“Conversation” is a form of communication where two or more people exchange ideas, thoughts, questions, or feelings—usually in a spoken format, though it can also happen in writing (like we’re doing now).
At its core, a conversation is:
Interactive – people take turns talking and listening.
Responsive – what one person says usually influences what the other says.
Natural – it flows without being rigid or scripted (unless it’s a formal interview or something).
Purposeful – it can be casual, informative, persuasive, comforting, or just for fun.
So basically, anytime you’re genuinely engaging with someone and there’s back-and-forth communication, you’re in a conversation.
WHEN SOMEONE SAYS THEY “CAN’T CARRY ON” OR “CAN’T HOLD A CONVERSATION,” THEY USUALLY MEAN THEY STRUGGLE TO KEEP A CONVERSATION GOING NATURALLY OR COMFORTABLY. HERE’S WHAT THAT CAN LOOK LIKE:
It might mean:
They don’t know what to say next.
Like after the small talk, they run out of things to say and there’s an awkward silence.
They feel nervous or shy.
Social anxiety can make someone feel frozen or self-conscious about what to say or how they’ll be perceived.
They have trouble listening or responding well.
Conversations are two-way, so if someone isn’t good at listening or reacting thoughtfully, the flow can break down.
They overthink or get stuck.
Some people worry too much about saying the “right” thing, which makes it hard to relax and just talk.
They don’t know how to connect with the other person.
Finding common interests or reading social cues can be tricky, especially for people who haven’t had a lot of social experience or have conditions like autism.
Example:
Imagine someone is talking to a coworker and they say:
“So, did you do anything over the weekend?”
The other person replies, “Nah, not really.”
Now what? If the first person doesn’t know how to respond or keep things going (like asking a follow-up or switching topics), the conversation fizzles.
IF SOMEONE STRUGGLES TO HOLD A CONVERSATION, THERE ARE SOME CLEAR SIGNS THAT CAN SHOW IT. HERE ARE THE TOP ONES:
One-word or very short answers
They might respond with just “yeah,” “no,” or “I guess,” without adding anything extra or asking a follow-up. It makes the conversation hard to keep going.
Flat or awkward body language
They may avoid eye contact, seem very stiff, or distracted, and show no facial expression. It can give the impression they aren’t engaged.
They don’t ask questions back
A conversation should go both ways. If someone answers your question but never asks one in return, it becomes one-sided and usually dies out.
Constantly changing the subject
Instead of sticking to one topic and exploring it, they jump around randomly, making the conversation feel disjointed or confusing.
Frequent awkward silences
Some silence is normal, but if there are a lot of long, uncomfortable pauses, it can signal someone doesn’t know how to keep the talk going.
They seem very nervous or uncomfortable
You might notice them fidgeting, speaking in a rushed or hesitant way, or looking unsure of themselves. This nervous energy can make conversation harder.
Talking too much or too little
Some people dominate the conversation and never let others speak, while others barely talk at all. Either extreme can make conversation difficult.
Closed-off behavior
Crossed arms, facing away, or giving short, distant replies can signal disinterest or discomfort, which makes it hard to connect.
Not all of these signs mean someone is rude — often they’re just shy, inexperienced, or anxious. But these patterns can definitely make conversation tough.
BEING ABLE TO HOLD OR CARRY A CONVERSATION CAN HELP YOU IN LIFE IN A LOT OF POWERFUL WAYS—BOTH PERSONALLY AND PROFESSIONALLY. HERE’S HOW:
Builds Better Relationships
Whether it’s friends, family, coworkers, or strangers, conversation is the foundation of connection. If you can hold a conversation, you’re more likely to:
Make new friends
Keep relationships strong
Understand others better
Boosts Confidence
When you’re comfortable talking with people, you’re less nervous in social situations—whether it’s a date, a meeting, or a party. That confidence can show in your posture, your tone, and the way others respond to you.
Opens Up Opportunities
A good conversation can lead to:
Job offers
Mentorships
Business partnerships
Learning new things You never know who you’re talking to or what might come from a simple chat.
