Every friendship has a few questions nobody asks. What you really thought of their ex. Why you actually cancelled in March. Which of you always gets their way and pretends not to. Search for "uncomfortable questions to ask friends" and you will find hundreds of them, with almost no advice on how to ask one without the room going quiet. The trick that works, especially in a car, is not to ask the question at all. Get everyone to guess the answer. That is how What Would I Say? plays in MileSmile, and three new decks point it at the questions people avoid.
How the game works
One person is in the hot seat. The app reads out a question about them, say "What is the fake excuse I use most to get out of plans?" Everyone else guesses, out loud, what that person will say. Then the person in the hot seat gives the real answer.
That is the whole game. No score sheet, no board, nothing to set up. What makes it work is the order: the guesses come first and the truth comes last.
Why guessing makes a hard question softer
Ask someone straight out what their pettiest grudge is and you have put them on the spot. They have to decide, in front of everyone, how honest to be, and most people play it safe. Ask the car to guess instead and the pressure moves. For most of the round the person in the hot seat just listens while other people stick their necks out. By the time the real answer is due, the car has already said four wilder things than anything they were about to admit, and the truth sounds mild by comparison.
The guesses are also the fun part. Being guessed wrong is funny. Being guessed right is slightly alarming, and also funny. Either way you learn something about how your friends see you, which is often more interesting than the answer itself.
And a turn order changes the mood. A question that would feel like an ambush over dinner feels like a round of play when there is a hot seat and a reveal. The format gives people permission to be a little bolder than they would be in plain conversation, and that is the only reason deep questions like these get answered at all.
Three decks for the questions people avoid
These are the questions people skip because they sound like trouble. Each deck is written for a different group, and none of them is out to shock anyone. They are about the things everybody half knows and nobody says.
Skeletons in the Closet, for friends
Skeletons in the Closet is for friends who think they already know each other: old grudges, secret opinions, the thing you never admitted. "What would I say is the pettiest grudge I still hold?" gets a groan and then a very specific story about a birthday in 2019. "What opinion do I keep to myself just to avoid an argument with you lot?" usually starts the argument it was avoiding. That is fine. You are in a car, and nobody can storm off.
Things We Don't Say, for couples
Things We Don't Say is for two people who share a home, a calendar and a short list of subjects they keep stepping around. Small resentments, secret wishes. If you have been looking for uncomfortable questions to ask your partner, these are gentler than they look, because your partner has to guess first. "What do I apologise for only to end the argument?" lands very differently as a guess than as an accusation. "What would I say is the thing we are both avoiding talking about?" is one to save for a long, quiet stretch of highway.
Off the Record, for colleagues
Off the Record is the version that is safe for work: meetings, feedback, the unwritten rules every office runs on. Uncomfortable questions to ask coworkers usually go wrong because they get personal. These stay about the job. "Which recurring meeting would I say should have been an email?" is a reliable opener on the drive to an offsite. "What would I say is the real reason projects here run late?" is where it gets interesting, and where the ground rules below matter most.
Ground rules that keep it a game
Questions like these need a few rules, said out loud before the first round. It takes ten seconds, and it is the difference between a trip people bring up for years and one they would rather forget.
- Anyone can pass. Whoever is in the hot seat can say "pass" and the round moves on, no explanation owed. A game you cannot pass in is an interrogation.
- Bold, never cruel. A guess can be cheeky. It should not be the thing you know would really hurt. If you would not say it to their face while they are laughing, keep it.
- No names at work. With Off the Record, talk about meetings and habits, never about a named colleague who is not in the car. "The Monday one" is fine. "Dave's Monday one" is not.
- The driver never touches the phone. Car Mode reads every question aloud, so the driver guesses and answers out loud like everyone else, with eyes on the road and hands on the wheel. The next question is one press of the buttons already on the steering wheel, so nobody asks the driver to look at a screen, not even for the good bits.
Who it works for
This game needs people who already know each other a bit, because there has to be something to guess from. A car full of strangers will produce a lot of wrong guesses and not much else. Start them on something lighter.
It also needs time. The first two rounds are careful. Somewhere around the fifth, people stop protecting themselves and start guessing properly, so a drive of an hour or more gives it room.
And it is not for every mood. If someone is tired, worried or has had a rough week, a deck of things we don't say is the wrong choice. Play something easy and save these for the good stretch of the drive.
Closer or enemies by the next exit
That is the honest promise of questions like these, and most of the time it comes out closer. Your oldest friend turns out to have held a tiny grudge for six years, and it is about a sandwich. Your partner turns out to have been worried about the same thing you were.
Now and then it goes quiet for a mile. That is allowed. Let whoever is in the hot seat decide when to move on, then open MileSmile, choose What Would I Say?, and find out how well your people really know you.