How to Keep A Conversation Going? | Complete Guide

In a world of rapid-fire texts and fleeting chats, mastering the art of conversation remains a timeless skill.

Whether you’re closing a deal in sales, building friendships, or navigating dating apps, knowing how to keep a conversation going can transform awkward silence into meaningful connection.

This guide reveals proven techniques to keep conversations flowing naturally, both over text and face-to-face, so you can build rapport, network effectively, and leave a lasting impression.

So, let’s get started.

Why conversation matters in sales?

Great conversations aren’t just pleasant, they’re essential for success in sales, networking, and personal relationships.

Here’s why:

• Know customer needs: Genuine dialogue helps you understand pain points and tailor your pitch accordingly, rather than delivering a one-size-fits-all solution.
• Build trust: When you show you care about someone’s situation (not just closing a deal or filling silence), you create authentic connections that last beyond a single interaction.
• Present value: By listening actively, you can position your product, service, or ideas as the perfect solution to the specific challenges they’ve mentioned.
• Close effectively: Conversations reveal buying signals, hesitations, and opportunities to address objections, turning prospects into customers and acquaintances into friends.

In short, good conversation builds trust, reveals needs, and lets you present solutions that resonate with the customer.

Now comes the real question.

What makes a good conversation?

A good conversation requires give-and-take, connection, and a willingness to move with the flow. Here are some key elements that make it all come together:

• Active listening: This is more than just waiting for your turn to talk. It’s about truly paying attention, asking clarifying questions, and showing genuine interest in what the other person is saying.
  
• Balance: A good conversation is a two-way street. There should be a balance between speaking and listening, ensuring both participants feel heard and valued.
  
• Engagement: Great conversations are sparked by curiosity and a desire to learn more. Ask open-ended questions that go beyond yes/no answers, and share your own thoughts and experiences in a relatable way.
  
• Mutual respect: It’s about creating a safe space where everyone feels comfortable expressing themselves, even if there are disagreements. Be open-minded and acknowledge different perspectives.
  
• Flow: Conversations that flow naturally are a joy. Pick up on cues and build on what the other person is saying. If the topic shifts organically, be flexible and go with it.
  
• Energy: Enthusiasm is contagious! Show genuine interest in the conversation, and your partner will likely reciprocate, creating a positive and engaging dynamic.

• Active intention: If your intention sucks, people will not bother keeping any conversation going with you.
  

Overall, a good conversation isn’t just about exchanging information, it’s about building connections and fostering a sense of enjoyment. By incorporating these elements, you can turn any conversation into a delightful exchange.

Recommended Read: 170 Professional Conversation Starters For  Every Situation

15 proven ways to keep a conversation going

Facing someone new and striking up a conversation can feel daunting, but it’s a skill that gets easier with practice. The key is to keep things flowing and engaging for both of you. 

Here are some tips to turn those initial jitters into a smooth and enjoyable conversation. They can be used for both online and offline conversations. 

#1 Ask open-Ended Question

Instead of “Did you enjoy the movie?”

Try “What specifically resonated with you in the movie?”. This invites them to elaborate on their favorite scenes, characters, or themes.

Instead of “The weather is crazy, right?” try “Why do you think this heatwave is so intense?”. This sparks discussion about climate change, summer plans, or even funny anecdotes about dealing with the heat.

#2 Practice active listening 

Hear them out, then say something like “So you’re saying you finally mastered that baking recipe? That’s fantastic! I’ve been wanting to try it myself, any tips?”. This shows you were paying attention and opens the door for further conversation.

If something is not clear, ask open-ended questions that show interest. “You mentioned this new hiking trail being challenging; what made it difficult?”. This demonstrates you’re engaged and want to understand their experience.

#3 Finding common ground

Notice details in their clothing, accessories, or comments. “Hey, that’s a cool [band T-shirt]! I love them too, what’s your favorite album?”. This creates a quick connection based on shared taste.

“We both mentioned loving Italian food,” you say, “Have you tried that new restaurant downtown everyone’s raving about?”. This builds on a common interest and opens the door to discussing new experiences.

#4 Turning comments into conversation 

Instead of “Oh, that’s cool” when they mention their trip to France, say “Wow, France is amazing! What city did you visit? Did you try any traditional pastries?”. This shows genuine interest and keeps the conversation flowing.

