Maintaining a deep connection with your partner during incarceration can be challenging, but shared journaling offers a creative way to bridge the distance. This 30-day guided journal project is designed for couples to work on in parallel: both partners respond to the same daily prompt separately in their own journals or letters, without exchanging answers until the end of the 30 days. On day 30 or 31 (or whenever you complete the challenge), you’ll exchange what you’ve written – through mail or during a visit – allowing you both to read each other’s heartfelt responses. This exchange can be a beautiful, intimate moment of discovery, almost like opening a time capsule of the last month’s thoughts.

Why try a couples journaling challenge? Relationship experts and veteran prison couples alike find that answering prompts “together” (even while physically apart) fosters open communication and deeper understanding between partners. By writing about your feelings, memories, and hopes, you’re essentially having a month-long dialogue on paper. When you finally share your answers, you’ll each gain insight into the other’s inner world – what they struggled with, what kept them going, how they feel about you, and more. It creates a shared experience despite the separation, helping you both feel more connected and “in sync” emotionally. In fact, there are published couples’ journals (like Our Q&A a Day: 3-Year Journal for 2 People) that follow this concept – each person answers one question per day and periodically they share their answers, often via letters or during visits (chaptersandchains.com.) Such practices have been praised as a wonderful way to continue learning about each other and maintaining intimacy over distance (chaptersandchains.com.)

How to Do It: First, coordinate with your partner so you both have the list of prompts (you can send the list in a letter, or if phone calls allow, read them out). Each of you should commit to writing a short entry every day addressing that day’s prompt. You might use a notebook, a blank journal, or even loose pages – whatever is accessible (for the partner on the inside, make sure any journaling complies with facility rules). Write honestly and in detail, as if you’re speaking to your loved one, but hold onto your answers rather than mailing them daily. The understanding is that you’ll share everything at once at the end. Knowing that you’ll exchange journals later may encourage you to be thoughtful and heartfelt in your responses, and also gives you something exciting to look forward to together.

Throughout the month, it might help to know that your partner is reflecting on the same question each day. Some couples find comfort in imagining what the other might be writing in that moment, almost like you’re having a silent conversation each night. If one of you falls behind a day or two, it’s okay – this project is flexible. The goal is not perfection, but connection. When day 30 comes, you can either swap journals in person (if you have a visit around that time) or mail your written pages to each other. Then, take a day to read and absorb your partner’s words. You could even schedule a phone call or video visit afterward to talk about what you learned from each other’s entries. Couples who have done similar exercises often report feeling rejuvenated in their relationship, because it sparks new conversations and a deeper appreciation for one another’s experiences and feelings.

The tone of this couples journal can be whatever suits you both – a mix of romantic, nostalgic, humorous, spiritual, and therapeutic. We’ve balanced the prompts to include positive memories, expressions of love and gratitude, personal growth, and future hopes. Feel free to adapt any question to better fit your relationship. What matters most is sincerity. By the end of 30 days, you’ll have created a meaningful collection of writings that document your journey as a couple during this time apart – truly a treasure to cherish.

