Jail conversation questions
A discussion worksheet with questions about prisons for older ESL students, with a picture description activity. The topic is obviously not suited to younger students and teenagers. It can also spark sensitive political conversations, which are best avoided. Just exclude the questions that are not appropriate in the country or situation you are having this conversation!
You may want to mention to your class that this handout uses the modern English spelling of jail. Although it is pretty much obsolete, they may come across the old English spelling of gaol from time to time.
Some of the words to pre-teach before doing this exercise using the free printable PDF above include – handle, imprisoned, escape, stuck, rehabilitate, jail time, treat, compensate, and riot.
The jail conversation questions –
1 – What are 5 words that you associate with jails and prisons?
2 – Do you think you could handle prison? For how long?
3 – What would you do with your time if you were imprisoned for several years?
4 – Where is the closest prison to you?
5 – Would you live next door to a jail? Why or why not?
6 – In what ways do people escape from prison?
7 – Do you know any interesting prison escape stories?
8 – What do you think would be the worst country to be stuck in jail?
9 – What is your favourite prison movie?
10- Do you know anyone who has been to jail? What for?
11- Who is the most famous criminal in your country? What did they do?
12- Do you think that jail sentences can rehabilitate people?
13- In what ways are prisons dangerous?
14- Are there any crimes that lead to jail time that you disagree with?
15- Do you think you could work in a prison? What job could you do?
16- What do you think prisoners eat in jails?
17- If you had to go to jail, how would you behave on the first day?
18- If people are wrongly imprisoned, how do you think they should be compensated?
19- Do you think women’s prisons are safer than men’s prisons?
20- For what crimes should people serve life in jail?
21- If you escaped from jail, where would you run to? How would you get there?
22- What things do you think are not allowed in prison?
23- Do you think older prisoners are treated better than younger ones in jail?
24- Why are there sometimes riots in jails? What would you do if you were in one?
25- Do you think many rich people go to jail? Are they treated differently?
26- What are some minor crimes that people go to jail for in your country?
27- Is there anyone that you think should be in prison but is not? Who and why?
28- What is the most notorious prison that you know of? Why is it so infamous?
29- How would you feel about prisoners being put to work in chaingangs as they were often in the past?
30- Do you believe that people who commit financial crimes are treated too leniently? Why or why not?
31- What changes would you like to see happen in prison systems in your country?
32- About how much time in jail are bank robbers usually sentenced to, where you live?
33- What do you think the best country to go to prison in the world is and why?
34- If you could take 3 things into a prison, what would they be and why?
35- Do you think that zoos are like prisons for animals? In what ways are they different?

Prison and jail idioms
Here are some related expressions to the jail conversation questions that may be of interest to your students.
There are a few slang terms for prisons and jails, and a jail can be referred to as the joint, the big house, the pen, or the slammer.
If a person manages to get out of a very difficult situation, it can be said that they get out of jail.
If somebody is sent to prison for committing a crime, we can say that they are behind bars, in the clink, or will do time.
A jailbird is a person who has been to jail several times or is repeatedly in and out of prison.



