What to Talk About With Someone in Jail and Prison

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The famed Russian novelist and Soviet critic Aleksandr Solzhenitsyn recalled in his book, The Gulag Archipelago: 1918-1956, Volume 2, that his years in prison benefitted his life.

In fact, one of Solzhenitsyn’s famous lines from the book is “Bless you, prison!” which astonished most of his readers. 

However, if you are talking with an incarcerated person or someone who has experienced incarceration, describing their situation as a blessing is probably the last thing that you should do.

Generally, incarcerated individuals have more significant physical and mental health needs than ordinary citizens. 

A 2018 BMC (BioMed Central) International Health and Human Rights study suggests that specific language can help improve inmates’ health and well-being.

Words matter when interacting with people in jails or prisons. Therefore, you may ask: 

What do you talk about with someone in jail? What attitude should you have when talking about someone in jail? What are some ways you can make an inmate feel special?

You may also wonder about how you can contact inmates and what questions you can ask in incarceration facilities.

lookupinmate.org is an all-in-one site where you can access information about inmates and correctional facilities nationwide. Read on to know more about topics you can discuss with someone in jail or prison.

What Do You Discuss When Visiting Someone in Prison?

Below are topics you can use when beginning a conversation with an incarcerated loved one or a family member.

Share Your Joys

One of the best ways to help inmates feel better is to share your positive experiences from the outside world with them. 

Inmates’ day-to-day life can be incredibly dull and uneventful. Their daily routine typically includes labor, community service, and other rehabilitative activities.

Therefore, you can spread a little joy in your loved one’s life by sharing how you overcame a tough time. Telling them what makes you happy can help brighten their day. 

Share Your Troubles

Sharing your troubles with an inmate can help make them feel someone still needs and value them. 

Sometimes, incarcerated individuals have difficulty imagining a world beyond their cells or the correctional facility’s compound. This limitation can make them feel like they are the only people experiencing the worst hardships in life. 

Visitors can share bittersweet memories with their loved ones or show them pictures of family members. One of the best presents to give people in jail or prison is a sense of normalcy despite their situation.

Let Them Know They Are Loved

Inmates may feel like nobody wants them anymore because of the shameful acts they committed. 

One way to help them navigate through their lack of self-worth is to show them you love them.

Gary Chapman, a counselor, and author of the best-selling book The Five Love Languages, listed five ways people can feel loved. These expressions of love are:

  • Words of affirmation
  • Acts of service
  • Receiving gifts
  • Quality time
  • Physical touch

For example, some inmates may feel loved if they receive undivided attention from their loved ones. Visiting them on special occasions, such as birthdays, is a way to show your incarcerated friend or relative that you love them.

You can also send gifts to a loved one in jail or prison as a token of your love for them. You can buy them things like commissary products, including snacks or hygiene items.

Lend a Listening Ear

Sharing your joys and troubles in life may help inmates get through their days in prison. However, listening to their stories is equally important.

The most common way inmates communicate with people outside the facility is by making collect calls.

A person in prison or jail may not have an outlet for sharing personal feelings, thoughts, and experiences. Listening to inmates can help them process their experiences and think of ways they can improve their lives.

Be Wary of Future Planning

Planning for the future can be a touchy subject for many inmates. Release dates are often uncertain, making it difficult for prisoners to discuss their plans.

Therefore, you should focus your conversation on fun moments, memories, and joyful times together. 

Talk About the Prisoner’s Families

If the inmate is a friend or someone you have met through an outreach program, show concern for their families.

Asking inmates about their children can help brighten their days. Sometimes, people in prisons or jails may also enjoy listening to light-hearted stories about children. 

However, be careful not to share too much personal family information. 

Moreover, do not exaggerate stories of happy family memories. Inmates are painfully aware that they are missing out on their own families.

Encourage Forgiveness

You can also help inmates view life from another perspective by sharing with them stories of forgiveness. 

Telling incarcerated individuals how you have forgiven someone can also help them let go of their emotional baggage, reconnect with loved ones, and make amends.

Do Not Be Scared of Emotions

Talking about and working through emotions is essential when talking with a loved one in jail. However, it can be difficult for them as they may be experiencing intense sadness and pain. 