30 Daily Couples Prompts (to be answered by each of you):

1. Day 1: “What do you love most about your partner?” – Start the challenge on a loving note. Each of you write about the core qualities or little things you absolutely love about the other. Be specific and heartfelt: maybe it’s their sense of humor, their patience, the way they always support you, or even a favorite quirk. Sharing these responses later will remind you both why your bond is worth every hardship.
2. Day 2: “Describe a favorite memory you share together. Why is it so special to you?” – Take a trip down memory lane. It could be the day you first met, a special date or anniversary, or even a simple quiet moment that meant a lot. Paint the picture of that memory and explain what feelings it brings up. When you read each other’s favorite memories, you might be happily surprised or touched to see which moments the other cherishes most.
3. Day 3: “What is something your partner does (or did before) that always makes you smile?” – Think about those gestures, habits, or routines that your partner has which never fail to brighten your day. It could be how they leave you sweet notes, their goofy dance when they’re excited, or how they say “I love you” in a unique way. Even though you can’t experience some of these things in person right now, recalling them will bring a smile as you write – and your partner will love reading about the joy they bring you.
4. Day 4: “In what ways has your partner changed your life for the better?” – Reflect on personal growth and positive changes that came from having your loved one in your life. Maybe they inspired you to pursue a goal, helped you overcome a fear, or simply taught you the meaning of true love and loyalty. This prompt lets you express gratitude for the impact you’ve had on each other. It’s powerful to realize and acknowledge how you’ve helped shape one another’s lives.
5. Day 5: “What do you admire about how your partner is handling this challenging situation?” – Both of you are showing strength in different ways. Write about how you see your partner’s strength during the incarceration. For example, the partner on the outside might admire the resilience or positivity of their incarcerated loved one; the partner on the inside might admire the loyalty, patience, or resourcefulness of the one waiting. Highlight the coping mechanisms or attitude your partner has that you find admirable. These words of affirmation will be incredibly uplifting to read later, reinforcing that you notice and value each other’s efforts.
6. Day 6: “What do you miss the most about your partner’s presence?” – It’s okay to be honest about the ache of missing each other. Describe the specific things you long for: Is it the way they hug you, having them beside you at night, cooking together, or even the sound of their laughter in person? By articulating what you miss, you also acknowledge how much you cherish those aspects of your partner. Reading this might be bittersweet, but it also reaffirms the depth of your connection.
7. Day 7: “What is something you have learned about yourself during this time apart?” – Shifting to a bit of self-reflection, consider personal lessons from this experience. Maybe you’ve discovered you’re more patient than you thought, or you learned how to budget better, or realized the depth of your own emotional strength. Each of you share at least one thing you’ve learned about yourself. This helps both partners see how this challenge is shaping each of you individually. When exchanged, it can lead to supporting each other’s continued personal growth.
8. Day 8: “What is something new you’ve learned about your partner during this time?” – No matter how well you know each other, being apart can reveal new facets. Perhaps through letters and phone calls, you’ve seen a more vulnerable side of your partner, or learned about a new interest they’ve developed, or witnessed them handling adversity in a way that impressed you. Write about any new insights or surprises about your partner. It shows that even in separation, you’re continuing to get to know each other on a deeper level.
9. Day 9: “Recall something that made you laugh or smile recently. Describe it so you can share that moment with your partner.” – Think of a light-hearted prompt: maybe a funny incident, a joke you heard, a positive moment from your day or a TV show that cracked you up. Write it down as if telling your partner the story. Life in these circumstances can be heavy, so sharing humor or joy is a way to feel normal together. When you exchange journals, you’ll each get to experience those little joyful moments the other had, almost as if you were there to share the laugh.
10. Day 10: “How do you feel you two stay connected despite the distance? What do you do (or think about) to maintain that connection?” – Reflect on the strategies or rituals that help you feel close. Maybe it’s writing daily letters or frequent emails, having scheduled calls, saying prayers for each other, or even looking at the moon at the same time. Each of you describe what makes you feel connected. You might also mention any mental or emotional habits – like talking to your partner in your head when something happens, or keeping a journal of things to tell them. Later, seeing how your partner feels connected will reassure both of you that the bond remains strong, even when apart.
11. Day 11: “Share a dream or goal you have for your future together.” – Look ahead and write about one specific dream for the two of you. It could be something short-term (like taking a weekend trip after release, or having a special date night out) or long-term (like building a home, starting a business, raising a family, renewing your vows, etc.). Describe why this goal matters to you and how you picture it unfolding. Dreaming together is a way of creating hope and giving yourselves a shared vision to hold onto.
12. Day 12: “If you could spend one day together right now without any restrictions, what would you do?” – Let your imagination run. Plan out an ideal day from morning to night as if distance and rules weren’t an issue. Would you sleep in and then make a big breakfast? Go for a walk in the park holding hands? Visit favorite places or people? Maybe just curl up and watch a movie together at home. Each of you sketch out this fantasy day in detail. When you read your partner’s version, it will be heartwarming to see what their idea of a perfect day with you looks like – and you might find you chose similar simple pleasures.