Improves Problem-Solving
Being able to talk through a situation—clearly and calmly—can help you resolve misunderstandings or conflicts. It also helps you ask better questions, get clearer answers, and find solutions faster.
Makes You More Likeable
People naturally enjoy being around someone who listens well, asks good questions, and keeps the conversation going smoothly. It makes you seem thoughtful, easy to talk to, and interesting.
Helps You Learn
Conversations expose you to new ideas, different perspectives, and life experiences you might not get on your own. It’s a two-way street of learning.
Leads to Stronger First Impressions
Whether you’re meeting someone for the first time socially or professionally, being able to carry a conversation leaves a strong, positive impression. That can be important in interviews, networking, or even meeting a future partner.
A PERSON WHO CAN HOLD OR CARRY ON CONVERSATIONS WELL OFTEN HAS A MIX OF PERSONALITY TRAITS AND PRACTICAL HABITS THAT MAKE THEM EASY TO TALK TO AND ENJOYABLE TO BE AROUND. HERE ARE SOME OF THE TOP TRAITS:
Good Listener
They don’t just wait for their turn to talk—they really pay attention to what you’re saying. They make you feel heard and understood, which keeps conversations going naturally.
Curious
They ask questions and show genuine interest in others. Their curiosity helps draw people out and makes others feel like their thoughts or experiences matter.
Empathetic
They can sense how others are feeling and respond with understanding. This helps them stay in tune with the tone of the conversation and respond appropriately.
Confident (but not overbearing)
They’re comfortable speaking up, but they don’t dominate the conversation. They balance talking and listening well.
Positive Attitude
They keep the energy light and encouraging, even when the topic is serious. People tend to enjoy talking with someone who lifts the mood instead of bringing it down.
Observant
They notice details in what others say and can follow up naturally. For example, if you mention a hobby, they might ask a question about it later—showing they were paying attention.
Adaptable
They know how to switch gears if a topic isn’t working, adjust their tone for the setting, and keep things appropriate for the moment.
Clear Communicator
They speak clearly and stay on topic without rambling. They also know how to explain things in a way that others can follow.
Open-minded
They don’t judge quickly or shut people down. Instead, they let others speak and are open to new ideas or experiences.
Good Sense of Timing
They know when to talk, when to pause, and when to let the other person have the floor. This sense of rhythm helps keep things smooth.
IF YOU’RE DOING EVERYTHING RIGHT—LISTENING WELL, BEING CURIOUS, KEEPING THE TONE FRIENDLY—AND THE OTHER PERSON STILL GIVES SHORT ANSWERS, HERE ARE A FEW POSSIBILITIES AND WAYS TO HANDLE THEM:
They Might Be Shy or Socially Anxious
Some people genuinely struggle to open up. Short answers could mean they’re nervous, unsure of themselves, or don’t know what to say.
What to do:
Keep the pressure low. Ask easy, open-ended questions (like “What was that like for you?” or “How did you get into that?”). Also, share a little more of yourself—sometimes people open up when they feel it’s safe or when someone else goes first.
They May Not Be in the Mood to Talk
People get tired, distracted, or preoccupied. If they’re mentally somewhere else, even a great conversation partner can’t pull much from them.
What to do:
Pay attention to body language and tone. If they seem checked out, it’s okay to let the conversation rest. You can always say, “You seem like you’ve got a lot on your mind—want to catch up another time?”
They Might Not Be Interested in the Topic
Short answers can also signal boredom—not with you personally, but with the subject at hand.
What to do:
Try gently shifting the topic. You might say, “Totally fine if that’s not your thing—what kind of stuff do you like talking about?” This gives them a chance to steer the conversation.
They May Not Want to Talk to You
Sometimes, for whatever reason—chemistry, assumptions, mood—they just don’t feel like engaging. It’s not always personal, but it can feel that way.
What to do:
If you’ve made a sincere effort and they’re still cold or dismissive, it’s okay to respectfully disengage. Not everyone will be receptive, and that’s not a reflection on your effort or character.
