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Browse Travel Dilemmas Would You Rather questions

76 questionsFree to playUpdated weekly

Showing 1–50 of 76

#1 · Would you rather
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A) book the trip in peak season at double the price B) book it off-season with half the city shut
Good one?
#2 · Would you rather
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A) eat the same safe meal all trip B) order blind and finish it whatever it is
Good one?
#3 · Would you rather
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A) have your gate move to the far end of the airport B) have the flight sit four hours at the right gate
Good one?
#4 · Would you rather
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A) get the hotel room facing a wall in total silence B) get the one with a view over a loud street
Good one?
#5 · Would you rather
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A) sit beside someone who takes their shoes off in flight B) sit beside someone coughing the whole way
Good one?
#6 · Would you rather
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A) check out of your hotel at ten and drag your bags around B) pay half a night to keep the room until four
Good one?
#7 · Would you rather
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A) go back to the country you loved and find it completely changed B) never go back and keep it perfect in your memory
Good one?
#8 · Would you rather
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A) stay in a hotel where the AC roars all night B) stay in one with no AC and windows that don't open
Good one?
#9 · Would you rather
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A) book the hotel with great photos and grim reviews B) book the plain one everyone quietly recommends
Good one?
#10 · Would you rather
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A) learn your flight is cancelled while still at home B) learn it after two hours in the security line
Good one?
#11 · Would you rather
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A) land at 6am and wait until 3pm to check in B) check in at once and pay for a night you never slept
Good one?
#12 · Would you rather
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A) get your visa approved an hour before takeoff B) apply months ahead and pay four times as much
Good one?
#13 · Would you rather
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A) share an airport taxi with a driver taking the long way B) wait an hour for the train that costs nothing
Good one?
#14 · Would you rather
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A) have the seat in front recline onto your knees all flight B) keep yours upright the whole flight for the row behind
Good one?
#15 · Would you rather
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A) sit on the tarmac two hours before takeoff B) sit two hours on the tarmac after you land
Good one?
#16 · Would you rather
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A) know the whole trip in advance B) be surprised by all of it, good and bad
Good one?
#17 · Would you rather
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A) sit next to a screaming baby on every flight B) sit next to someone who won't stop talking to you for the whole flight
Good one?
#18 · Would you rather
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A) spend the last night at the airport to save a hundred B) pay for the hotel and leave at four in the morning
Good one?
#19 · Would you rather
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A) board the flight last with no overhead space left B) board first and wait forty minutes in your seat
Good one?
#20 · Would you rather
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A) sit at the window with a seat that will not recline B) sit on the aisle beside someone who never stands up
Good one?
#21 · Would you rather
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A) carry every ticket and passport for your group B) carry none and ask for yours at every desk
Good one?
#22 · Would you rather
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A) queue two hours at the car rental desk after landing B) take three buses to the hotel instead
Good one?
#23 · Would you rather
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A) queue twenty minutes for the plane toilet B) hold it until landing and taxi for thirty more
Good one?
#24 · Would you rather
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A) always arrive at the airport three hours early B) always arrive with four minutes to spare
Good one?
#25 · Would you rather
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A) take the trip now and not be ready B) wait until you are ready and never go
Good one?
#26 · Would you rather
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A) take off into turbulence you feel in your teeth B) wait out a six-hour weather delay at the gate
Good one?
#27 · Would you rather
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A) answer work messages from the beach B) go offline and come back to the mess
Good one?
#28 · Would you rather
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A) spend the whole trip fighting brutal jet lag B) arrive rested but a day late and miss the first thing you booked
Good one?
#29 · Would you rather
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A) eat airline food you cannot identify B) go fourteen hours on one pack of pretzels
Good one?
#30 · Would you rather
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A) spend your whole travel budget on the flight B) spend it all once you land
Good one?
#31 · Would you rather
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A) book nothing and figure the whole trip out when you land B) book every detail and never change your mind
Good one?
#32 · Would you rather
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A) travel the world but never stay anywhere longer than one night B) see only one country for the rest of your life
Good one?
#33 · Would you rather
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A) be a tourist and see all of it B) blend in and see almost none
Good one?
#34 · Would you rather
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A) the window seat on a long flight and no getting up B) the aisle seat and everyone climbing over you
Good one?
#35 · Would you rather
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A) lose your passport on the first day of a two-week trip abroad B) lose the phone that has every booking, ticket and photo on it
Good one?
#36 · Would you rather
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A) move somewhere new every year B) stay put and watch everyone else go
Good one?
#37 · Would you rather
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A) pack everything you own for every trip and carry it all B) travel light and always need exactly what you left at home
Good one?
#38 · Would you rather
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A) have unlimited money to travel but only two days off a year B) have unlimited time off but barely enough money to leave your own country
Good one?
#39 · Would you rather
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A) be the one who plans the whole trip B) be the one who never gets a say
Good one?
#40 · Would you rather
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A) sleep the whole flight and miss the view B) see everything and land wrecked
Good one?
#41 · Would you rather
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A) travel with someone who books every hour B) travel with someone who books nothing
Good one?
#42 · Would you rather
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A) a home you never travel from B) a life lived out of a suitcase
Good one?
#43 · Would you rather
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A) understand every language but never taste local food again B) eat incredible food everywhere but never understand a word said to you
Good one?
#44 · Would you rather
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A) give up your seat so a couple can fly together B) keep it and feel their eyes for eleven hours
Good one?
#45 · Would you rather
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A) say yes to the last-minute detour on the trip B) keep to the plan and always wonder
Good one?
#46 · Would you rather
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A) photograph the whole trip and half-live it B) live it fully and come home with no photos
Good one?
#47 · Would you rather
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A) travel anywhere in the world for free but always completely alone B) always travel with the people you love but pay double for everything
Good one?
#48 · Would you rather
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A) tell everyone about the perfect place you found abroad B) keep it secret and always travel there alone
Good one?
#49 · Would you rather
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A) lose a day to the border queue B) skip it and never learn why they stopped you
Good one?
#50 · Would you rather
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A) get upgraded to first class on a two-hour hop B) be stuck in economy on a fifteen-hour flight
Good one?

About travel dilemmas dilemmas

Agonizing travel Would You Rather questions — flights, layovers, lost luggage, border queues and jet lag. Both options hurt. Perfect for the airport gate, the road trip and anyone stuck between two bad itineraries. Every question below shows the live global split once you pick a side, so you can find out whether your take is genuinely rare or whether half the internet agrees with you. Nothing is behind a sign-up, and the questions are free to read out loud, print, or play on a big screen.

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