Nevertheless, discussing how they are feeling and maybe crying together can be good to go through at the start of your visits so you can end your time with positive things.

Talking With Prisoners

No Topic Is Off Limits During a Prison Visit

You can talk about any topic you want with people in jail or prison, as long as these topics do not encourage criminal behavior. Corrections facilities usually have assigned officers who monitor any form of conversation in jail or prison, including inmate calls.

Your conversation with an inmate depends on your relationship with them or the reason for your visit. 

However, it is vital to maintain calmness and pleasantness during your talk so that everyone can leave the visit feeling good about the experience.

You can talk about the weather or the food you made for dinner last night. Your conversations vary depending on whom you are visiting. 

Where you fit into the inmate’s life determines where the discussion goes.

Visits Are Important to Prison Inmates

Visits are essential for the overall well-being of inmates and their loved ones. These events help maintain a sense of connection and normalcy between individuals who care about each other. 

Additionally, visits keep everyone updated regarding what is happening in each other’s lives. 

Questions to Ask a Prison Inmate

 Here are some questions you can ask a prison or jail inmate to stimulate an engaging conversation.

What Is It Like to Be in Confinement?

Every incarcerated individual has a unique take on what it means to be in prison. However, a common denominator among these people is that they dislike incarceration.

Incarceration is nothing like real life. Due to the nature of their jobs, correctional officers tend to be overly strict or aggressive. Therefore, many inmates continue to dream of being free from the facility.

Getting the inmate’s unique perspective of what incarceration means to them can help you appreciate and understand the benefits of living in the free world.

What Is the First Thing You Must Do After Release?

Most inmates have a comprehensive list of things they want to do after release, assuming everything goes as planned. These people are willing to answer questions about their plans once they are released without having negative emotional sentiments.

Most correctional institutions allow inmates to learn skills and get a degree. These initiatives make it easier for offenders to reintegrate into society.

Still, even if many want to talk about their plans to become self-sufficient after imprisonment, they are not always the case. 

Some inmates do not have extensive plans and only want to see their family and friends after release.

How Has Prison Changed You?

Most inmates will have a new opinion of the world during and after their imprisonment. They do not usually stay as they were before their jail or prison sentence and have a new outlook on life.

Moreover, inmates significantly appreciate what it means to be free, including being free to leave their place or eat the food they want. 

Other offenders are also determined to make something good out of their lives after serving their sentences by enrolling to get a degree or a skill.

What Was Your Favorite Prison Food?

Asking someone about their favorite food is a normal part of the conversation between friends. As such, it is not problematic to ask the same question to an inmate. 

Contrary to popular opinion, inmates do not always eat bad food during their stay in prison. For the most part, the food is manageable. 

However, unlike you, inmates do not have the freedom to eat any food they like. While they have a preferred meal among the many foods served in facilities, they may only be able to eat it once in a given month.

Did You Have Friends Amongst the Prisoners? What About the Guards?

It is natural for inmates to form bonds with their fellow prisoners because correctional facilities still resemble the outside world. 

When incarcerated individuals have something in common, they can become friends and interact well. For example, people of a specific ethnicity can get along quicker and better than others.

While inmates form good bonds amongst themselves, bonding with the prison guards is different. 

Other prisoners view inmates who are friends with the correctional officers as traitors, exposing the secrets of their daily lives. 

Did You Meet Any Prison Bullies?

Most institutions have prison bullies, who act as the prison version of school bullies.

There are not many violently dangerous inmates. However, bullies are still present in jails or prisons.

Additionally, because correctional officers are often less amiable than the bullies, it is not a viable alternative to report a bully to them.

Fighting the bullies off is the only way to get rid of them. After a fight, most inmates stay in solitary confinement. Therefore, prisoners generally refrain from fighting.

What Is Your Advice to Young Criminals?

If given a second opportunity, most inmates would not choose to commit the crimes they have perpetrated.

Individuals who have been in incarceration facilities before can be the best individuals to advise young people who are treading the wrong path.

You can ask questions to gather knowledge about prisoners and prison life.

