One common misconception those outside the prison walls have is that prisoners are hard, tough, and do not want any form of entertainment. Well, the bias is understandable but not all true.
The fact is like you and I, most prisoners will trade a good laugh and funny question if the opportunity arises, and should you find yourself amongst them, asking funny, light-hearted questions could be the memory they need to have till their time in the penitentiary elapses.
Without delay, I have compiled a list of funny questions you could ask a convict either still serving or out of prison.
Remember that the key to these questions is asking from a place of joviality.
20 Funny and Interesting Questions to Ask a Prisoner?
Here are 20 interesting and amusing questions to ask a prisoner in no particular order:
- Have you thought of a jailbreak?
- Is there any odd food you’ve eaten while in prison?
- What would you choose to wear over a prison uniform?
- If you could go back to advise your free self, what would you say?
- Is there any weird thing someone has said while in prison?
- If you could have one luxury item in your cell, what would it be?
- What’s your favorite prison movie?
- What would you like to do if you get out of prison?
- If you could rename the prison, what would you call it?
- What ingenious way have you seen a person bring contraband into the prison cell?
- Have you engaged in a fight while in prison?
- What special talent do you have?
- How do you keep yourself busy when bored?
- What’s your favorite sport to play?
- Do you have any role models you look up to?
- What’s the silliest prank you’ve witnessed?
- What would you want to have in a prison cell given the opportunity?
- What’s the weirdest request you’ve made to a guard?
- Is it boring in prison?
- Does the warden maltreat you?
1. Have you thought of a jailbreak?
Thinking of a jailbreak isn’t a strange thought for a prisoner, partly because they need to get out of their confinement, and asking this question is an excellent and funny question to ask a prisoner.
For example:
- I bet you have thought of jailbreak before.
- Since you came here, have you ever thought of a jailbreak?
2. Is there any odd food you’ve eaten while in prison?
If you want to see the fun side of that prisoner, then asking if they have eaten any odd food while in detention will do the magic.
The question is a funny way to know the state and condition of welfare in the prison and how prisoners feel about it.
Asking this question provides the answer you need in a very humorous way.
For example:
- What would you say is the worst food you’ve eaten while in prison?
- Have you had an experience where you eat something awful right here in the prison?
3. What would you choose to wear than a prison uniform?
The question is a way to know if a prisoner is happy to wear a prison uniform or if they prefer to be allowed to choose what outfit fits them if given the opportunity.
Playfully ask to know what the prisoner thinks and wishes for.
For example:
- Will you choose to wear a prison uniform or something else?
- Do you like wearing the prison’s uniform or do you want liberty in the outfit you wear?
4. If you could advise yourself, what would you say?
Slide this question when you feel the urge to know if a prisoner is remorseful or bull-headed. Asking this question reveals the intent of a prisoner and their decision to change or not.
For example:
- I want to know my friend. If you could advise yourself, what would you say?
- Will you say that you need any advice at the moment for yourself?
5. Is there any weird thing someone has said to you while in prison?
Perhaps someone might have done or said something not right to the prisoner whom you are having a conversation with and that has led him to harbor some resentment and a plan to get back at the person who made such a statement at him, you asking this question could be the ice breaker needed to douse the tension.
Get started with these examples:
- Has anyone said something weird to you while in prison?
- What’s the weirdest thing someone has said to you while in prison?
6. If you could have one luxury item in your cell, what would that be?
What’s unique about the question is how it reflects a prisoner’s aesthetic taste and love for beauty. So, if you want to know how dandy or fashionable your prisoner friend is, then slide the question suggested above.
For example:
- You seem to be someone who loves beauty, so if you could have one luxury item in your cell, what would that be?
- Your fashion sense speaks volumes. If you could have one luxury item in your cell, what would that be?
7. What’s your favorite prison movie?
For a cinephile, this question is ideal for having a smooth conversation.
Asking them what their favorite prison movie is shows that you also share in their love for motion pictures and respect their choices.
For example:
- Do you have any favorite prison movies?
- I kind of love the movie Prison Break. How about you? What’s your favorite prison movie?
8. What would you like to do if you get out of prison?
Asking this question is a way to relate to what the prisoner would like to do outside the prison walls and also suggests occupations and skills that can make them useful to society.
For example:
- Your time is almost over. What would you like to do if you get out of prison?
- Do you have any plans for what you would like to do when you get out of prison?
9. If you could rename the prison, what would you call it?
An excellent question to ask is to know what name the prisoner would rename their prison if given the opportunity.
Getting the opinion of a prisoner is a way to make an informed judgment on the state of the prison and what needs improvement.
For example:
- What would you name this prison if you could rename it?
- Have you thought about renaming this prison cell?
10. What ingenious way have you seen a person bring contraband into the prison cell?
If you are looking to understand the ingenuity of inmates, then asking in this section is a good start.