13. Day 13: “What are you most proud of about your partner?” – Take this day to give your partner the gift of knowing what you truly admire in them. It could overlap with Day 5, but you can broaden it: maybe you’re proud of how hard they’re working on self-improvement, or how kind and supportive they are to others, or how they’re managing a job or classes from inside, or how the one outside is holding the family together. Write about at least one thing (or several) that fills you with pride when you think of your partner. This will surely boost each other’s spirits when exchanged, showing that you see the best in one another.
14. Day 14: “What do you think your partner is proud of about you?” – This one flips perspective. Put yourself in your loved one’s shoes and guess what they might list as your strengths or accomplishments. It might feel a bit odd to “praise yourself” in this indirect way, but it encourages you to see yourself through your partner’s loving eyes. For instance, “I think he’d say he’s proud of how I’m keeping the household running,” or “She’s told me she’s proud of me for staying positive, so I’ll write about that.” When your partner reads it, they can see if you guessed right – and maybe even add more to it! It’s a sweet way to acknowledge that you value each other’s opinions and know that you are valued.
15. Day 15: “Describe a difficult moment you faced recently and explain how thoughts of your partner (or something they’ve said or done) helped you through it.” – Life apart is filled with challenges for both of you. Each of you, recount a specific tough day or incident (it could be an emotional low, a conflict, a health scare, anything) and then focus on how your partner’s presence in your life helped you cope. Maybe remembering a piece of advice they gave, or their love gave you strength, or you didn’t want to worry them so you persevered. This prompt highlights the support you give each other emotionally, even when you’re not physically together. Reading about how you helped your partner through a hard time – often without even knowing it – will reinforce the meaningful impact you have on each other’s lives.
16. Day 16: “Is there anything you want to apologize for or regret not saying/doing in your relationship? Express it here.” – Every relationship has moments of regret or things left unsaid. Use this as an opportunity to be vulnerable and clear the air if needed. Perhaps one of you wants to apologize for a past argument, for not being as open about feelings, or for a specific mistake. It could also be regret like “I’m sorry I didn’t fully understand what you were going through earlier” or “I regret that we didn’t have more time together before this happened.” Frame it in a loving way, focusing on your feelings and accountability. These apologies, when exchanged, can be healing. They show that you’re reflecting on how to be a better partner and that you care about the other’s feelings deeply. (Remember to stay constructive – this isn’t meant to dredge up old fights, but to show humility and love.)
17. Day 17: “What are you grateful for in your relationship right now, despite the challenges?” – It’s important to recognize the positives even in hard times. List a few things about your relationship that you’re thankful for today. You might be grateful for the constant love and loyalty, for the communication you do have (letters/phone), for shared laughter, for the growth it’s bringing, or even simply that you have each other to love. Focusing on gratitude can improve your mood and perspective. When you share this, it will reassure each of you that the other still sees the good in your relationship, despite the prison walls.
18. Day 18: “Name three things you appreciate about your partner’s personality or character.” – A bit like Day 1 but more structured. Write down three distinct qualities or character traits your partner has that you truly admire. For example: their honesty, their creativity, their spirituality, their sense of humor, their kindness, etc. For each trait, add a sentence or two about why you value it or a time when they showed that trait. This paints a loving portrait of who your partner is at their core. It’s essentially giving them sincere compliments in written form – something that will surely make them feel loved and seen when they read it.
19. Day 19: “How have you grown as a person during this time apart?” – Revisit personal growth, but now share it with your partner. In Day 7 you reflected privately on what you’ve learned about yourself; now articulate to your partner how you feel you’ve grown. Maybe you’ve become more patient, more resilient, more independent, or more understanding of something. This is a chance to let them know that while this situation is not what either of you wanted, you are trying to make the best of it by improving yourself. It also invites them to celebrate that growth with you. Your partner will likely feel proud and happy to read about the positive changes you’re making (and it might inspire them to share their own growth).
20. Day 20: “What have you learned about love or commitment from this experience?” – This prompt encourages both of you to reflect on the bigger picture of your relationship. Perhaps you’ve learned that love can endure more than you thought, or that commitment means showing up even when it’s tough. Maybe you learned the importance of communication, trust, or forgiveness on a whole new level. Write about the lessons this challenge has taught you about what it means to love someone. When you exchange answers, you’ll see how aligned your feelings are on what your relationship stands for, and it can spark a thoughtful conversation about how this journey is shaping your shared values.
21. Day 21: “How do you envision your first week together after release?” – Get excited and paint a picture of that reunion period. It might be daydreaming, but it’s also a way to set positive expectations. Describe what the first week or days would ideally be like: maybe simple pleasures like eating favorite meals together, taking a walk, lots of catching up talks, spending time with family, or just quiet alone time without saying a word, enjoying each other’s company. Be as detailed or as broad as you like. The incarcerated partner might focus on freedom elements (like seeing the sky freely, visiting meaningful places together), and the outside partner might focus on having their loved one back in daily life. Reading each other’s hopes for that time will give you both a warm feeling and a mutual goal to look forward to.
