poisonous animal?” or “What’s your favorite epidemic?” haha. We would also imagine certain famous people coming to dinner and what we would serve for dinner. If we didn’t like them, we’d just say “stale bread.” hahaha

  35. This is so great! I’m definitely trying this out with Boy next date night :) xx

    Katy | <a href=”></a>

  36. we always end up playing “kill, sleep with, or marry.” my favorite is to turn it literary and make people choose from anna karenina, elizabeth bennet, and anne of green gables.


  37. So fun! We often play the “Movie Game” when we’re in the car on a road trip – usually with more than 2 people. You alternate between naming movies and actors based off who has been in which films. It can get so competitive!

  38. Love this game! It’s always so interesting to learn the reasons behind people’s answers!

  39. This TOTALLY reminds me of a moment from last week where I questioned everything I ever knew about my husband. We found out some craaaazy/secret info about one of his life long friends. I said “Well, would you rather see him…… or…….” and my hubby’s answer blew. my. mind.

    I kind wish I hadn’t asked!

  40. We play Twenty Questions! Usually with hilarious things that have happened so far, which makes it even better.

  41. Whenever my husband and I are at a loss of what to talk about, we lapse into dreams. Usually we describe what we’d do if we won the lottery (or if we made tons of money – a pipe dream since we’re both still in school). It’s always interesting to see how things change as we grow. We used to be strictly concerned about getting a big house and going on a long vacation, now we focus on paying off our debt, and supporting our families.

  42. You should check out the This American Life someone referenced above. It will give new insight to Alex’s decision to be invisible rather than fly :)

  43. A really fun game to play in groups is one person says “Who is the most likely to ____” and then says “1, 2, 3” and then everyone points to the person they think at the same time. You count up who got the most and then they can ask one person why they picked them. Then the person picked asks the next question. Complicated? It’s really a blast. And tells you a lot about what people think about you! Also, a great way to involve everyone over.

  44. Love this! My BF and I tend to play when a boring TV show is on and talking to each other is more entertaining.

    We also like: what would you do for a million dollars that you wouldn’t do for a thousand dollars?

  45. i love this! and i found out a few things about myself just answering these questions really fast, with no time to think :) i may start using it on roadtrips! :)

  46. Seems to be more than a game. The only quest I could answer for sure
    …I would rather stay in a hotel.

  47. What a great idea! I am going to play this with my husband on our trip this weekend.

    I gotta say Jo, the quality of the posts this week has been excellent (of course it’s always great) – there are some really interesting topics!

  48. I always want to play this game but MY boyfriend is opposed! He “doesn’t like to answer hypothetical questions”!!!

  49. I think I agree about choosing the power of flight, actually! :-) But yes, I play this all the time. One of our favorite cafes in the city actually has a board game version of it!

  50. E. says...

    we do “what would you do if you won the lottery” a lot… :)

  51. This is fantastic! My husband and I are going on a road trip this weekend with another couple. I’ll definitely pull this out for those boring moments in the car!

  52. We play a similar game called ‘Top 3.’ Each person takes a turn asking a question and the other person answers with their top 3 choices ie.

    ‘What are your top 3 dream jobs?’ ‘What are your top 3 favorite chocolate bars?’
    ‘If you could live anywhere, which 3 places would you choose?’

    It always makes for interesting conversation!

  53. I love would you rather!

    Ours always ends up very bizarre… would you rather always have to walk around with potato salad in your shoes or would you always have to sit in a chair made out of sandwiches and always be getting mustard on your pants?

    Tough call.

  54. what a great idea! we’re roadtripping to Newport RI from NYC this weekend, and these will definitely help pass the time as we drive up through inevitable NYC/CT rush hour traffic…

  55. When we went to Italy for the first time together we made a scavenger hunt (ex. sophisticated man in a suit eating gelato, a broken side-view mirror on a car (TONS of those)). It got quite competitive as their were prizes involved. Keeps you looking at your surroundings. Obviously, this works best in a place that is less familiar.

  56. Ha – I love this. The British series Extras with Ricky Gervais has the characters playing this game all the time. They take it one step further with ridiculous ‘would you rathers’ such as ‘would you rather die of the cold or of the heat’ or ‘would you rather wake up and find your teeth have fallen out or your hair has fallen out’ – hilarious.

  57. hahaha lucy i know what you mean, it can turn dark pretty quickly :)