If they mention disliking a recent movie, ask “What specifically didn’t work for you in the plot?”. This sparks a deeper discussion about movie preferences and genres.

#5 Sharing like a conversation 

They mentioned a love for rock climbing, so you respond “That’s interesting! I used to do indoor rock climbing a while back, it’s a great workout. What kind of climbs do you enjoy the most?”. Sharing a relevant anecdote keeps the exchange balanced.

#6 Piggybacking on their passion

They mention rock climbing, so ask “What got you into rock climbing in the first place? Is it the challenge or the sense of accomplishment?”. This shows curiosity about their specific interest and can lead to a more engaging conversation.

#7 Segueing Smoothly

Let’s say they talk about their love for rock climbing gyms. You can say “That climbing gym sounds like a great community space. Do you enjoy going to concerts too? There’s a cool band playing at a local venue next week…”. This smoothly transitions to a related topic while keeping the conversation going.

#8 Acknowledge awkward silence with humor

A lighthearted touch can bridge the gap. “Sometimes these conversations take unexpected turns; that’s okay, right? Maybe we can circle back to that later?”. This acknowledges the silence and assures them it’s not a big deal.

If the silence persists, ask a general, open-ended question like “What are you looking forward to this summer?” or “Have you tried any new restaurants lately?” This provides a safe conversational springboard.

#9 Use positive body language

This projects warmth, confidence, and genuine interest in what they’re saying.

Subtle movements show you’re engaged and actively listening, encouraging them to elaborate.

#10 Ask for elaboration

Go beyond simple agreements. Instead of a bland “Oh cool,” when they mention their trip to France, delve deeper: “France is amazing! What city did you visit? Did you try any traditional pastries?” These open-ended questions show genuine interest and encourage them to elaborate on their experiences.

#11 Do your homework

A little preparation can go a long way. If you know you’ll be meeting someone new, try to find some common ground beforehand. Did they mention a love for rock climbing on social media? Look up interesting facts about climbing or popular climbing gyms in your area. This equips you with conversation starters and shows you took an interest in their world. You can check out “conversation starter” blog for more information. 

#12 Tell a story

Conversations are a two-way street. They mentioned a love for rock climbing, so share a relevant anecdote: “That’s interesting! I used to do indoor rock climbing a while back, it’s a great workout. What kind of climbs do you enjoy the most?” Sharing a personal story keeps the exchange balanced and shows you’re an active participant.

#13 Give & ask for recommendations

People love sharing their passions! If they rave about a new restaurant, ask for their recommendation: “Wow, that new restaurant downtown sounds delicious! What dish did you enjoy the most?”. Reciprocate by offering a recommendation of your own: “Have you tried [recommended restaurant]? Their [recommended dish] is fantastic.” This exchange fosters a sense of connection and keeps the conversation flowing.

#14 Project confidence and positivity

Confidence is attractive! Smile, make eye contact, and speak clearly. This projects warmth, approachability, and genuine interest in what they’re saying. People gravitate towards those who exude positive energy.

#15 Be prepared with icebreakers

A little preparation can ease the pressure, especially if you’re meeting someone new. Have a few conversation starters in your back pocket – a funny observation about the current situation, a thought-provoking question, or a lighthearted comment about something in your surroundings. This gets the ball rolling and creates a comfortable space for conversation to unfold.

How to keep online conversations going?

Online conversations, whether over text messages, social media DMs, or dating apps, require some special attention to keep them flowing. Here are a variety of ways to ensure your online chats stay engaging:

#1 Engaging question

Ditch “What’s up?”: Instead, use engaging prompts like “What’s been the highlight of your week?” or “What are you passionate about lately?”

Use “Why” and “How”: Transform statements into discussions. “That new song is catchy!” becomes “Why do you love that new song? What about it resonates with you?”

Ask about their day meaningfully: Rather than “How was your day?”, try “What’s one thing that made you smile today?” or “Any wins you want to celebrate?”

#2 Active listening

Don’t just react: Avoid lazy responses like 👍 after their message. Summarize what they said and add thoughts: “You mentioned missing your friends, that must be tough. Are there any virtual hangouts planned?”

Ask clarifying questions: “You mentioned a new project at work, sounds exciting! What kind of project is it?”

Reference previous conversations: “Last week you mentioned wanting to try that new restaurant. Did you end up going?”