22. Day 22: “What gives you hope about your future together?” – Both of you reflect on why you believe in your future as a couple. Maybe it’s the strength of your love shown through this ordeal, the plans you’ve made, the personal growth you’re undergoing, or even faith/spiritual convictions that comfort you. You could write about expecting better days, the support you have, or simply the feeling in your heart that this is meant to last. By identifying why you remain hopeful, you reinforce that optimism for both of you. Exchanging these thoughts will undoubtedly reinforce a shared sense of hope, which is vital for getting through the challenging times.
23. Day 23: “Write a short love letter to your partner, expressing whatever is on your heart today.” – Take a break from structured questions and just speak from the heart directly. Begin with a greeting like “Dear ___,” and let the words flow. You can profess your love, talk about how much you miss them, encourage them, or mention anything you haven’t yet in the prompts. Think of this as a standalone love letter – something that, if this were the only page they got to read, would make them feel loved and cherished. There’s no strict topic; it’s about emotional expression. (Since you’ll exchange journals, this letter will reach them – so it’s a beautiful chance to say all the loving things you want them to know.)
24. Day 24: “What is something new or special you want to experience together in the future, and why?” – This could be an event, an activity, or a milestone. Perhaps you’ve always talked about traveling to a particular place, or you want to renew your vows or simply start a tradition like weekly date nights at home. Each of you choose something (or a few things) that you really look forward to doing with the other when circumstances allow. Explain why it’s meaningful to you. Dreaming up new experiences adds to your list of shared goals and keeps the relationship forward-looking and dynamic, rather than feeling stuck in pause.
25. Day 25: “How has your communication with each other changed during this period? What have you improved or come to appreciate about how you communicate?” – Being forced to communicate through letters, short calls, or limited visits can be tough, but many couples discover new ways to connect. Maybe you’ve gotten better at expressing feelings in writing, or you don’t take conversations for granted anymore. Perhaps you’ve developed code words or rituals (like saying “goodnight” through the stars). Each of you reflect on how your style of communication or understanding of each other’s communication has evolved. Are you more patient now? More honest? Did you learn to listen more carefully? Write about the positive changes or even the challenges that remain. This can lead to an appreciation of the effort you both put into staying in touch and may highlight things you want to continue (like letter writing) even after release.
26. Day 26: “What is a promise or commitment you want to make to your partner for the future?” – Think in terms of vows or assurances, big or small. Maybe you promise that you will always stand by them, or to work on a specific issue (like controlling temper, or being more open about feelings). It could be a promise to prioritize family time, to keep honest communication, or to never lose hope in each other. By writing this, you’re essentially renewing your commitment despite the hardships. When exchanged, these written promises can be very touching – they are like your personal pledge of loyalty and love going forward.
27. Day 27: “What keeps you going on the hardest days? Share a source of strength or comfort that helps you persevere.” – Each of you write about a go-to coping mechanism or inspiration. It might be a mantra you repeat, a prayer, thinking of your partner’s smile, focusing on future plans, or family responsibilities that motivate you. Maybe it’s a mental image, like picturing a reunion hug, or advice someone gave you. By sharing this, you let your partner know what sustains you when you’re down. It might reveal new ways you can support each other too (for example, if one says “thinking of how she needs me to be strong,” the other will know that their dependency is giving strength). It’s an intimate look at your inner worlds in tough moments.
28. Day 28: “If you had to pick a song (or a book, or a quote) that represents your relationship or your feelings right now, what would it be and why?” – This is a creative prompt to tap into artistic or symbolic expression. Maybe there’s “your song” as a couple, or a new song that one of you heard that feels fitting. Or a poem, book, or movie that resonates with what you’re going through. Write down the song/quote and the artist/author, and explain what about it reminds you of your partner or your situation. (“This Too Shall Pass” might be your motto, or a song like “Thinking of You” that you play often, etc.) This prompt might introduce each other to meaningful media that you can then both embrace. And it’s a window into how each of you interprets your journey through art or literature.
29. Day 29: “In what ways do you maintain trust and faith in each other during this separation?” – Trust is key in any relationship, especially under strain. Explain how you personally work to maintain trust in your partner. Do you remind yourself of their honesty or past behavior? Do you avoid rumors or shut down negative thoughts? Perhaps you both have made transparency a priority (sharing updates about daily life, being open about feelings). Also, mention how you keep faith in the relationship – maybe through affirmations, prayer, or simply a gut feeling that your love is unshakable. By writing this, you also reassure your partner of your fidelity and commitment. When exchanged, it serves as a mutual recommitment to trust, helping alleviate any anxieties either of you might have had.
30. Day 30: “Write a message of encouragement to your partner for them to read whenever they need a boost.” – As the final entry, end on a supportive and loving note. Think of this like writing a pep talk or words of comfort directly addressed to your partner. You could remind them of their strengths, express your confidence in getting through this together, and highlight how much they mean to you. For example, “No matter what happens, I want you to remember how strong you are and how much I believe in us…” or “When you feel down, I hope you read this and know you’re not alone – I’m always with you in heart.” Make it as heartfelt and motivating as possible. This page will be something your partner can reread whenever they need encouragement, and vice versa. It’s like giving each other a loving push to carry on, which is a beautiful way to conclude the 30-day project.

