Navigating conversations with someone who’s been to prison can be tricky, especially if you want to build trust and avoid causing discomfort. Many people don’t realize that certain questions can reopen old wounds, reinforce stigma, or even impact someone’s ability to reintegrate into society. With over 600,000 people released from state and federal prisons each year in the U.S., chances are you’ll encounter someone with this experience—whether at work, in your community, or even within your family. Understanding what not to ask is crucial for fostering respect and supporting successful reentry. This guide will help you avoid common pitfalls and make more informed, compassionate choices in your interactions.
1. What Did You Do?
Asking directly about the crime is one of the most invasive questions you can pose. For many, their conviction is a deeply personal matter and reliving it can trigger shame or anxiety. The U.S. Department of Justice reports that nearly 1 in 3 Americans has a criminal record, but not all convictions reflect the person’s character or current life. Instead of focusing on the past, prioritize the present and future. If someone wants to share their story, let them do so on their own terms.
2. Were You Scared in Prison?
This question can trivialize the trauma many people experience behind bars. Research from the Prison Policy Initiative highlights that incarcerated individuals face high rates of violence, with over 200,000 assaults reported annually in U.S. prisons. Asking about fear can force someone to relive traumatic events and may make them feel unsafe or judged. Instead, offer support by listening without probing for sensational details.
3. Did You Meet Any Famous Criminals?
Curiosity about notorious inmates might seem harmless, but it reduces a person’s experience to entertainment. This approach ignores the real challenges of incarceration, such as isolation, loss of autonomy, and the struggle to maintain relationships. Focusing on celebrity criminals can make someone feel like their pain is being minimized or turned into a spectacle. Keep the conversation centered on the individual, not sensational stories.
4. How Long Were You In For?
While this might seem like a neutral question, it often leads to judgment or assumptions about the severity of someone’s crime. Sentencing disparities are well-documented, with people of color receiving longer sentences for similar offenses compared to their white counterparts, as shown by the Sentencing Project. Instead of asking about the length of time served, focus on the person’s current goals and achievements.
5. Are You Allowed to Vote or Get a Job?
Questions about legal restrictions can be a painful reminder of the barriers faced after release. Over 4.6 million Americans are disenfranchised due to felony convictions, and unemployment rates for formerly incarcerated people are five times higher than the general population. Rather than highlighting these obstacles, offer encouragement and ask how you can support their ambitions.
6. Do You Regret What You Did?
This question assumes guilt and can come across as judgmental. Many people have already gone through extensive rehabilitation and self-reflection. The focus should be on growth and positive change, not forcing someone to justify or relive their past. If you’re interested in their journey, ask about what they’ve learned or how they’ve changed, but only if they’re comfortable sharing.
7. Are You Still Friends With People From Prison?
Friendships formed in prison are often based on survival and mutual support. Asking about these relationships can feel intrusive and may bring up complicated emotions. Maintaining contact after release can be difficult due to parole restrictions or the desire to move forward. Respect their privacy and let them decide what to share about their social connections.
8. Did You Deserve Your Sentence?
This question puts someone on the defensive and can reopen feelings of injustice or resentment. The criminal justice system is far from perfect, with wrongful convictions and sentencing disparities affecting thousands each year. Instead of questioning the fairness of their sentence, focus on how they’re rebuilding their life and what support they need.
9. What Was the Worst Thing That Happened to You Inside?
Probing for traumatic stories can be deeply harmful. Studies show that over half of incarcerated people have experienced serious psychological distress, and many develop PTSD as a result of their time inside. Instead of seeking out painful details, offer empathy and a willingness to listen if they choose to open up.
10. Are You Going Back?
This question reinforces negative stereotypes and can undermine someone’s confidence in their ability to succeed after release. Recidivism rates are often cited—about 44% of released prisoners are rearrested within the first year—but these numbers don’t reflect the full picture. Many people work hard to rebuild their lives, find stable employment, and reconnect with family. Show your support by expressing belief in their potential and celebrating their progress.
Building Respectful Connections After Prison
Conversations with someone who’s been to prison should be rooted in empathy, not curiosity or judgment. The primary keyword, “someone who’s been to prison,” is central to understanding the real challenges faced during reentry. By avoiding intrusive questions and focusing on support, you help break down stigma and create opportunities for genuine connection. Remember, everyone deserves a chance to move forward without being defined by their past. If you’re unsure what to say, simply listen and let the person guide the conversation. How can you help create a more welcoming environment for someone who’s been to prison in your community?
Read More
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