How Did You Get Into Prison?

Depending on whom you are talking to, the question can cause a lot of emotion. If the prisoner appears very reserved, you may want to refrain from asking this question.

You may have many guesses regarding events leading to people’s incarceration. However, most of the actual reasons for their imprisonment are not what you might expect. 

For example, some people are serving crimes they cannot recall committing and for which they have received an unexpected criminal sentence.

What Is the Scariest Thing You Have Experienced In Prison Recently?

Prisons are usually full of terrifying stories, some of which are unexpected.

Some people may have experienced solitary confinement due to participating in a fight or for no legitimate reason at all. Others feel scared if they hear about the various diseases that occur in prison virtually every day.

You should strive to gain an understanding of the inmate’s particular perspective on the dangers of prison life when talking with them.

How Long Do You Get Locked Up in a Cell?

Inmates do not spend their entire lives confined to a cell. They also connect and participate in group activities to improve their mental health.

You can inquire about the prisoner’s sentence duration if you are interested. Inmates who work typically spend up to 10 hours a day outside of their cells, and those who do not, usually enjoy up to eight hours of free time.

That set-up is subject to state prison regulations, though inmates’ situations can differ. You should check with officers to be sure by asking this question.

Do You Think Jail Serves Any Good Purpose?

You may not get the response you are hoping for when you ask prisoners about the purpose of incarceration.

While you may think that most inmates agree that jails or prisons reduce crime and help convicted individuals reenter society, you are mistaken.

For example, most inmates believe their imprisonment is unfair. They believe that the criminal justice system can be severely prejudiced.

Most prisoners harbor resentment toward the prison system, even though some enjoy rehabilitation programs that try to reintegrate convicts into society.

What Do You Talk About With a Significant Other During a Prison Visit?

You must be open and honest about your positive or negative emotions if your significant other is in prison or jail. Sharing your hopes for the future of your partnership is another smart move.

Be honest about your feelings and let your spouse know whether you are hurting or afraid. Any relationship can benefit significantly from the time spent apart when their partner is in incarceration. 

Additionally, it can be a secure moment to end toxic and abusive relationships.

What Do You Say to Your Boyfriend or Girlfriend in Jail or Prison?

The same things you would say to your girlfriend or boyfriend if they were not in prison. The four walls are limiting enough; do not let prison define your conversation with your significant other. 

Although it may help to be more encouraging than nagging, your partner still wants to know about your good and bad days as usual.

Writing Love Letters to Prison Inmates—What to Say

It takes a lot of bravery to put your thoughts on paper. You can always start small if you doubt your ability to express your feelings in words. 

Here are some suggestions for topics to cover in your letters of love:

  • Discuss your daily activities.
  • Inquire about their day.
  • Encourage your partner to persevere and to have patience.
  • Include motivational sayings or write honestly.
  • Talk about a book, movie, or TV show.
  • Make them laugh with a funny story or a joke.

What Do You Talk About With Kids During a Prison Visit?

The lives of many imprisoned parents are frequently tricky. Inmates miss so much of their children’s lives and are hungry for information about their children’s daily routines. 

They want their children to draw a picture, sing a song, give them lots of hugs, and simply be themselves.

What Can You Say to Encourage Someone in Jail?

You can offer kind words to inmates to encourage their positive behavior. 

These reassuring words can include complimenting their progress, telling them you are praying for them, or giving them hopeful thoughts regarding their situation. 

How to Discuss With an Inmate

You may have to be especially sensitive when speaking with an inmate. Here are a few characteristics that make engaging with them more manageable.

Team Up

If you are a volunteer visiting a prison to help inmates, working in a group is preferable to working alone. 

Although each volunteer has a unique set of skills, you can work as a team to accomplish more tasks. 

Acknowledge Human Dignity

Think of inmates as regular men and women, the sons and daughters of someone, or people who are married with families of their own. You should think of what they could be rather than what they are right now.


Being in prison makes it easier to form negative thoughts, from the scary tales of how people ended up in jail to the more terrifying prison riots.

Let the prisoners know you care about them and that they are not alone. This certainty can nudge them toward honesty and openness with you.


