Finding genuine connections and sparking meaningful conversations has become a rare art form today. The concept of “Conversation Starters” is not new, but we have positioned them in a way to be used as part of The Unplug Challenges – designed to break the ice and dig deeper into the hearts and minds of those around us.
These conversation starters can be used with a variety of Unplug Project challenges, including:
The Digital-Free Mealtime Challenge
These curated prompts, ranging from light-hearted inquiries to deep questions, are more than just a way to fill silence—they’re a bridge to understanding, empathy, and unexpected discoveries about the people in our lives. Whether you’re gathering with old friends, new acquaintances, or even colleagues, incorporating Conversation Starters into your interactions promises to transform ordinary exchanges into memorable, enriching dialogues. Feel free to drop us an email with your favorite conversation starters.
| What book has significantly influenced your life and why? |
| Describe a memory from your childhood that stands out. |
| What’s a skill you’ve always wanted to learn and why? |
| Discuss a moment in history you would have loved to witness. |
| What does your perfect day look like? |
| Share a tradition from your family or culture. |
| What’s a place you’ve always wanted to visit and why? |
| What’s an unpopular opinion you have? |
| Discuss a movie that changed your perspective on a topic. |
| What are you most grateful for today? |
| If you could have dinner with any historical figure, who would it be and why? |
| What’s a challenge you’ve overcome that you’re proud of? |
| Describe your dream job. |
| What’s your favorite way to unwind after a stressful day? |
| Share an achievement that means a lot to you. |
| If you could instantly become an expert in something, what would it be? |
| What’s a piece of advice you would give your younger self? |
| Discuss a favorite piece of art and its impact on you. |
| What’s a hobby you’ve always wanted to pick up but haven’t yet? |
| Share a goal you have for the next year. |
| What’s a fear you’ve conquered? |
| Describe a moment when you felt truly at peace. |
| What’s something you’re looking forward to? |
| Share a funny or embarrassing moment from your life. |
| What’s a lesson you learned the hard way? |
| Discuss a book or movie that made you cry. |
| What’s a talent you possess that most people don’t know about? |
| If you could live in any era, which would it be and why? |
| What’s the best piece of advice you’ve ever received? |
| Share a moment when you were proud of a friend. |
| What’s an important life lesson you’ve learned? |
| If you could change one thing about the world, what would it be? |
| Discuss a time you helped someone and it made a difference. |
| What’s a song that holds special meaning for you? |
| Share a personal tradition you have for starting the new year. |
| What’s something you wish more people knew about you? |
| If you could have any superpower, what would it be and why? |
| Discuss a cause that’s important to you. |
| What’s a country you’d like to live in for a year and why? |
| Share a moment that took your breath away. |
| What’s something new you’ve learned recently? |
| Discuss a time when you faced a fear. |
| What’s an activity that makes you lose track of time? |
| Share a dream you remember vividly. |
| If you could witness any event past, present, or future, what would it be? |
| Discuss your favorite childhood TV show or movie. |
| What’s something you’ve done that you never thought you would? |
| Share a time when you received unexpected kindness. |
| What’s a quote that inspires you? |
| Discuss a book that you couldn’t put down. |
| What’s a lesson you learned from a failure? |
| If you could send a message to the entire world, what would you say? |
| Share a time when you were moved by someone’s generosity. |
| What’s something you do to make the world a better place? |
| Discuss a moment when you felt incredibly lucky. |
| What’s a project you’re currently working on? |
| Share a time when you tried something outside of your comfort zone. |
| What’s a tradition you’ve started with friends or family? |
| Discuss an unexpected turn in your life that turned out positive. |
| What’s an experience that made you stronger? |
| Share a time when you had to make a tough decision. |
| What’s a belief you hold strongly? |
| Discuss your first memory. |
| What’s a small act of kindness you were once shown? |
| Share an experience where you were completely out of your element. |
| What’s a habit you’re proud of breaking or making? |
| Discuss a time when you felt most alive. |
| What’s a risk you took that paid off? |
| Share a personal victory, big or small. |
| What’s a piece of wisdom you live by? |
| Discuss an experience that changed your outlook on life. |
| What’s an act of self-care you find really effective? |
| Share a time when you connected with a stranger. |
| What’s a goal you recently achieved? |
| Discuss a moment of unexpected joy. |
| What’s something you’ve forgiven yourself for? |
| Share a lesson you learned from nature. |
| What’s a book that has profoundly affected your life? |
| Discuss a time when you stood up for something you believe in. |
| What’s a random act of kindness you’ve experienced or witnessed? |
| Share a personal milestone and what it meant to you. |
| What’s a habit that has significantly improved your life? |
| Discuss a time you were grateful for something small. |
| What’s a place that feels like home to you, and why? |
| Share an instance where a first impression was completely wrong. |
| What’s a word or phrase that you live by? |
| Discuss a cultural experience that opened your eyes. |
| What’s a challenge you’re currently facing? |
| Share a favorite family recipe or meal. |
| What’s something that always brings a smile to your face? |
| Discuss your favorite way to spend a day off. |
| What’s an important value you try to live by? |
| Share a time when you were surprised by your own strength. |
| What’s a piece of art (music, painting, film, etc.) that has touched you? |
| Discuss an experience that taught you patience. |
| What’s a memory that makes you happy whenever you think about it? |
| Share an experience that taught you the importance of community. |
| What’s a personal rule you never break? |
| Discuss a time when saying ‘no’ was the best decision you made. |
| What’s a skill or talent you admire in someone else? |
| Share your thoughts on what makes a house a home. |
| What’s an experience that made you appreciate life more? |