When visiting someone in jail, you quickly realize that making them laugh isn’t always easy. Meeting a loved one there can feel heavy, but you can brighten the mood by sharing jokes that hit the right spot.
Cheering someone up in such a stressful place can help keep them motivated and hopeful about reuniting with you.
In this article, you’ll find over 200 funny and uplifting things to say to someone in jail to make them smile.
Key Takeaways
- The best funny thing to say to someone in jail depends on the context and your relationship with the inmate.
- You can say, “At least you don’t have to worry about what to wear everyday.”
- If you’re sending a letter, it’s better to share a short joke than simply say a funny thing.
- It makes sense to infuse encouraging words into your jokes. So after the laugh, end the joke with phrases like “Keep your head up” or “I’m thinking of you.”
A prisoner can’t see beyond the bars, so it’s up to you to keep their spirits up and help them feel alive.
When you’re telling them something funny, you’d want to say it in a way that makes them feel they are still part of your everyday life at home.
Funny Things to Say to Someone in Jail
When you’re saying something funny, it’s better to joke about the positives.
In some cases, these lines are a great way to break the ice and connect with the person, not necessarily make them laugh out loud.
The best jokes to say are ones that, in addition to being funny, make them see that you’re thinking of them and trying to bring a little bit of joy to their day.
Here are some of the best funny things you can consider saying:
- At least you don’t have to worry about what to wear every day!
- So, how’s the room service?
- Good news—you never have to pay for a gym membership again!
- Just think, no door-to-door salesmen can bother you here.
- Bet you’re becoming a real pro at making ramen by now.
- You’re basically in a 24/7, no-spending challenge.
- Don’t worry, I’ll save you some of my mom’s cooking… not that you’ll miss it.
- At least you don’t have to worry about traffic anymore.
- So, what’s the WiFi password in here?
- So how many prison push-ups do you do?
- I hear orange is the new black.
- You’ve always wanted more time to read—well, now you’ve got plenty.
- Think of it as a very, very extended vacation.
- Just remember, three meals a day—no cooking required.
- Don’t worry, you’ll be the Monopoly champ when you get out.
- I heard they’re making a reality show about prison life. You might be the next star.
- On the bright side, you’re saving a ton on rent.
- The good thing about prison? You can nap without anyone judging you.
- I know a great escape plan—just be so boring they want you to leave.
- At least you don’t have to listen to your neighbor’s loud music anymore.
- So, are you the mayor of the cell block yet?
- Just think, no need to worry about folding laundry. It’s all jumpsuits now!
- You must be the most popular person in there. You’ve always been great at making friends.
- Do you think you’ll come out as a professional chess player after this?
- Look at you, getting all that peace and quiet. I’m almost jealous.
- Are you the warden’s favorite yet? You’ve got that charm.
- This must be the longest camping trip you’ve ever been on.
- No need for an alarm clock—your new roommates have got that covered.
- I bet you’re the most organized you’ve ever been. Everything has its place in a cell.
- Think of this as a detox retreat—minus the spa treatments.
- From what I’ve seen since I came in here, who needs Netflix? You’ve got live drama right there.
- You always wanted to learn how to make new friends. Now’s your chance.
- I hope you’re brushing up on your karaoke skills for when you get out.
- Don’t worry, I’m sure they’ll let you redecorate soon.
- If you stay any longer, you will be running this place!
- What do you call a group of prisoners playing music? A jail band.
- Why did the prisoner break his watch? He wanted to serve time.
- What do you call a prisoner who takes his own photo? A cellfie.
- How do you make a prisoner laugh? Lock him in with a mime.
- Why do prisoners work out all the time? So they can lift their sentence.
- What do you call a prisoner digging a tunnel to escape? A tunnel master.
- How do prisoners talk to each other? With cell phones.
- What’s the difference between a prisoner and a job seeker? One’s trying to get out, the other’s trying to get in.
- Why wouldn’t the prisoner eat his food? He’s already serving life.
- What’s a prisoner’s favorite day of the week? Release day.
- Why did the prisoner bring a ladder to his cell? He wanted to reach new heights.
- What do you call a prisoner who’s always ready to fight? A cell warrior.
- How do prisoners talk to each other? Using cell phones.
- What’s a prisoner’s favorite day? Release day.
- What do you call a prisoner who’s always ready to fight? A cell brawler.
Short Jokes to Say to Someone in Jail
Many people believe that prisoners are always tough and don’t enjoy any kind of fun. While this belief is understandable, it’s not entirely true.
The jokes mentioned earlier might not work as well in a letter compared to when you visit the person in person.
Instead, if you’re writing a letter, you can still show your love and care by sharing something funny or joyful. You can remind them of happy memories from the past to make them smile.
Here are some of the best options:
- Prisoners always share their stories in cell blocks.
- Why don’t prisoners wear hats? They’re afraid of being framed.
- Why did the prisoner write a poem? He had a lot of verses.
