Conversation Starters for Friends Online: 7 Original Strategies

Discover 7 engaging approaches to conversation that will help you spark interesting and meaningful discussions with your friends.

Questions are the most versatile tools in our social toolkit. They help us connect seemingly disparate ideas and pull others that seem closely related apart. Questions come in all shapes and sizes, forming pathways between where we currently are and where we want to be. 

It should come as no surprise, then, that questions hold the key to understanding the basis of social engineering. At the foundation of all our social interactions lies a basic level of engagement that stems from necessity (making conversation with the supermarket check-out operator), curiosity (asking every doggo owner you meet all there is to know about their pup) or a desire for connection.

But no two interactions are the same. So, how can the different types of questions and conversation starters you regularly engage with set the tone for new digital connections and friendships? Let's explore seven original strategies for social probing and opening up a diverse sphere of interactions. 

7 Good Reasons To Ask Better Questions

From a friendship-building perspective, asking questions facilitates deeper understanding and more meaningful connections between individuals. So let's explore how questions and conversation starters for friends serve as vehicles, leading us to different types of connections in online and in-person relationships. 

Graduating Questions

When we say graduating questions, we're talking about transitioning from classic ice-breaker convos to more intermediate discussions to deeper dives and stronger bonds. Better yet, we're talking about using questions to establish each stage of connection, as well as transition to the next. 

For instance, shifting conversation topics from an open-minded “So, what's been keeping you busy today?” to a more trust-centered “What kind of internal challenges or wins does this bring up for you?” requires a clear strategic transition. Here's how it works: 

Icebreaker Questions

It can be easy to underrate the ol' icebreaker conversation starter. Yet, these set the foundation for the rest of the chat, and often in the early stages of a friendship, the entire relationship. Keeping questions open at this stage allows more space for the other person to contribute to the direction of the conversation. For example: 

• What's your favorite thing that's happened so far this week?
• When was the last time you had a good belly laugh?
• When was the last time nature left you in awe?

These questions work because they're lighthearted but require some character to shine through from the person answering. They focus on the positive and, in some cases, require a deeper connection to the intellect or fond memories. This shows you're willing to ask stimulating questions and probably value humor, intelligence and sharing. 

Listen carefully to the answer and see if you can ask a few follow-up questions to substantiate the conversation and your understanding. 

Exploring the Shallows

Once you've gotten to know your conversation partner a little better, you can ask questions that require a touch more personal introspection and sharing of their inner world. Take the tortoise approach, rather than the hare. Too much too soon may feel overwhelming — plus, you'll want to leave some stuff for subsequent conversations! Here are a few questions to help take you beyond the icebreaker:

• What was the last memorable dream you had?
• If you could go anywhere or do anything in the world right now, what would you choose?
• What's a book or movie character that's had the biggest impact on your life, and why?

Deeper Waters

When you have established trust and rapport, gently guide the conversation into deeper topics. Since all connections are unique, there's no timeframe on this one. However, to keep things feeling natural, it's best to save these more personal questions for later in the conversation — especially if it's your first time chatting.

• What role do you think luck plays in a person's success?
• What is a lesson you've recently learned?
• How do you envision your life five years from now?

Finding Common Ground

The right conversation starter will set you up with plenty of material to explore common ground as your relationship evolves. But common ground isn't always about vibing to the same music or the hottest binge-worthy series. Sometimes it's about shared values, experiences or goals. Here are a few ways questions can help you explore common interests and invite more meaningful conversation — beyond a shared love of lasagne. 

Personal Reflections

What better way to bond with someone than realizing you think about certain things in the same way? Whether discussing education across the ages, the inclinations of a spicy brain or simply agreeing that rain's not so bad after all, get to know what makes the other person tick under the hood with questions that encourage self-discovery and sharing personal experiences:

• What's something you've always wanted to try but haven't?
• What's one popular opinion you straight-up disagree with and how did that perspective form?
• What is a powerful experience or favorite memory from the past year and what did it teach you?

Shared Values

Values come down to the core of what drives and motivates us in life. For some, it's family and community, while for others it may be the quest for knowledge or owning nice things. Sharing similar values often indicates that your perspectives align, even if your personalities and backgrounds are completely different, offering new points of connection. Explore common values by asking: 

• What are the values that guide your decisions in life?
• What experiences have shaped your view on happiness the most?
• What advice has a good friend offered you and how has it shaped you?

Future Aspirations

A good conversation starter that focuses on dreams and goals creates opportunities for developing friendships to support each other. Plus, how fun is it to dream big and share future plans with somebody new? Inspire your conversations with visionary questions like:

• When you're 50 years old, what are the three things you'd like people to know you for?
• What's one characteristic a loved one has that you'd like to embody in the future? 
• If there was nothing standing in your way, how would you design the next year of your life? 

Emotional Check-Ins

One of the top qualities of a solid friendship is offering one another emotional support — in whatever capacity we can field at the time. Whether you're starting up a conversation with a girl or want to tap into new dimensions with a guy, social and emotional support is a driver that keeps the reciprocity flowing. Questions invite a way to share struggles and seek ways to offer support in two core ways: 

Create a Feelings Focus

In a new online friendship, diving into the deeper shades of our friend's emotional worlds may require a little more warming up — especially in the trust department. You can segue into emotionally supportive conversations by asking more objective and less directed emotionally based questions, for example:

• How do you handle negative emotions when they arise?
• What's your favorite way to recharge when you're feeling overwhelmed or stressed?
• How do you usually celebrate small wins or personal achievements? 