Completing the Exchange: Congratulations on finishing the 30 days! On day 30 or 31, exchange your journal entries (through mail, or in person). Take your time to read through your partner’s answers. It might be emotional – you’ll likely laugh, cry, and smile seeing their thoughts corresponding to each day. Make sure to acknowledge what you’ve learnedfrom their writing: perhaps in your next letter or call, discuss a few prompts that stood out. This exchange isn’t the end of the conversation – it’s the beginning of a deeper one. You may find that some of their answers spark new questions or topics for you to explore together, which is wonderful. Couples who engage in these kinds of reflective exercises often find that it deepens their intimacy and renews their sense of teamwork in facing the future.

Lastly, consider what you’d like to do after this project. You could continue with your own prompts, swap roles and ask each other new questions, or even turn this into a regular ritual (some couples do a weekly “question of the week” in letters). The key takeaway is that intentional communication like this keeps your relationship strong. By actively focusing on your love and future, you’ve created a shared narrative of hope and commitment. As one prison wife who created a couples journaling workbook put it, exercises like these help “create shared experiences despite the distance” and nurture intimacy and understanding for the future.

In summary, journaling – whether individually or as a couple – can be a lifeline during the incarceration journey. It offers a safe outlet for your emotions, reduces stress, and helps you discover inner strength. For couples, it keeps the wheels of communication turning and reassures both partners that love endures even behind bars. We hope these 30-day challenges bring you clarity, comfort, and closeness. ❤ Remember, each day you write is an act of love – for yourself and for each other. Stay strong and keep journaling your way through to brighter days ahead.

Sources:

• Mental Health America – “Someone I love is in jail”: coping advice for family members (recommends journaling feelings and gratitude) screening.mhanational.orgscreening.mhanational.orgscreening.mhanational.org.
• University of Rochester Medical Center – “Journaling for Emotional Wellness”: on journaling’s benefits for managing anxiety, stress, and creating order from chaos urmc.rochester.eduurmc.rochester.eduurmc.rochester.edu.
• PositivePsychology.com – “30 Best Journaling Prompts for Improving Mental Health”: notes that guided prompts enhance self-reflection and emotional regulation positivepsychology.compositivepsychology.com.
• Chapters & Chains blog – “Locked in Love: Book Suggestions for Prison Wives and Girlfriends”: mentions Q&A a Day couples journal (daily questions exchanged via letters/visits) chaptersandchains.com.