- What’s a prisoner’s least favorite room? Solitary confinement.
- What do you call a prisoner taking a nap? A snore on tour.
- Prison walls are never built to scale.
- Why did the prisoner fail art class? He couldn’t draw a straight line.
- Prison math: One bar + one bar = behind bars.
- What’s a prisoner’s favorite TV show? Locked Up.
- Why did the inmate become a barber? He wanted to make the cut.
- What’s a prisoner’s favorite hobby? Collecting stamps.
- Why did the prisoner love puzzles? They kept him in pieces.
- Why do prisoners like books? They’ve got plenty of time to kill.
- Why don’t prisoners need calendars? They’re already counting the days.
- Prison life is hard, but it’s really tough on the wallet.
- Why did the inmate start a garden? He wanted to grow his own prison greens.
- Every meal in prison is a behind-bars special.
- Why did the prisoner become an artist? He had plenty of drawing time.
- Prisoners play a lot of cards. It’s all about doing time.
- Why did the prisoner take a shower? He wanted a clean break.
- Why did the prisoner make a phone call? He wanted to reach out.
- Why don’t prisoners tell secrets? Loose lips sink ships.
- Why did the prisoner start a blog? To share his cell-tales.
- What’s a prisoner’s favorite exercise? The jailhouse rock.
- Why don’t prisoners drink tea? It’s hard to stir.
- Prison food is so bad, even the rats go on a diet.
- Why did the inmate write a book? He had a lot of sentences.
- I bet you could make a mean grilled cheese with an iron by now.
- So, are you planning to open a hotel when you get out? You’ve got the hospitality experience.
- I hear you’ve got plenty of time for arts and crafts—what’s your latest masterpiece?
- At least you never have to fight over the TV remote anymore!
- So, who’s your cellmate? Do they snore as loud as me?
- Have you started writing your prison memoir yet? I expect a bestseller.
- At least you won’t have to deal with any surprise family visits.
- Well, you’ve always wanted more time to meditate, right?”
- Think of it this way—you’re living in a gated community.
- What’s a prisoner’s favorite punctuation mark? The period.
- Why did the inmate keep running? He wanted to break free.
- Prisoners always know the drill.
- Why did the inmate become a musician? He had a lot of notes.
- Why don’t prisoners trust each other? Too many jailhouse snitches.
- Why did the inmate become a baker? He kneaded the dough.
- Why don’t prisoners use the internet? They can’t break the firewall.
- Why did the prisoner love puns? They were criminally funny.
- What’s a prisoner’s favorite game? Jailbreak.
- If you learn to break out, Hollywood might call you for a movie role
- Don’t get too comfortable in there, or they might make you the warden.
- Why did the prisoner break his watch? He wanted to serve time.
- What do you call a prisoner who takes his own photo? A cellfie.
- How do you make a prisoner laugh? Lock him in with a mime.
Quick Tip:
- Jokes about prisoners can come across as hurtful, even if they weren’t meant to offend. Be sure of how your joke will affect the person before sharing it.
Lively, Encouraging Words to Tell Someone in Jail
When talking to someone in jail, it’s great to use humor to make things feel lighter, but you should also show support and understanding.
You can start by asking how they’re doing and listen to them without judging. After sharing a joke, add some kind words to encourage them.
The main thing is to let them know you care about them and that their situation doesn’t define who they are.
Here are some ideas of things you can say:
- Keep your head up.
- I’m thinking of you.
- You’re in my heart.
- We’ll get through this together.
- You’re not forgotten.
- Don’t lose hope.
- You can come back stronger.
- I’m proud of your resilience.
- You’re tougher than you think.
- Stay determined.
- Keep your faith.
- You’re in my thoughts.
- I’ll be here when you’re out.
- Use this time to reflect.
- We’re all waiting for you.
- You’re not alone.
- Take things one day at a time.
- I believe in your strength.
- We’re all cheering you on.
- Focus on the positives.
- Stay strong; you’ll get through this.
- I’m here for you, no matter what.
- Your situation doesn’t define you.
- We’re all here for you.
- You’re stronger than this.
- I’m just a letter away.
- Keep your spirit high.
- We miss you here.
- I’ll visit you soon.
- You’ve got this.
- Hold on to your dreams.
- Stay resilient.
- We’ll overcome this.
- You’re not defined by this.
- I’m with you all the way.
- You’re in my prayers.
- Stay positive.
- Keep pushing forward.
- Stay focused on your future.
- Remember your worth.
Final Thoughts
Living in prison is really hard because the constant loneliness and lack of human contact can lead to anxiety and deep sadness.
To help lift their spirits, you should try to bring some joy into their life and talk about things that make them smile—no matter how silly.
In addition to the jokes we’ve recommended, you can also share updates about what you’re watching, chatting about friends, and so on.
Sometimes, romantic or funny comments can brighten their day and connect them to life outside.
We hope you found this post helpful.