Supportive Conversations

Conversation starters that gauge current emotions help us better understand our friendships. They allow us to be present through the lows, bask in glowing vibes during the highs and affirm that we're in it together — regardless of how either is feeling on any given day. Explore and support your new friend's emotional worlds with questions like: 

• What are three things you wish more people understood about you?
• What's the most important thing in your life right now?
• Are there any ways I can be a better friend to you at this time?

Storytelling Angle

We all have that one friend who can pull out the most inappropriate and funny stories at the best times. What's even better is that there are ways to use questions and conversation openers in your chats to encourage deeper bonds through storytelling. They are: 

Questions That Lead to Stories

Frame questions that encourage sharing stories. Sometimes it's as much about how you ask as what you ask. For instance, beginning with “Tell me about…” semantically invites someone to share with you. Alternatively, outright asking for storytime (plus listening actively and responding) can get people yapping. Below are some examples:

• What was your favorite place to go on holiday as a kid and what did you love about it?
• Can you tell me about an experience that pushed you out of your comfort zone? 
• What's something you now do or know that would make your younger self proud? 

Lessons Learned

Questions that prompt reflections on challenges and lessons learned from past experiences invite new storytelling and an opportunity to explore shared values and common ground. Be gentle going into these: Some people will still be moving through lessons, so remain compassionate and respectful.

• What's a piece of advice you've received that changed your perspective? 
• What's a lesson you've learned from a failure that still resonates with you? 
• What personal challenge have you faced that taught you the most about yourself?

Cultural Exchange

If there's one thing asking questions on a one-to-one video chat platform can give us, it's a solid cultural exchange. This is especially powerful when deep in conversation with someone on the other side of the world. New perspectives and major or subtle cultural shifts impact how we think, experience and live. Cherish these differences and explore how to talk to anyone with questions like:

Exploring Backgrounds

Keep an open mind as you explore how many ways your experience and worldviews differ from conversation partners. It doesn't matter how close or far apart your cultures are — there will be differences. Embrace diversity by asking: 

• What does true freedom mean to you, and how do you pursue it?
• What role does gratitude play in your life, and how do you express it? 
• What's one belief you hold that you think most people disagree with? 

Influential Media

We've all read at least some books, watched movies and listened to music that shaped our perspectives. But much of the media we're exposed to is culturally connected — especially when we can access translated works from different cultures. Explore international perspectives and personal influence with your new online friend with questions like:

• Is there a piece of media from another culture that's shaped how you view this world? If so, what was it?
• How would you describe the media that comes from your country or culture to someone who had never been exposed to it? 
• Who are your favorite filmmakers/comedians/writers/musicians/artists from your country and what do you love about them?

Creative Prompts

Funny conversation starters and thought-provoking questions encourage us to embrace a more silly, light-hearted vibe while breaking outside the box of conventional small talk. Injecting a little imagination can help steer the chat into fresh, fun territory. Whether you're chatting with someone new or deepening a connection with an old friend, creative prompts encourage playful thinking and keep the convo light. 

Imaginative Scenarios

Dive into hypothetical questions that allow your friend to explore fantastical or quirky situations. These prompts break the ice and invite laughter, bonding and a glimpse into their creative side. Try questions like:

• If you could invent a new holiday, what would it celebrate, and how would people observe it?
• Imagine you wake up one day with a superpower — what is it and what’s the first thing you’d do?
• If you could live in any fictional universe, which would you choose, and why?

Future Focus

Ask your friends to dream big or consider their aspirations in a playful way. Help explore who they are while keeping the conversation forward-looking and engaging.

• What’s one invention you hope exists in the next 50 years?
• If you could time travel to any moment in the future, what would you want to see?
• Imagine you’re planning the ultimate bucket list trip — what’s the first thing you add?

Reflection and Action

Reflecting on past experiences and discussing ways to use those insights in the future can bring an entirely new depth to your conversations. These conversation starters balance the personal with the practical, helping your online friendship evolve into something more meaningful.

Past Reflections

Ask questions that guide your friend to reflect on their journey and share stories that have shaped who they are.

• What’s a childhood memory that still makes you smile?
• Looking back on the last year, what decision are you most proud of?
• What’s a moment that taught you something you’ll never forget?

Future Applications

Steer the conversation toward insights from the past and apply them in the present. This opens the door to exploring dreams, goals and shared values.

• What’s one habit you’d like to develop over the next year and why?
• How do you see yourself using what you’ve learned from past challenges to achieve your goals?
• What’s a skill or hobby you’ve always wanted to try, and what do you feel is stopping you?

Spark Deeper Connections on Azar

No matter which route you take to foster meaningful friendships online, remember that dynamic questions pave the way for unforgettable conversations. The more you explore, the more unique and meaningful bonds you can create through digital friendships.

Azar provides a casual space to ignite fun and lighthearted conversations via one-to-one video chat. So, join the platform, try out these conversation starters and watch new connections grow into something unique and special.

Start Chatting now!