Chatting with friends online can be a blast—but coming up with fresh topics isn’t always easy. Whether you’re catching up with a long-distance pal, bonding with a gaming buddy, or getting to know a new coworker over Slack, the right question can spark laughter, connection, and memorable conversations.
Below, you’ll find over 80+ conversation starters that will help you beat awkward silences and deepen your digital friendships. Don’t forget to respect each other’s comfort zones; skip any prompts that feel too personal.
Table of Contents
Quick Icebreakers
Why these matter: Fast, light questions get the ball rolling without feeling heavy.
- What’s the most interesting thing you’ve read online recently?
- If you could travel anywhere in the world right now, where would it be and why?
- Do you have a favorite quote or saying?
- What’s one fun fact about yourself that most people don’t know?
- If you could have dinner with any celebrity, who would it be?
- Have you watched any good movies or shows lately?
- Are you a morning person or a night owl?
- What’s something you’re looking forward to this week?
- What’s a hobby you secretly want to pick up but haven’t tried yet?
- Share the funniest autocorrect fail you’ve ever sent.
Pro-Tip: Use Emojis & GIFs: A quick 😄 or 🎉 can lower the barrier to reply and keep it light.
Hobbies and Interests
Why these matter: Discover shared passions and spark plans to try new activities together.
- What hobbies are you passionate about?
- Have you picked up any new skills or hobbies recently?
- Do you enjoy cooking or baking?
- Do you play any musical instruments?
- Are you into any sports or physical activities?
- Do you enjoy painting or drawing?
- Have you ever tried a new hobby and totally loved it?
- What’s your favorite type of craft or DIY project?
- Are you a fan of video games? Which ones?
- What’s a conspiracy theory you kind of believe, just for fun?
Favorites and Recommendations
Why these matter: Everyone loves to share their go-to picks—and you might discover something new.
- What’s your all-time favorite movie and why?
- Do you have a favorite book you’d recommend?
- What’s your go-to comfort food?
- Do you have a favorite band or musician?
- Any podcast recommendations?
- What’s your favorite board game or card game?
- Is there a product you love and can’t live without?
- Have you found any good YouTube channels recently?
- Which app on your phone do you use the most?
- What’s a childhood memory that still makes you smile today?
Pro-Tip: Share album covers, book jackets, or food photos to spark visual interest.
Deep & Meaningful Questions
Why these matter: Vulnerability fosters trust and a deeper connection—use sparingly and only when your friend is comfortable.
- What’s the best advice you’ve ever received?
- Can you tell me about a time when you faced a significant challenge and overcame it?
- What’s a moment that changed your life forever?
- Do you have a personal mantra or slogan?
- What inspires you when things get tough?
- Who is someone you look up to, and why?
- What change would you like to see in the world?
- What’s one mistake you made that taught you a valuable lesson?
- What small act of kindness has someone done for you recently?
- What’s the best advice you’ve ever ignored—and regretted it?
Life Experiences
Why these matter: Reminiscing about past experiences helps you find common ground and surprising stories.
- What was your favorite trip or vacation ever?
- Have you ever moved to a new city or country?
- What’s the funniest thing that ever happened to you?
- Have you ever participated in volunteer or charity work?
- What’s the most spontaneous thing you’ve ever done?
- Do you have any interesting family traditions?
- What’s something you did that you’re really proud of?
- Have you ever met someone famous?
- What’s a childhood mishap you can now laugh about?
Travel & Adventure
Why these matter: Shared wanderlust can lead to future travels—or at least fun “would-you-rather” scenarios.
- What’s your favorite travel destination and why?
- Do you prefer beach vacations or mountain getaways?
- Have you ever traveled solo?
- What’s the most beautiful place you’ve ever visited?
- What’s the best food you’ve tried while traveling?
- Is there a place you’ve always wanted to visit?
- Have you ever had travel plans go hilariously wrong?
- What’s the first trip you remember taking?
- What’s your favorite mode of transportation for travel?
- If you could teleport anywhere right now, where would you go?
Dreams & Aspirations
Why these matter: Talking about hopes and goals can strengthen support and accountability.
- What are some of your biggest goals for the next five years?
- If you could achieve any dream, what would it be?
- Do you have a dream job?
- What’s a skill you’ve always wanted to learn?
- Do you have a bucket list? What’s at the top of it?
- If time and money were no object, what would you do?
- Do you have any long-term personal projects?
- What’s something you hope to accomplish this year?
- Who is someone you’d love to go into business with?
- What’s a dream you’ve had since childhood?
Pro-Tip: Celebrate Milestones: When they share progress, acknowledge it (“That’s huge—congrats!”).
Current Events & Trends
Why these matter: Staying on the same page about news and trends makes for lively, relevant chats—always be mindful of sensitive topics.
- What do you think about the latest trending topic on social media?
- Have you tried any cool new apps recently?
- What’s your opinion on the current fashion trends?
- Have you seen any viral videos that made you laugh?
- What’s your take on the latest movie releases?
- How do you feel about the current events in sports?
- Have you participated in any online challenges?
- What’s a recent event that moved or inspired you?
- What’s your take on a recent scientific discovery?
- Which influencer or blogger are you following right now?
Would You Rather
Why these matter: Fun hypotheticals encourage creativity and quick thinking.
- Would you rather always have to whisper or always have to shout?
- Would you rather explore space or the deepest parts of the ocean?
- Would you rather give up social media or give up dessert forever?
- Would you rather time-travel to the past or the future?
- Would you rather be able to talk to animals or speak every human language?
This or That
Why these matter: Quick, binary choices are perfect for rapid back-and-forths or group chats.
- Coffee or tea?
- Mountains or beach?
- Books or movies?
- Early bird or night owl?
- Sneakers or sandals?
Pro-Tip: Great for group chats—see how friends cluster around certain options.
Final Thoughts
A great conversation starter is more than just a question—it’s an invitation to share, listen, and connect. Use these prompts as a springboard, adapt them to your personality, and watch your online friendships blossom.
Remember: the best chats happen when both people feel comfortable and curious. Now, pick a question and start typing!
