Fun Questions to Ask in the Car
Twenty questions for the passenger seat, short enough to answer while driving and open enough to run for a few miles. Works for a school run, a commute with a friend or a long stretch of highway.
The questions
Open any question for the note
If we could take this road anywhere, where would we end up?
Why ask it
Uses what is already out the window, so nobody has to think from a standing start. It sets a wandering tone rather than a quizzing one, and the answer often shapes the rest of the drive.
What's the weirdest food combination you actually like?
Why ask it
Everyone has one, and the defensive tone people take when explaining it is the entertainment. It also spreads easily: within a minute everyone in the car is confessing something about crisps or cereal.
What's the most useless skill you have?
Why ask it
Self-deprecating and easy, so it works on people who dislike being asked about themselves. Better than asking about talents, because the ridiculous answer is the point and nobody has to sound impressive.
What song do you know every single word of?
Why ask it
Answerable instantly and usually followed by a demonstration, which is a good outcome in a car. It also hands you the next twenty minutes of the playlist without anyone having to negotiate.
What's the strangest thing you've seen out of a car window?
Why ask it
Grounded in the exact activity you are doing, so it prompts real memories rather than invention. Roadside sofas, a horse in a lay-by, someone eating a full dinner at the wheel. Works on any length of journey.
What's the best road trip snack, and what's overrated?
Why ask it
The second half is where the arguments start, which is the point in a car with more than two people. It also frequently ends in a genuinely useful stop at the next services.
What's the strangest dream you remember?
Why ask it
Long-running, which is what you want on a highway, and the teller does not need eye contact to tell it. Notice that people go further with dream stories in a car than they would across a table.
What's a rule you had growing up that you now realize was strange?
Why ask it
Sounds light, then quietly opens the door to family stories. Shoes off, no phone at dinner, a specific chair nobody sat in. Good for a parent and teenager in the same car, because both ends get to answer.
What's the most embarrassing thing you've done in a car?
Why ask it
Narrowed to cars deliberately, which makes it funnier and much safer than the general version. Singing at a red light, reversing into something, an argument overheard at a drive-through window.
If you could be famous for one very small thing, what would it be?
Why ask it
The word small does the work, and it produces better answers than asking about fame outright: the world's best parallel parker, the person who names paint colors. It also skips the usual answer about not wanting to be famous.
What's something you believed for years that turned out to be completely wrong?
Why ask it
Reliably produces the best story of any question here, because the misconception is usually specific and absurd. Children answer this as readily as adults, and the adults' answers are often worse.
What job would you be surprisingly good at?
Why ask it
Surprisingly is the key word: it invites a claim rather than an ambition, so the answer is playful instead of earnest. It often reveals a genuine skill nobody in the car knew about.
What's the best thing you've ever found?
Why ask it
Wide open, and it works because finding something is a story with a beginning and an end. A note in a book, money in a coat, a dog. Good for a lull, because it needs no setup at all.
What's the worst haircut you've ever had?
Why ask it
Concrete and specific enough that people can picture it, and there is always a photograph somewhere. Reliable with a group of mixed ages, since the era of the haircut does half the work.
What would you put in a museum about your life?
Why ask it
Better than asking what someone is proud of, because objects are easier to name than achievements. Expect a bike, a ticket stub, a broken thing kept for no clear reason. It runs long, which suits a highway stretch.
What's a place you'd go back to, and what would you do differently?
Why ask it
The second half stops this becoming a list of holidays. Answers often involve staying longer, going alone, or a conversation someone did not have. It has more depth than the questions before it, so place it once the car has settled.
What's the nicest thing a stranger has done for you?
Why ask it
Changes the temperature of the car without becoming heavy. Answers are usually small and precise, which is why they stick: a lift, a paid bus fare, someone chasing them down with a dropped wallet.
What's something you'd like to be good at by this time next year?
Why ask it
Points forward, and the time limit keeps it modest rather than aspirational. Saying it aloud in a car with someone else in it also makes it slightly harder to abandon, which is not accidental.
What's a question you'd like someone to ask you?
Why ask it
Hands over the wheel of the conversation, which is useful when one person has been asking everything. Quiet passengers often have a very specific answer ready, and it is usually the thing they wanted to talk about all along.
What's been the best part of today so far?
Why ask it
A calm close for the last few miles, and short enough to answer while parking. On a school run, this one gets more than asking how the day was, because it asks for one thing rather than a summary.
Why Car Conversations Work, and How Not to Wreck Them
Practical guidance for the conversation itself
Use What the Car Gives You
No eye contact is the whole advantage
People say more side by side, facing forward, than they do across a table. This is why the school run produces confessions that a sit-down conversation never gets. Do not undo it by turning around to look at whoever is answering.
Ask one question, then let it run
The temptation is to work through a list. A drive is long, and the questions here about being wrong, about a place someone would return to, and about a museum of their life will each fill fifteen minutes if you let them.
Answer first if the car is quiet
Going first with a slightly embarrassing answer sets the level and takes the pressure off. This matters most with teenagers, who will match whatever register you establish.
Let people opt out without comment
A shrug is a complete answer, and pressing it in an enclosed space with nowhere to go turns a nice drive sour. Move to the next question as though nothing happened.
Keep the Driver Driving
- Do not ask the driver anything that requires them to count, remember a list or picture something in detail. Save those for the passenger.
- Go quiet at junctions, merges, roundabouts and anywhere the driver has said they are unsure of the route. Pick the thread back up afterwards.
- Do not hand the driver your phone to look at a photo that goes with an answer.
- In heavy traffic or bad weather, drop to short questions or none at all. Silence is a normal part of a drive.
- If you are the driver and a question is taking your attention, say so plainly and come back to it.
- Nothing that will start a real argument. There is no way to leave the room.
Adjust for Who Is in the Car
School run, twelve minutes
One question, not ten, and preferably the one about the best part of the day or something they believed that was wrong. Interrogation at the end of a school day gets one-word answers no matter how good the question is.
Long drive with one other adult
Start with the food and the useless skill, then move to the museum, the place they would return to, and the stranger's kindness. Six hours is enough time to get somewhere real, so front-load the easy ones.
Full car, mixed ages
Choose questions where a nine-year-old and a grandparent can both answer well: the best thing they have found, the worst haircut, the song they know every word of. Skip anything that needs a career or a decade behind it.
Someone you have just met
Stick to the first six. A shared car ride with a stranger is intimate enough already, and the questions about regret and about being wrong are too much for a first journey.