Staying connected with someone in jail can make a huge difference in their mental and emotional well being. Whether a small gesture or a heartfelt letter, sending something fun can brighten their day and let them know they’re not alone. But what can you send an inmate?
Here are some creative and thoughtful ideas to keep your loved one’s spirits high.
9 Fun Things to Send People To Jail

1. Letters and Postcards
Never underestimate the power of a personal message as nothing can beat its charm.
A support letter to a friend in jail is enough to remind them that they are cared for and missed.
But a simple letter can be a bit boring, right? Don’t worry, You can also get creative with prison letter ideas, such as including jokes, riddles or fun facts. Postcards for inmates are another great way to send a quick, uplifting message with a beautiful picture.
2. Books and Magazines
Reading is a great way for inmates to pass the time and stay engaged. So, it’s best if you consider sending the best inspirational books for inmates to keep them motivated.
Many prisoners allow magazines as well, so sending a subscription to their favorite topic, whether it’s fitness, history or cars, can be a fun surprise.
Best Inspirational Books For Inmates:
- Surviving the Stress: A Gift for a Loved One in Jail or Prison
- Beyond the Bars Vol. 1
- From Inmate to Boss
- Chicken Soup for the Prisoner’s Soul
- The Millionaire Prisoner: Success Secrets
3. Fun and Creative Letters
Try to make your letters more entertaining by trying creative jail letters that include word puzzles, brain teasers or even short stories.
Funny things to write to someone in jail, like jokes or amusing anecdotes, can bring a smile to their face.
Here’s an example of a creative jail letter with humor and fun elements:
Hey [Inmate’s Name],
I hope this letter finds you well (and not too bored). Since I know time moves a little differently in there, I figured I’d send you a challenge to keep your mind sharp. So, here’s a brain teaser for you:
Riddle:
I speak without a mouth and hear without ears. I have nobody, but I come alive with the wind. What am I? (Answer at the end—no cheating!)
Now, for some laughs—did you hear about the guy who stole a calendar?
He got 12 months! (I know, I know, my jokes are criminally bad.)
Speaking of disasters, let me tell you about my latest attempt at being a responsible adult. I thought I’d finally try cooking something fancy instead of my usual microwave meals. Long story short, the smoke alarm and I had a very dramatic moment together. My attempt at “pan seared chicken” turned into “pan charred regret.” Even my neighbor’s cat, who somehow sneaks into my yard every day, looked at me like I had officially lost all credibility.
Keep your head up, and I’ll keep the letters coming. Looking forward to hearing from you soon!
P.S. The answer to the riddle is… an echo!
Take care,
[Your Name]
4. Care Packages and Inmate Gift Baskets
Many prisons allow inmates to receive a prison care package filled with approved items like snacks, hygiene products, and stationery. You can also send inmate gift baskets with a mix of fun and practical items. Be sure to check the prison’s guidelines on what’s allowed before sending anything.
Before sending a care package or inmate gift basket, always check the facility’s rules. Here’s a general checklist of approved items:
- Letters & Photos – Uplifting messages, family pictures (no Polaroids)
- Stationery – Notebooks, envelopes, stamped postcards for inmates
- Books & Magazines – Must be sent directly from a retailer
- Hygiene Products – Soap, shampoo, toothpaste (facility approved)
- Snacks & Instant Coffee – Sealed, non perishable items
- Puzzle Books – Crossword puzzles, Sudoku, and brain teasers
- Art Supplies – Sketch pads, coloring books, approved pencils
- Commissary Funds – If physical gifts aren’t allowed
5. Art and Activity Supplies
If your loved one enjoys being creative, consider sending them materials like coloring books, sketchpads, or crossword puzzles. Fun things to send people in jail can include Sudoku books, origami paper, or even joke books to keep them entertained.
Here’s a quick checklist of fun things to send people in jail (if allowed by the facility):
- Coloring Books – Mandala, nature, or motivational designs
- Sketchpads – Plain paper for drawing and doodling
- Crossword & Sudoku Books – Great for mental stimulation
- Origami Paper – Small, colorful sheets for creative folding
- Joke Books – Lighthearted humor to keep them entertained
- Word Search & Puzzle Books – A fun way to pass the time
- Approved Pens & Pencils – Check facility restrictions
- Short Story or Poetry Books – Encourages creative thinking
6. Personalized Photos and Drawings
Photos of family, friends or pets can mean the world to someone in jail. Some facilities even allow printed out memes or cartoons for a bit of humor. If you have kids, letting them create drawings or handwritten notes is a special and heartfelt touch.
7. Commissary Funds for Special Treats
If the facility doesn’t allow physical gifts, you can always send money to their commissary account. This allows them to buy things they enjoy, such as snacks, toiletries or even art supplies. It’s a simple way to show support and give them a bit of control over their environment.
8. Holiday and Birthday Surprises
Special occasions can feel lonely in jail, so make them extra meaningful. Send themed cards, create a prisoner gift set, or arrange for a gift for inmates that aligns with the season, like holiday greeting cards or a small birthday package.
9. Brain Boosting Games
Games can be a great way to pass the time and keep the mind sharp. While physical board games may not be allowed, there are other creative options.
There are prison letter ideas that include handwritten tic-tac-toe, word searches or even a chess game played through letters (write the board and move in each letter). Some facilities may also allow puzzle books or playing cards from approved vendors.
This small gesture can make a big difference in keeping their mind active and spirits high. Always check the facility rules before sending!
Conclusion
There are plenty of creative things to send an inmates to remind them they are loved and not forgotten. Whether it’s a heartfelt letter, a fun activity, or a thoughtful package, these small gestures can bring a little joy to their daily routine. Always check the facility’s rules to make sure your gifts comply, and keep the connection strong with your incarcerated loved one.
FAQs
What is a fun thing to send to an inmate?
There are multiple fun things to send to an inmate such as greeting cards, drawing from kids and photos of everybody. Some people like games such as Sudoku or word search. You can also opt for a loving note about how what everyone is up to.
What are fun activities for inmates?
Inmates can engage in fun activities like board games, card games, and chess to stay entertained. Many enjoy creative jail letters with word puzzles or drawings from loved ones. Exercise, reading, and writing are also popular ways to pass the time. Some facilities allow inmate talent shows, sports, or hobby classes for recreation.
How can I uplift a man in jail through my letters?
You can uplift a man in jail by writing encouraging and supportive letters that remind him he’s not alone. Share positive updates, inspirational quotes or personal stories to keep his spirits high. Creative jail letters with jokes, word games or drawings can add a fun touch. Most importantly, express genuine care and reassurance that you believe in him and his future.
How do I make an inmate feel special?
You can make an inmate feel special by sending thoughtful letters, photos, or small gifts that remind them they are loved and not forgotten. A support letter to a friend in jail with heartfelt words of encouragement can mean a lot. You can also send prison care packages with snacks, books, or personal items (if allowed). Adding fun surprises like creative jail letters or funny postcards can brighten their day and make them feel valued.
What items can inmates receive?
Inmates can receive letters, photos, books, magazines and approved care packages, depending on the facility’s rules. Some prisons allow prisoner gift sets with hygiene products, snacks or stationery. Inmate gift baskets may include pre approved items like coffee, chips and candy. Always check the prison’s guidelines before sending anything to guarantee compliance.