Your prisoner friend will gladly tell you some devious and very smart ways other inmates bring in contraband if you approach the question in a less serious way, which will shape your perception of prison life and prisoners.
For example:
- I have heard rumors about how inmates smuggle contraband in some prisons. Could you share with me a similar experience?
- What ingenious ways have other prisoners succeeded in bringing contraband to the prison cell?
11. Have you engaged in a fight while in prison?
Give that prisoner the benefit of the doubt by asking if they have ever engaged in a fight while in prison. This question will give you a hint about the personality of the individual you are chatting with.
For clarity, check out this example:
- You don’t seem to be the troublesome type. Have you engaged in a fight while in prison?
- Has an inmate that you got into a fight with any of them has pissed you off?
12. What special talent do you have?
The essence of the question stated above is to know if that prisoner has any skill that, when used, will fetch them a decent income and give them a fresh start upon being released.
Asking this question opens up an avenue to have your prisoner show you their exceptional abilities overlooked by many.
For example:
- Do you have any special talent you want to tell me about?
- What would you say is your special talent?
13. How do you keep yourself busy when bored?
If you seek to know how a prisoner spends their pastime, then the question in this suggestion is ideal for a good conversation.
By seeking to know about a prisoner’s personal life, you open a door for trust and openness for them to hold a conversation with you.
For example:
- Some prisoners love chess. How do you keep yourself busy when bored?
- When you aren’t doing anything, how do you keep yourself busy?
14. What’s your favorite sport to play?
Talking about sports is another way to go in the list of questions to ask a prisoner, it gets interesting if the prisoner is a sports enthusiast.
By asking them what their favorite sport is, you connect with their passion and also let them know how non-judgmental, you care about their choices and opinions.
For example:
- You do like sports, don’t you? What‘s your favorite sport?
- If you had a sport in mind you wanted to try your hands on, which would it be?
15. Do you have any role models you look up to?
You never can tell the reason for that prisoner’s behavior if you don’t ask who they draw their inspiration from, which is why the suggestion here is ideal if you want to know.
You get a glimpse of why the prisoner acts the way they do and who they are imitating when you inquire of them who the role models they look up to are, which makes it easy to curtain or manage any underlying shenanigans.
For example:
- You have a role model, whom you look up to, don’t you?
- Is there a personality you admire so much that you would not mind imitating?
16. What’s the silliest prank you’ve ever witnessed?
Pranks can be a good way to liven a place if done right, same applies to asking a prisoner who is known for their witty and prankish nature.
The question is a funny way to get a prisoner to expose some naughty behavior of some inmate and either curtail or reprimand the culprit.
For example:
- A lot of inmates here have a way to prank others. What is the silliest prank you’ve ever witnessed?
- Is there a point where you witness a prank go wrong or you have pranked the wrong person?
17. What would you want to have in a prison cell if given the opportunity?
The essence of this question is to understand the prisoner’s need to make their cell experience comfortable while still serving their time at the correctional service.
Asking them this question makes it possible for them to speak up about what they feel will make life easy for them.
For example:
- The superintendent is paying a visit tomorrow. What would you want to have in the prison cell if given the opportunity?
- Hello Inmates, I am here to carry your request to the Department of Prison Service. What would you want to have in a prison cell if given the opportunity?
18. What’s the weirdest request you’ve made to a guard?
Out of curiosity, you can ask what their weirdest request was talking to a guard. This question is a fun way to relate and also bask in the comfort of a good joke without sounding serious.
For example:
- You are weird, let me ask; what’s the weirdest request you’ve made to a guard?
- Have you ever asked a guard for something out of place? I mean something weird?
19. Is it boring in prison?
‘Is it boring in prison’ is a question asked because you are keen to know what it feels like being locked up and restricted from accessing the things most freemen can access.
This question, when asked, requires carefulness and is said in the lightest flair possible to avoid reading the wrong meaning to it.
To get a better glimpse, here are some examples:
- It sure must be boring here I guess?
- Aside from the roll call and daily workout, isn’t there something exciting to do?
20. Does the Warden Maltreat you?
By asking, you create a safe space for the prisoner to voice out their disgust or appreciation for the wardens who either maltreat them or treat them right.
In addition, you build in their mind that someone somewhere empathizes with their plight and is desirous to know about their living condition.
For example:
- Be honest with me my friend, does the warden maltreat you?
- I’d help you in every way possible. However, I need your cooperation. Does the warden maltreat you?
To wrap up
Now you have no reason to be stuck on the questions to ask a prisoner again, as with the suggestions given in this article, you are halfway to engaging that inmate in a meaningful and friendly conversation.
Keep abreast and refresh your memory by bookmarking this page and visiting whenever you feel lost on words or questions to ask a prisoner if you come across one.