They Might Be Testing the Waters
Some people take a little longer to warm up. They start with short answers to feel things out before engaging more.
What to do:
Be patient. Keep things light and low-pressure. Sometimes just a little time and trust is all it takes.
Holding a conversation is a two-way street—but not every street has smooth traffic. You’re doing your part by showing the right qualities. If the connection doesn’t click, that’s okay—it happens to everyone.
Here are several deeper thoughts about holding or carrying on a conversation—things that go beyond the basics and may help you become not just a good conversationalist, but a memorable one.
Conversation is not just words—it’s presence.
One of the most overlooked parts of a good conversation is being fully present. It’s easy to fall into the habit of thinking about what you’re going to say next, checking your phone, or mentally drifting.
But when someone feels like they have your full attention, it creates a deeper sense of trust and connection. Being present can sometimes mean simply listening without interrupting or holding a few seconds of eye contact as someone speaks. These moments build a kind of silent respect that words alone can’t.
Matching energy is a powerful tool.
People tend to feel more comfortable with those who subtly match their tone, pace, and energy level. This doesn’t mean copying them, but if someone is laid-back and you come in loud and intense, it might throw things off.
Likewise, if someone’s excited about something, responding with equal enthusiasm keeps the spark alive. Being able to mirror someone’s energy without losing your authenticity is one of the most natural ways to keep a conversation flowing.
Stories make people lean in.
Facts are helpful, but stories make conversations stick. People remember how you made them feel, and nothing delivers emotion quite like a short, meaningful story. You don’t have to be dramatic or overly detailed.
Even small personal stories—a funny moment, an awkward situation, a lesson learned—can create relatable and warm exchanges. The more real and human your stories are, the more people feel connected to you.
Vulnerability invites depth.
When you’re willing to let down your guard a little—by admitting you don’t know something, sharing a challenge you’ve faced, or expressing a genuine opinion—it makes space for the other person to do the same. Conversations often deepen when someone takes the first step to be a bit real. Of course, timing matters, and it doesn’t mean oversharing. But a little vulnerability goes a long way toward making the exchange meaningful rather than just surface-level.
Silence doesn’t always mean failure.
Many people panic when a conversation hits a pause. But silence isn’t always bad—it gives room for thought, processing, or just a natural break. In fact, comfortable silence between people can be a sign of trust.
If a moment of quiet comes up, there’s no need to rush to fill it. A thoughtful question or even a relaxed comment like “That’s something I hadn’t thought about before” can turn the pause into a doorway to something deeper.
Being able to carry a conversation well isn’t just about talking—it’s about connection. When you treat it as an opportunity to understand, uplift, or simply enjoy the company of another person, you start to move past technique and into meaning. And that’s where the real magic happens.
Here’s a list of good questions and conversation starters that work in many situations—whether you’re getting to know someone, reconnecting, or keeping things rolling. These can be adapted to fit casual, deep, or even professional conversations depending on your tone and setting.
🔹 General Starters (Friendly and Easygoing)
- “So what’s been the highlight of your week so far?”
- “How do you usually spend your weekends?”
- “Have you tried anything new lately—food, activity, show, anything?”
- “What’s something you’re into that not many people know about?”
🔹 Interest-Based (Great for Finding Common Ground)
- “Do you have any hobbies you’re passionate about?”
- “What kind of music/movies/shows do you never get tired of?”
- “Are you more of an outdoor or indoor type?”
- “If you had an entire day to yourself, what would you do with it?”
🔹 Deeper but Not Too Intense (Invites Meaningful Talk)
- “What’s something you’ve learned recently that surprised you?”
- “Is there a goal or dream you’ve had for a while?”
- “What’s something small that always makes your day better?”
- “Have you ever had an experience that really changed how you think?”
🔹 Light and Fun (Breaks the Ice or Shifts Energy)
- “If you could instantly master one skill, what would it be?”
- “Would you rather explore space or the deep ocean?”
- “What’s the most random or funny thing you’ve seen lately?”
- “If someone made a movie about your life, what kind of movie would it be?”
