Connecting through conversation: Holiday questions to bring you closer

The holiday season can be tough when you’re separated from the people you love. For incarcerated individuals and their families, meaningful conversations can offer a sense of togetherness and hope. To help, we’ve created a list of prompts that can be used during visits, calls, or letters. These questions are designed to foster connection, inspire growth, and even bring a little fun to your interactions.

Reflecting on growth

Encourage your loved one to share what’s been meaningful to them:

• “What’s a story or idea you’ve come across recently that inspired you?”
• “What’s one goal you’re setting for the new year, and how can we work toward it together?”

These prompts help focus on personal growth, hope, and future possibilities, reminding them that each step forward matters.

Building support

Create space for honest conversations:

• “What’s been the hardest part of this holiday season for you? How can I support you better?”
• “Is there something specific we could plan together to lift your spirits?”

These questions show you’re listening and ready to provide comfort, no matter the distance.

Finding gratitude

Shine a light on positivity:

• “What’s something you’re grateful for, even in tough times?”
• “What’s a memory or thought that has brought you peace or happiness recently?”

Gratitude can be a powerful way to find joy, even in challenging circumstances.

Adding fun and laughter

Don’t forget to spark some smiles:

• “If you could make up your own holiday tradition, what would it be?”
• “Would you rather have a magical sleigh or a snowman friend? Why?”

Lighthearted prompts help keep the conversation playful and uplifting, offering a welcome escape.

For kids

If kids are visiting or calling, help them feel connected:

• “What’s your favorite thing about the holidays? Is there something you look forward to each year?”
• “If you could invite any animal to our holiday party, what would it be and why?”

These playful prompts encourage creativity and strengthen bonds, even during difficult times.

From incarcerated loved ones

For those inside, showing care for family can also be a source of connection:

• “What’s been a challenge for you this week, and how can I support you from here?”
• “Is there a memory or note I can share to help brighten your day?”

These questions remind families that their love and care go both ways.

Why connection matters

For incarcerated individuals and their families, these conversations are more than just words—they’re a way to keep relationships strong, share hope, and find moments of joy during a difficult season.

At Edovo, we believe that building connections can create ripples of change. A heartfelt conversation can bring comfort, inspire resilience, and reinforce the belief that brighter days lie ahead.

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