Funny Questions to Ask Prisoners
Twenty light questions for visiting someone in prison or writing to them, kept clear of the case and the sentence: the best food of the month, the funniest person on the block, the skill that would look absurd on a resume, and the first meal they want when they get out.
The questions
Open any question for the note
What's the best thing you've eaten in the last month?
Why ask it
Food is concrete and needs no explanation of their case, which is why it works as the first thing out of your mouth. Expect a very specific answer, one sandwich or one packet of noodles, rather than a category.
Who around here has the worst taste in television?
Why ask it
Complaining about someone else's viewing habits lets them describe the people near them without informing on anyone. The names that come up are usually the ones they actually spend their days with.
If you got to pick the music for everyone for one day, what goes on?
Why ask it
The list tells you which year they are anchored to. If it stops dead at the year they came in, note it and move on rather than pointing it out.
What's a skill you've picked up in here that would look ridiculous on a resume?
Why ask it
Improvised skills are a source of pride and usually come with a step-by-step explanation. A shrug instead often means they are early in a sentence and still keeping their head down.
Who's the funniest person you've met in here, and what makes them funny?
Why ask it
Asking them to explain someone else's humour gets you a much better story than asking them to be funny themselves. It also tells you whether they have found anyone they trust.
What's the most useless advice anyone has given you since you got here?
Why ask it
This invites them to mock the advice rather than the adviser, so it stays safe. It also quietly tells you which advice they did take.
What's a show or film everyone raves about that you think is overrated?
Why ask it
A contrarian opinion is one of the few things nobody can take away, so people defend theirs with real energy. This is the question that most often turns into a proper argument, in a good way.
If someone made a series about this place, which character would you be?
Why ask it
Casting themselves shows how they think they are read by others, which is rarely how they actually behave. If they pick the background extra, they are telling you they work hard at being unremarkable.
What's the pettiest argument you've watched drag on for a week?
Why ask it
Petty disputes are the safest window into daily life because nothing serious is at stake in the retelling. The detail they remember best tends to be the trigger, not the fallout.
What's the worst haircut you've ever had?
Why ask it
Everyone has one and nobody minds admitting it, so this reliably resets the mood after a heavier stretch of conversation. Bad answers are vague, so ask who cut it and why they agreed.
What's the most ridiculous rumour that's gone around about you?
Why ask it
Correcting a silly rumour gives them the pleasure of setting a record straight with no cost. Keep it on the absurd ones: if the answer turns toward their charges, change subject.
What food do people out there go on about that you honestly wouldn't miss?
Why ask it
Inverting the usual craving question stops it from becoming a list of everything they cannot have. The answers are often oddly specific and turn into a running joke between visits.
If you could add one thing to the commissary list, what would you argue for?
Why ask it
This gets you practical information about what they actually want without making them ask you for anything. Listen for the item mentioned twice, then check what the rules allow before you offer.
What's the strangest dream you've had that you still remember?
Why ask it
Dreams are shared without anyone having to claim they mean something, and the retelling is usually funnier than the dream. If the dreams are all about the outside, that is a signal to keep the rest of the visit light.
What were you completely certain about at nineteen that you find funny now?
Why ask it
This lets them laugh at an earlier version of themselves rather than defend the current one. The answers are usually about money, women, or how tough they were, and they know it.
What's the worst job you ever had on the outside?
Why ask it
Bad-job stories are a subject where their life sounds like everyone else's, which is often a relief. The complaints tell you what kind of work they could actually stand doing again.
If you had to teach a class in here on anything at all, what would you teach?
Why ask it
Being cast as the one who knows something is a rare position, and most people take it seriously even when they answer with a joke. The subject they pick is often what they would like to do with the years ahead.
What's a story about yourself you've told so often you've stopped trusting the details?
Why ask it
This admits that memory drifts without accusing them of lying, so it usually gets an honest answer. Expect the version you get to be the polished one, and expect them to say so.
What's the first meal you want when you're out, and who's cooking it?
Why ask it
The cook matters more than the food here: the name they give you is the person they most expect to still be there. If they dodge the second half of the question, do not press it.
What would you rather people laughed at you about than felt sorry for you about?
Why ask it
This is the one question that names the thing everyone in the room is managing, and it gives them the say in it. Answers are short and worth taking as instructions for the rest of your visits.
Keeping a visit light without making it hollow
Practical guidance for the conversation itself
Before you ask anything
Assume you are overheard
Visits and calls are usually monitored and recorded. Anything that touches their case, an appeal, or anyone else's conduct can cause them real trouble, so keep every question on the side of daily life and the past.
Let them set the register
Some people want an hour of nothing serious. Others will steer straight into what is hard and then want to come back out again. Follow the turn each time rather than deciding in advance which kind of visit this is.
Do not promise anything
A funny conversation puts you both in a generous mood, which is when people offer money, visits, or phone calls they later cannot deliver. Say what you can do next week, not what you can do in general.
Where the humour actually comes from
Almost none of it comes from jokes. It comes from specifics: the exact petty argument, the exact commissary item, the exact bad haircut. When an answer arrives as a generality, ask for the name, the day, or the amount, and the story appears. If you supply the punchline yourself, you have taken the only thing they were contributing.
What to keep off the list
Anything that fishes for prison stories
Questions about violence, contraband, or who runs what are entertainment for you and risk for them. If they choose to tell you something like that, listen and do not ask a follow-up.
Release dates as a punchline
Counting down is fine if they raise it. Turning it into a joke, or asking what they will do with all that free time, lands badly and is hard to walk back.
Questions that require them to have news
Most weeks nothing has happened. Asking what is new produces an apology. Ask about a specific person, meal, or argument you already know about instead.