Writing “Open When” letters for your loved one in prison is a heartfelt way to stay connected and provide emotional support. These letters can bring comfort, joy, and a sense of closeness, helping them navigate the challenges of incarceration. Here are 50 “Open When” letter ideas, each designed to be filled with love, encouragement, and personal touches through words and drawings.

1. Open When You Feel Lonely

Remind them of your love and the cherished memories you share. Include a drawing of a special place you both love.

2. Open When You Miss Home

Describe a typical day at home, capturing the sights, sounds, and smells. Draw a cozy home scene.

3. Open When You Need a Laugh

Share a funny story or joke. Draw a cartoon character or a funny situation.

4. Open When You’re Feeling Down

Write an encouraging note to lift their spirits. Draw a bright sun and happy faces.

5. Open When You’re Angry

Acknowledge their feelings and offer calming words. Draw a peaceful nature scene.

6. Open When You Need Motivation

Include motivational quotes and affirmations. Draw a mountain with someone climbing to the top.

7. Open When You’re Bored

Suggest simple activities they can do. Draw a fun puzzle or maze.

8. Open When You Feel Hopeless

Remind them of their strength and resilience. Draw a phoenix rising from the ashes.

9. Open When You’re Anxious

Share calming techniques and comforting words. Draw a serene beach or a calm forest.

10. Open When You’re Celebrating a Holiday

Describe how you’re celebrating and send festive wishes. Draw holiday decorations.

11. Open When You’re Feeling Overwhelmed

Offer words of support and advice for managing stress. Draw a tranquil garden.

12. Open When You’re Thinking of Our Future

Share your hopes and dreams for the future. Draw a vision of your life together.

13. Open When You’re Missing Our Pets

Write about funny or sweet moments with your pets. Draw a picture of your pets.

14. Open When You’re Missing Our Family

Include updates about family members and fond memories. Draw a family portrait.

15. Open When You Feel Unloved

Reaffirm your love and appreciation. Draw a heart with both of your initials.

16. Open When You Need to Feel Appreciated

List reasons why you appreciate them. Draw a trophy or a medal.

17. Open When You’re Feeling Confident

Celebrate their confidence and achievements. Draw a superhero version of them.

18. Open When You Need a Reminder of Our Love

Recount a romantic memory or gesture. Draw a romantic scene, like a sunset.

19. Open When You Need to Laugh at Yourself

Share a silly memory involving them. Draw a humorous self-portrait.

20. Open When You Need Strength

Remind them of their inner strength and resilience. Draw a strong tree with deep roots.

21. Open When You’re Feeling Grateful

Express your gratitude for their presence in your life. Draw a bouquet of flowers.

22. Open When You Need to Know Someone Cares

Assure them of your care and concern. Draw two hands holding each other.

23. Open When You’re Feeling Nostalgic

Revisit a shared memory from the past. Draw a picture of that memory.

24. Open When You Need a Good Cry

Let them know it’s okay to feel and express emotions. Draw rain turning into a rainbow.

25. Open When You’re Missing Your Favorite Food

Describe the taste and experience of their favorite meal. Draw a delicious-looking meal.

26. Open When You Want to Dream About Travel

Talk about places you want to visit together. Draw a globe with marked destinations.

27. Open When You’re Feeling Proud of Yourself

Celebrate their accomplishments and character. Draw a gold star or a certificate.

28. Open When You Need a Distraction

Suggest mental exercises or stories. Draw a simple crossword puzzle or word search.

29. Open When You’re Feeling Creative

Encourage them to draw or write something. Draw a palette with bright colors.

30. Open When You’re Feeling Frustrated

Offer ways to manage frustration. Draw a calming image like waves on the shore.

31. Open When You Need to Feel Connected

Share a current event or something personal from your day. Draw a connecting line between hearts.

32. Open When You Want to Remember Our Fun Times

Recall a fun outing or adventure. Draw a scene from that day.

33. Open When You Need to Know I’m Thinking of You

Tell them about your thoughts and feelings. Draw thought bubbles with their name.

34. Open When You’re Missing Your Friends

Share updates from mutual friends. Draw a group of friends together.

35. Open When You’re Feeling Adventurous

Suggest ways to explore new ideas or activities. Draw a treasure map.

36. Open When You’re Feeling Artistic

Encourage them to create art. Draw an empty canvas or sketchbook.

37. Open When You’re Feeling Quiet

Share calming thoughts and reflections. Draw a peaceful night sky with stars.

38. Open When You’re Feeling Restless

Suggest ways to channel restless energy. Draw a running track or a calm lake.

39. Open When You’re Feeling Hopeful

Celebrate their hope and dreams. Draw a sunrise over mountains.

40. Open When You’re Feeling Generous

Encourage acts of kindness. Draw a giving tree or helping hands.

41. Open When You’re Missing the Outdoors

Describe a beautiful outdoor scene. Draw a favorite outdoor location.

42. Open When You Need a Hug

Send a virtual hug through your words. Draw arms in a hugging motion.

43. Open When You’re Feeling Reflective

Encourage deep thoughts and reflections. Draw a mirror with a thoughtful face.

44. Open When You’re Feeling Energetic

Suggest ways to use their energy positively. Draw a burst of energy or fireworks.

45. Open When You’re Feeling Playful

Share a fun memory or game idea. Draw playful characters or games.

46. Open When You’re Feeling Tired

Encourage rest and self-care. Draw a cozy bed or a peaceful nap scene.

47. Open When You Need to Know You’re Brave

Remind them of their bravery and courage. Draw a lion or a brave knight.

48. Open When You’re Feeling Inspired

Celebrate their inspiration and ideas. Draw a light bulb or a shooting star.

49. Open When You Need to Know You’re Important

Express their significance in your life. Draw a crown or a shining star.

50. Open When You Want to Celebrate Us

Reminisce about your relationship and shared moments. Draw a picture of the two of you together.

Conclusion

“Open When” letters are a thoughtful and personal way to support your loved one during their incarceration. Each letter can provide comfort, encouragement, and a reminder of your love. Use these ideas to create a meaningful connection through words and drawings, helping them feel supported and remembered no matter the distance.