#3 Finding common ground in online chats

Look for profile clues: Notice details in their profile picture, bio, or messages. “Hey, that’s a cool picture from [Location]! I’ve always wanted to visit there.”

Expand on shared interests: “We both love that same band. Have you listened to their new album yet? I’m obsessed with the second track.”

Use conversation history: Refer back to topics you’ve discussed before to show you remember and care.

#4 Turn comments into conversation starters over text

Expand, don’t just agree: Instead of “Cool!” when they mention a new hobby, say: “That’s interesting! I’ve always been curious about [hobby]. What got you into it?”

Ask for details: If they mention disliking a movie, ask “What specifically didn’t work for you in the plot?” to spark deeper discussion.

Build on their energy: If they’re excited about something, match their enthusiasm: “That sounds amazing! Tell me more!”

#5 Sharing is caring

Keep it balanced: They mentioned cooking, you respond: “I love to cook too! What’s your favorite dish to make? I’ve been perfecting my pasta carbonara lately.”

Don’t make it about you: Share relevant experiences, but always circle back with a question to keep the focus balanced.

#6 Embrace the GIF or meme

When to use them:

• To add humor and lighten the mood
• When words feel inadequate
• To show you “get” their sense of humor

When to avoid:

• As a substitute for real conversation
• Overusing them (makes you seem lazy)
• Sending anything overly generic or impersonal

The rule: Use visuals as seasoning, not the main dish.

#7 Gently address awkward silences

Acknowledge it lightly: “Sometimes these online chats take unexpected turns, that’s totally okay, right? 😊”

Suggest a fun activity: If the silence persists, propose a quick game: “Want to play ‘Two Truths and a Lie’? I’ll start!” or “Have you seen this hilarious video I came across?”

Pivot to a new topic: “Random question: if you could travel anywhere next month, where would you go?”

#8 Keep it positive and upbeat

People gravitate toward positive energy, even in text form.

Things to say that keep conversations light:

• “That sounds like so much fun!”
• “I love your perspective on this”
• “You’re so right about that”
• “This conversation is making my day”

Avoid:

• Excessive complaining or negativity
• Rants (save for close friends who know you well)
• Passive-aggressive comments

Why it matters: Upbeat conversations make people want to keep texting you.

#9 Respond in a timely manner

The sweet spot: Respond within a few hours (or sooner if the conversation is flowing). No one likes being left on read for days.

Balance responsiveness: Don’t be so fast you seem desperate, but don’t wait so long you kill momentum.

Be honest if you’re busy: “Hey! Super busy right now but wanted to say this sounds great, can we continue this tonight?”

Things to say to keep a conversation going

Sometimes you need specific phrases ready to deploy when conversations start to stall. Here are proven things to say in various situations:

When meeting someone new:

“What brought you here today?”
“That’s really interesting, tell me more about that.”
“How did you get into [their field/hobby]?”
“What’s been keeping you busy lately?”
“I’d love to hear your perspective on this.”

When conversation lulls:

• “Random question: if you could have dinner with anyone dead or alive, who would it be?”
• “What’s something you’re really looking forward to?”
• “Have you discovered any great [books/podcasts/shows] lately?”
• “What’s the most interesting thing you’ve learned recently?”

Over text when they give short answers:

• “That’s cool! What made you interested in that?”
• “I’m curious, how does that work exactly?”
• “Sounds like there’s a story behind that…”
• “What do you love most about it?”

In sales conversations:

• “What challenges are you currently facing with [problem area]?”
• “How are you handling [specific issue] right now?”
• “What would your ideal solution look like?”
• “Can you walk me through your current process?”

To show you’re listening:

• “That makes total sense because…”
• “So if I understand correctly, you’re saying…”
• “I can see why you’d feel that way.”
• “That reminds me of what you mentioned earlier about…”

Pro tip: Adapt these phrases to match your natural speaking style. Authenticity matters more than perfect wording.

Benefits of having an ongoing communication

Ongoing communication offers a wealth of benefits, both in personal and professional settings. Here’s a breakdown of some key advantages:

Stronger relationships: Regular conversations build closeness, trust, and help prevent misunderstandings. Whether you’re nurturing friendships or client relationships, consistent communication deepens bonds.