You may have more difficulty talking with an inmate if you are not naturally good at making friends.

Prisoners are accustomed to daily encounters with unpleasant people. Frustrated inmates typically hesitate to share anything with people whose outlook is similar to theirs.

You should give inmates a warm smile when talking with them. The conversation may turn contentious, so try to be compassionate and empathic.

Be Genuine

You can discuss your daily challenges openly. Do not portray yourself as the ideal person, and just be honest. Inmates can tell when individuals are acting like someone they are not.


Prisoners frequently believe that society views them as inferior, and they can be partially correct in this belief. 

Most people view law offenders as moral failures, so they do not respect them.

Given that prisoners are rarely treated with respect, either by their fellow inmates or by society at large, demonstrating some respect can significantly boost your chances of relating to them.

Be Yourself

Do the best you can with the best you have for inmates. Avoid exaggerating what you can do for them.

 You can give a lesson or deliver an encouraging talk. However, you can still significantly impact prisoners by engaging in conversation, lending an understanding, and demonstrating compassion.

How Do I Make an Inmate Feel Special?

Keep Them Entertained

The prison’s gloomy, somber atmosphere punctuated by silent moments can feel very restricting for inmates. 

Life in prison can be repetitive and depressing. You can improve their days, if only for a little while, by having interesting or entertaining conversations with them.

Make Them Feel Important

Confinement can feel oppressive for many inmates, especially if they live in a small, dirty cell with other prisoners. 

Making people feel valued and needed is one of the most acceptable methods to lift their spirits.

Send Some Gifts

You can send gifts to encourage someone in jail or prison. Inmates usually appreciate even the littlest things coming from their loved ones. 

Send Items

Here are items you can send an incarcerated individual:

  • Care packages
  • Paperback books
  • Postcards and greeting cards
  • Magazine and newspaper snippets

Send Them Money

Your incarcerated loved one may not have access to phone cards, stamps, or envelopes without money, which are essential for keeping in contact.

Money is also helpful for buying necessities and upscale alternatives, such as clean clothing, toothpaste, toiletries, and good meals.

Visit Them at the Prison

All of us require face-to-face communication, but your loved ones in jail may not receive it as frequently as they would like.

Although it can be hard for you to visit the correctional facility, your friend or family member will sincerely appreciate your efforts in visiting them. 

Ensure that you are not wearing jewelry, loose clothing, or anything else that looks like a weapon before entering prison. 

Continue to Stay in Touch

Visiting a loved one in prison is incredibly important. However, it is also crucial to maintain contact in-between visits. 

The inmate can benefit much from maintaining contact and being reminded that they are loved and valued.

Send Them a Letter

One of the most effective ways to contact your loved ones is by writing a letter to them, especially if you are not on their contact list or cannot afford to make a collect call

Speak on the Phone

Your loved one can call you after they add you to their contact list. Schedule a time when you are both available because you cannot contact your loved one back if you miss their call. 

Inmates are also responsible for paying the collect fees if your call returns to voicemail.

What to Avoid

Avoid specific topics like death in the family or personal struggles that the incarcerated individual is facing that you cannot help them solve.

The inmate may already feel helpless and disconnected from their loved ones and do not need the additional pressure of the person on the outside’s struggles.

Phone Call From Jail or Prison? Better Watch What You Say

Generally, correctional facilities are not allowed to record private conversations between lawyers and clients. 

However, there are still incidents of taped calls happening in some institutions. Therefore, if you are talking with someone in jail or prison, you should be careful about what you say to them. 


  1. What do you say to a guy in jail?

An individual in jail or prison usually wants to know what is happening in the outside world. 

Inmates may want to catch up on your life if you discuss good grades in class, work promotions, engagements, or marriages.

  1. Do relationships with inmates work?

No matter who is involved, relationships are complex. Still, the likelihood of a relationship succeeding may be less if your partner is in jail or prison.


1. Aleksandr Solzhenitsyn: “Bless You, Prison!”
2. Words matter: a call for humanizing and respectful language to describe people who experience incarceration
3. Understanding the Five Love Languages

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