Road Trip! Help me fill the Question Mug.
August 25, 2015 10:02 AM   Subscribe

Multi-hour road trip coming up, and we'd like to fill a travel mug with all sorts of getting-to-know-you types of questions. Personal, non-personal, deep, shallow, serious, hilarious... anything goes. What kinds of questions would YOU ask to pass the time, get to know your car-mates, make memories together, etc.?

We'll take turns passing the mug around and having each person pull out a question and answer it.

In our case, there will be four of us, and we're all family (niece/nephew and two uncles), but you don't necessarily need to filter out questions based on that.

We have other games/activities planned, and the other road-trip-related threads have been helpful, but this one is solely focused on questions.

Thank you!
posted by ToucanDoug to Travel & Transportation (25 answers total) 35 users marked this as a favorite
Since you were born, have you been living or are you dying?

Which rhymes better with orange: peach or grapefruit?

What would you like named after you after you die (i.e., bridge, library, overpass, statue, greenspace, etc.)?
posted by janey47 at 10:04 AM on August 25, 2015 [2 favorites]

Are we there yet?
posted by H. Roark at 10:07 AM on August 25, 2015

If you could only eat one food for the rest of your life, what would you choose?
posted by roomthreeseventeen at 10:10 AM on August 25, 2015

What is the first 'news' event (that is, not something from your personal life) that you remember?
posted by everybody had matching towels at 10:13 AM on August 25, 2015 [1 favorite]

This sounds silly (and slightly creepy?) but I was on a road trip with my brother a few weeks ago and we ended up doing the NYTimes' 36 questions to fall in love and we did NOT fall in love but we definitely bonded; I really enjoyed it.
posted by pretentious illiterate at 10:18 AM on August 25, 2015 [12 favorites]

Describe a perfect day (1) with an unlimited budget and (2) with your actual budget.
posted by craven_morhead at 10:19 AM on August 25, 2015

Is cereal and milk a soup?
posted by Nonsteroidal Anti-Inflammatory Drug at 10:34 AM on August 25, 2015

Would you rather a) only get to eat one food for the rest of your life or b) only get to listen to one song for the rest of your life?

Based on this epic MeTa: What is one fascinating thing about yourself (anecdote, experience, useless talent) that we don't already know about you?

Would you rather date someone who is more attractive than you or who is smarter than you?

Would you rather be funnier than you currently are or smarter?

(That last one came from the Slate Political Gabfest podcast. Each year they do a "conundrums" episode, and it's actually a pretty good source for these kinds of things. Here are some of the conundrums from 2014 and these are some of the ones from 2013.)

Then there are always the classic ones like:

If you could live in any other time period, what would it be and why?

Who is one person, living or dead (real or fictional), that you would want to have dinner with and what would you have for your meal?
posted by litera scripta manet at 11:02 AM on August 25, 2015 [1 favorite]

If you could only listen one album for the rest of your life, what would it be? (Also, only watch one movie.)
posted by The Deej at 11:03 AM on August 25, 2015

Here are a few more of my favorites from the Gabfest conundrums:

Imagine that the night your current significant other proposed to you, they told you that they have a 3-by-3 metal box that you can never open, and you can never know what is inside. Would you continue with the relationship?

Would you give up your smartphone for five extra years of life?

What piece of advice would you give to your 22-year-old self? (Or whatever age seems appropriate based on your ages)

Would you rather have a great job and live in a not-so-great city or a mediocre job in an awesome city?

You're going to eat pie. You can only be guaranteed excellence in either the crust or the filling. Which would you pick?
posted by litera scripta manet at 11:07 AM on August 25, 2015 [1 favorite]

Previously - may be helpful.
posted by lookoutbelow at 11:12 AM on August 25, 2015

"If you could invent a condiment, what would it be?" has been surprisingly effective for lively group discussion in my experience.
posted by babelfish at 11:16 AM on August 25, 2015 [1 favorite]

"If you were a [cookie/ice cream flavour/type of candy] what would you be and why?"
posted by billiebee at 11:31 AM on August 25, 2015

Some of these might be too serious but some might work.