Enhanced teamwork: In business settings, ongoing dialogue keeps everyone aligned, boosts team morale, and enables faster problem-solving. Tools like SmartReach help maintain consistent touchpoints with prospects and customers.

Continuous learning: Exchanging ideas and feedback fosters personal growth, keeps you informed about industry trends, and opens doors to new opportunities.

Improved well-being: Open communication reduces stress, combats isolation, and strengthens your support system, crucial for both mental health and professional resilience.

Enhanced Creativity: Open communication fosters an environment where brainstorming can thrive, enabling the exchange of diverse perspectives. This dynamic interaction often sparks innovative ideas, much like how Canva’s Drawing App can serve as a versatile tool for visualizing and refining those concepts.

Conflict prevention: Addressing concerns early through ongoing dialogue prevents small issues from escalating into major problems that damage relationships.

Recommended Read: A Complete Guide to Small Talk: Conversation Starter, Meaningful Engagement, and More

Take away: How to keep conversation going?

Conversation is very important in sales, and in many other parts of life too! Just talking at someone isn’t enough. You need to have a back-and-forth conversation to really understand their needs and build a connection. This will help you close the deal and build lasting relationships.

For any conversation:

• Ask open-ended questions that invite elaboration
• Listen actively and show genuine interest
• Find common ground to build quick connections
• Share relevant stories to create balance
• Stay positive and confident

Specifically for text conversations:

• Use engaging questions instead of “What’s up?”
• Respond thoughtfully, not just with emojis
• Reference previous conversations to show you remember
• Keep the energy positive and upbeat
• Reply within a reasonable timeframe

But good conversation skills are important everywhere, not just in sales. Whether you’re chatting with friends online or making new acquaintances, keeping the conversation flowing is key. By following these tips, you can become a conversation pro and connect with anyone!

Here’s an extra tip: Remember, body language is important too! Smile, make eye contact, and listen attentively. This shows the other person you’re interested in what they have to say. With a little practice, you’ll be conversing with confidence in no time!

Frequently Asked Questions (FAQs)

How to keep a conversation going over text?

Ask open-ended questions that invite detailed responses rather than yes/no answers. Practice active listening by responding thoughtfully to their messages and asking follow-up questions that show genuine interest. Look for common interests in their profile or previous conversations to find natural discussion topics.

I always run out of things to say in conversations. Help!

Ask open-ended questions and actively listen to their responses. Find common ground through shared interests. Share your own relevant stories and experiences. Keep conversation starters ready for new situations. Remember: curiosity and genuine interest matter more than having perfect things to say every time.

How can I make online conversations more engaging?

Use engaging prompts instead of predictable questions. Respond thoughtfully with follow-up questions that show interest. Notice details in their profiles to identify shared interests. Use GIFs or memes sparingly to add humor. Most importantly, reply in a timely manner and keep your messages positive and upbeat.

What are the benefits of good communication skills?

Strong communication builds trust and deepens relationships in all areas of life. It improves teamwork, enhances problem-solving abilities, and boosts creativity. Open dialogue reduces stress, prevents conflicts, and improves overall well-being. Effective communication skills are essential for career success and maintaining healthy personal relationships.

What are some things to say when conversation stalls?

Try: “What are you looking forward to?” or “Have you discovered anything interesting lately?” Ask about their passions: “What got you into that?” Reference shared interests: “Have you tried that restaurant we mentioned?” In sales: “What challenges are you facing with [problem]?” Keep questions open-ended and show genuine curiosity.

How do I keep a conversation going on dating apps?

Ask about interests mentioned in their profile rather than generic openers. Use “why” and “how” questions to encourage detailed responses. Share relevant experiences but always circle back with questions. Respond meaningfully beyond simple emoji reactions. Suggest moving to a phone call if texting feels stale.

How can I improve my conversation skills quickly?

Practice active listening by fully focusing on what others say. Prepare open-ended questions beforehand. Find common ground through shared interests. Share relevant personal stories. Project confidence through body language and tone. Most importantly, be genuinely curious about others, authentic interest is the foundation of great conversations.

What should I avoid in conversations?

Avoid dominating the conversation or making everything about yourself. Don’t ask only yes/no questions. Avoid excessive negativity or complaining. Don’t interrupt or stop listening to plan your next response. Skip controversial topics in early conversations. Avoid checking your phone constantly. Don’t give one-word responses in text conversations.