🔹 Work/School Conversations (Without Feeling Dry)
- “What got you interested in the work/study you’re doing now?”
- “What’s something about your job (or field) that most people don’t understand?”
- “If you could do any project just for fun, what would it be?”
- “Do you like what you do, or are you more in it for the paycheck?”
🔹 Universal Fallbacks (Almost Always Work)
- “Been on any trips lately or planning to go anywhere soon?”
- “What’s the best thing you’ve eaten recently?”
- “Are you more of a morning person or night owl?”
- “What’s something that always relaxes you?”
Bonus Tip:
React, don’t just ask. When they answer, respond with curiosity, follow-up questions, or a story of your own. That’s what turns a series of questions into a real conversation.
Here’s a more organized breakdown of good conversation questions and starters, grouped by the type of person or situation you’re likely to be in. These are all designed to feel natural and not forced, depending on the vibe you’re going for.
For First Conversations or Casual Acquaintances
These help break the ice and get people talking in a relaxed way.
What kind of things do you enjoy doing in your free time?
Have you always lived around here?
Tried anything new or different lately?
If you could visit anywhere in the world, where would you go?
Do you have any favorite local spots—coffee, food, places to relax?
For Getting to Know Someone Better (Friendship or Early Dating)
These add a bit of depth and help uncover common interests or values.
What kind of stuff really gets you excited or inspired?
Do you have any goals you’re working toward right now?
What’s something small that makes a big difference in your day?
What kinds of things do you value most in your close friends?
Do you ever think about what you’d do if money didn’t matter?
For Talking to Coworkers or Professional Contacts
These keep things friendly, appropriate, and engaging in a workplace or networking setting.
How did you end up working in your current field?
What’s the most rewarding part of your job?
Have you had any mentors or people who really influenced your path?
If you weren’t doing this kind of work, what else would you try?
How do you usually unwind after a busy week?
For Hanging Out with Old Friends or Reconnecting
These help you pick up where you left off, go deeper, or just have a good time.
What’s something that’s changed about you in the last year or so?
Have you picked up any random hobbies or new interests?
What’s one of your favorite memories from the time we’ve known each other?
What’s something funny or strange that’s happened to you lately?
If you could relive a day or moment from the past, what would it be?
For Small Talk or Random Conversations (Line at the store, event, etc.)
These are light and safe for just about anyone.
Busy day or taking it easy today?
Weather’s been wild lately—do you usually like this kind of season?
Do you come here often or just checking it out?
What kind of music or shows have you been into recently?
Are you more of a morning person or a night owl?
BEING ABLE TO HOLD OR CARRY ON A CONVERSATION CAN DEFINITELY MAKE YOU MORE TRUSTWORTHY AND LIKABLE. HERE’S WHY:
Demonstrates Empathy and Interest
When you actively engage in a conversation and show genuine interest in others’ thoughts and feelings, it signals that you value them. People tend to like and trust those who show empathy, listen carefully, and respond thoughtfully. A person who can carry on a conversation without dominating it or making it all about themselves comes across as more caring and emotionally intelligent.
Builds Rapport and Connection
Good conversations create a sense of rapport. When you can connect on shared experiences, values, or even humor, it strengthens bonds and makes you more likable. Trust often stems from feeling like someone understands you and is easy to talk to. If you can share personal stories, ask thoughtful questions, and show interest in what others have to say, people are more likely to feel comfortable and trust you.
Signals Confidence, Not Arrogance
Being able to hold a conversation well usually indicates a level of social confidence. People gravitate toward individuals who are confident enough to speak their mind, yet humble enough to listen and acknowledge others. However, it’s important to balance confidence with humility. Someone who can talk, listen, and engage without coming across as self-absorbed is more likely to be seen as trustworthy and approachable.
Shows Respect and Awareness
A person who can sustain a conversation without interrupting or dominating the discussion shows respect for others’ perspectives. This awareness makes others feel safe in expressing themselves, which fosters trust. When you communicate with respect and mindfulness, people are more likely to trust you with personal thoughts and feelings.