Two-Minute Personality Test
By Jonathan Safran Foer

What’s the kindest thing you almost did? Is your fear of insomnia stronger than your fear of what awoke you? Are bonsai cruel? Do you love what you love, or just the feeling? Your earliest memories: do you look though your young eyes, or look at your young self? Which feels worse: to know that there are people who do more with less talent, or that there are people with more talent? Do you walk on moving walkways? Should it make any difference that you knew it was wrong as you were doing it? Would you trade actual intelligence for the perception of being smarter? Why does it bother you when someone at the next table is having a conversation on a cell phone? How many years of your life would you trade for the greatest month of your life? What would you tell your father, if it were possible? Which is changing faster, your body, or your mind? Is it cruel to tell an old person his prognosis? Are you in any way angry at your phone? When you pass a storefront, do you look at what’s inside, look at your reflection, or neither? Is there anything you would die for if no one could ever know you died for it? If you could be assured that money wouldn’t make you any small bit happier, would you still want more money? What has been irrevocably spoiled for you? If your deepest secret became public, would you be forgiven? Is your best friend your kindest friend? Is it any way cruel to give a dog a name? Is there anything you feel a need to confess? You know it’s a “murder of crows” and a “wake of buzzards” but it’s a what of ravens, again? What is it about death that you’re afraid of? How does it make you feel to know that it’s an “unkindness of ravens”?
posted by zdravo at 11:51 AM on August 25, 2015 [3 favorites]

I like to play a silly version of "would you rather..." where the choices have nothing in common. "Would you rather be a bird or own a silver flute?" "Would you rather be the tongue of a seeing eye dog or be bad at making nachos?"

Some people don't do that well with this, but if you're with creative folks, momentum builds.
posted by mermaidcafe at 2:37 PM on August 25, 2015

There's a fun version that you wouldn't necessarily need to prepare ahead of time, too, called "Black or White" where I am from. You just take turns saying two opposite or related things, and the other person has to say which one they prefer and why. I liked talking about fire/water, coniferous/deciduous, salty/sweet, etc.
posted by shortyJBot at 2:54 PM on August 25, 2015 [1 favorite]

Is a burrito a sandwich? (could turn into an interesting debate)
posted by radioamy at 3:48 PM on August 25, 2015

What are your food quirks? For example, I won't eat cold cheese (it must be melted) and I eat my cereal with no milk. I think everyone has some, even if they initially say they will eat anything. There are often strange/funny stories that go with these quirks.
posted by i_like_camels at 8:58 PM on August 25, 2015

If you could travel in time but only in one direction, would you go back or forward in time?
posted by just_ducky at 9:25 PM on August 25, 2015

If you could have lunch with any one living person on earth, who would it be? Where would you have lunch? What would you eat? What would you ask them? (Can also be asked of historical figures.)
posted by rafaella gabriela sarsaparilla at 5:51 AM on August 26, 2015

Oops, I missed that litera scripta manet asked my question, but about dinner! Though I prefer the idea of lunch, as it's generally a lower pressure meal and I, as a shy person, would feel a little more open to having lunch with impressive people.

So here's another one to make up for redundancy: what was the last thing that you read, place that you visited, or thing that happened to you that changed your mind about something important?
posted by rafaella gabriela sarsaparilla at 5:56 AM on August 26, 2015

What is the movie that people your age would be most surprised that you've never seen?
If you could be in any band, but you had to replace one of the members of that band, what band would you be in, and which member would you replace?
What's your least favorite movie featuring your favorite actor?
Can you do any impressions of famous people?
How long do you think you could hold your breath right now? (How long can you actually hold your breath right now?)
posted by 23skidoo at 6:13 AM on August 26, 2015

The Modern Love essay referring to Arthur Aron's study with 36 questions to gain intimacy with anyone is very good.


If you were on hidden camera, what would people discover about you that they don't know?

What luxury have you been most spoiled by that you can't go back?

If captured, what would the enemy do to you specifically to get you to talk?

What's your favorite way to spend a Saturday?

What is the main thing keeping you from fulfillment right now?

What's something everyone else loves that you think is overrated?

What was the worst job you ever had?

What's the last lie you told?

What's the best/worst advice you've ever gotten?

You're on The Moth tomorrow. What's your story?

What's the worst thing someone could say during sex?
posted by reksb at 10:14 AM on August 26, 2015

Thanks, everyone! These are fantastic!!! I hope this list provides many more with fruitful roadtrip conversations.
posted by ToucanDoug at 11:43 AM on August 27, 2015

Name the top five people, living or dead, you'd like to have a beer with.
posted by raider at 10:31 AM on September 6, 2015

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