Creates Comfort and Reduces Tension
When you can carry a conversation naturally, it helps put people at ease, especially in new or awkward situations. Someone who can navigate conversations smoothly is seen as socially adept, which leads people to feel more comfortable around them. When people feel comfortable, they’re more likely to like and trust you.
In short, being a good conversationalist helps you build trust by making people feel heard, respected, and valued. It also makes you more likable because you’re engaging, approachable, and able to create a connection with others.
Being able to hold or carry on a conversation is more than just a social skill—it’s a vital part of connecting with others and building trust. It’s not about saying the right things all the time, but rather about being present, showing interest, and creating an environment where others feel comfortable and heard.
The more you engage thoughtfully, listen actively, and share appropriately, the more natural and meaningful your interactions will become. It’s these small, yet powerful, exchanges that lay the foundation for strong relationships, whether in personal or professional settings.
The ability to carry a conversation doesn’t just make you more likable; it helps you understand others better, strengthens your own communication skills, and builds a sense of connection that makes people want to be around you. It’s a give-and-take process that involves not only talking but also listening, asking insightful questions, and being mindful of the moment.
As with any skill, practicing your conversational abilities will make you even more comfortable in social situations. And remember, the goal isn’t to impress others with what you know, but to engage in meaningful dialogue that fosters understanding, trust, and mutual respect. Whether you’re meeting someone new, maintaining friendships, or navigating professional environments, your ability to converse well will serve you in countless ways, helping you to build connections that last.
IF YOU’RE LOOKING FOR MORE INFORMATION ON THE ART OF CONVERSATION AND HOW TO IMPROVE YOUR SKILLS, THERE ARE SEVERAL RESOURCES ACROSS DIFFERENT FORMATS THAT CAN HELP DEEPEN YOUR UNDERSTANDING AND REFINE YOUR ABILITIES. HERE ARE A FEW OPTIONS:
Books:
- “How to Win Friends and Influence People” by Dale Carnegie
- A classic that teaches communication and relationship-building skills. It covers everything from small talk to building lasting connections with others.
- “The Fine Art of Small Talk” by Debra Fine
- This book focuses specifically on mastering small talk and turning casual conversations into meaningful interactions.
- “Conversationally Speaking” by Alan Garner
- A practical guide to improving your conversation skills with tips on how to be an engaging, thoughtful speaker.
- “The Charisma Myth” by Olivia Fox Cabane
- While focusing on charisma, this book offers great insights on how to be more engaging and likable in any conversation.
Podcasts and Videos:
- The Art of Charm Podcast
- Focuses on improving social skills, building rapport, and navigating conversations in a way that builds trust and influence.
- TED Talks
- Talks on communication, public speaking, and emotional intelligence can deepen your understanding of effective conversations. Speakers like Julian Treasure (“How to Speak So That People Want to Listen”) have great insights on communication.
- The School of Life YouTube Channel
- Offers videos on improving relationships, communication, and understanding human behavior, all of which can help in conversations.
Online Courses:
- Udemy and Coursera
- These platforms have numerous courses on improving communication skills, mastering conversation, and emotional intelligence. Look for courses like “Mastering Conversation” or “Effective Communication.”
- LinkedIn Learning
- Offers professional courses on conversational skills, networking, and emotional intelligence.
Websites and Articles:
- Psychology Today
- Articles on emotional intelligence, communication skills, and social dynamics can provide expert advice on holding better conversations.
- Verywell Mind
- Provides accessible articles on communication, building rapport, and strengthening social connections.
- Harvard Business Review
- Articles and resources on professional communication and improving interpersonal skills in business environments.
Social Groups and Workshops:
- Toastmasters International
- A global organization that helps people improve their public speaking and leadership skills. It’s a great way to practice holding conversations in a supportive, structured environment.
- Meetup Groups
- Look for local or online groups focused on improving communication or networking skills. These gatherings can provide both practice and feedback.
These resources should give you a wide range of perspectives and techniques to enhance your conversational skills.