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45 Happy Ways to Keep a Conversation Going and Be a Lot of Fun to Talk To

Knowing how to keep a conversation going is a good skill to have. Not only can you talk to anyone, but people will find you super-interesting! 

how to keep a conversation going

Everyone loves talking and sharing their ideas. More than that, we want to become wonderful conversationalists so everyone will love hanging out with us. If you’re wondering how to keep a conversation going with anyone, maybe you’re focusing on the wrong thing.

When we think of things to talk about with someone, our mind goes into overdrive, looking for conversation topics. 

But what if that’s the wrong way to go looking for things to talk about? What if there’s an easier and far more relaxed way to talk to anyone and keep the conversation going for as long as you’d like? [Read: 35 best text conversation starters for the shy and socially awkward]

The bad conversationalist and the good one

A good conversationalist isn’t someone who just knows how to speak well. This is a mistake many people make. They assume that anyone who can talk can instantly hold a conversation together. And yet, sometimes, a quiet listener can be called a wonderful conversationalist, too!

If you fall in love with your own voice and can’t stop talking because you’re “so good at it,” it makes you a conversational narcissist rather than a good communicator!

The next time you’re in a passionate discussion with someone and feel like a real winner because they gave up on the conversation, don’t assume that you’re great at holding the conversation. In fact, it’s moments like these that make people bad conversationalists.

Learn to listen! [Read: Are you a conversational narcissist who loves talking and hates listening?]

The first few minutes of a new conversation

For most of us, the first few minutes of a new conversation are the absolute worst. It’s awkward, uneasy, and an almost toe-curling nightmare.

You don’t know what to say. They’re staring at you blankly because they don’t know what to say. Both of you smile awkwardly and look around, hoping someone else will pop in and save you both from this nightmare.

But what if you could be that person who saves the day and the conversation? Can you become the person everyone instantly feels relaxed around because they know you’ll say all the right things and turn an awkward moment into something fun and easy?

Here’s something to remember. As annoying as those first few minutes are, it is those very few minutes that will turn out to be the biggest judge of your conversation skills. After all, first impressions are made from first conversations. [Read: 19 ways to be a much better listener in a relationship and read their mind]

How to make the first few minutes work in your favor

If you can ensure that the first few minutes are exciting and fun, they’ll look forward to sticking around for the whole evening.

When it comes to the first few minutes, here are all the things that matter most. [Read: How to make people like you – 35 tips to charm absolutely anyone]

1. Appear confident

Have an upright and confident posture and stand tall. If you want to catch someone’s eye or get them to engage in a conversation with you, you have to intrigue them. After all, you picked someone to talk to because you found them interesting.

Why would someone want to get into a conversation with you if they don’t think you’re interesting? If you want to get them interested in you, you need to appear interesting. [Read: How to introduce yourself – the art of making a great first impression]

2. Appear relaxed

Your energy is contagious. Have you ever felt anxious while standing next to someone who seemed nervous, flustered, and all over the place? If you feel relaxed, they will, too! When you’re standing next to someone, don’t fidget. Take a few deep breaths. Pretend like you’re enjoying every single thing around you, and you will!

3. Your first smile

Flash a quick and warm smile at the person you’re talking to. It almost instantly makes anyone feel at ease. If you haven’t started talking yet, you can nod, smile, and look away for a moment.

If you’ve been introduced, smile warmly and just look at them with mild curiosity. You don’t have to say something immediately. Sometimes, just smiling and looking at them will make the other person initiate the conversation! [Read: How to make a good first impression and impress everyone you meet]

4. Don’t be nervous about looking around

When you want to keep a conversation going, you don’t have to stare intently at the person you’re talking to. Sometimes, it’s far more comfortable to take a second and scan your eyes curiously around the room.

It gives the person you’re talking to a moment to compose themselves. It gives you new ideas to talk about from around the room. Most importantly, it cuts the awkward tension of small talk. [Read: How to make small talk without ever feeling awkward again]

5. Use what’s around you to make a conversation

When you look around in the middle of a conversation, you’ll always find something new to talk about. Mutual friends, exotic-looking food, someone’s funny antics, the weather, a drink… literally anything you can think of will work.

Remember, the person you’re talking to might be feeling awkward, as well. They’ll appreciate any new conversation topic you bring to the table!

6. Silence is okay

There’s nothing wrong with a bit of silence in a conversation. What matters is how comfortable you are handling that silence.

If you look and feel comfortable in a moment of quiet, the other person will start to relax, too. Remember that you can guide the pace of the conversation or let the other person know there’s no need to keep talking. This all starts with appearing as cool and relaxed as you possibly can. [Read: How to talk to anyone you come across and master the art of a real conversationalist]

How to keep a conversation going for as long as you’d like

Once you’re past the hellos and the pleasantries, use these tips to stretch the happy conversation until it naturally progresses into something far more interesting and fun.

1. Open-ended questions

If you’re interested in prolonging the conversation, always ask open-ended questions. Answer any question you’re asked with another question so your new friend can respond to you with their own views.

2. Use their answers to create more questions

If the person you’re talking to says they like something, use their answers and create questions to find out more about their interests.

With each new question you ask, you’ll be able to visualize several other questions that can help you know more about this person and make them feel more involved at the same time. [Read: Secret words to easily prolong any conversation]

3. Compliments

“I’m glad I met you here! This place would be such a bore otherwise.”

Saying something nice will help the person better warm up to you. A compliment or two is a pleasant break from the typical conversation of questions and answers.

On a cautionary note, compliment the person you’re talking to only when you have been talking for at least a few minutes. Using them too soon can seem creepy and desperate.

But if they mention something that they’re proud of, like a promotion, make sure you use the circumstance to compliment them about it. [Read: How to compliment a girl – 15 must-know tips and 35 of the best lines]

4. Be comfortable during the conversation 

If you feel uncomfortable or awkward, the person you’re talking to will immediately sense the discomfort you’re feeling, and that will only make both of you feel more awkward.

Relax! If you use these tips on how to keep a conversation going, you’ll know everything you need to know. There’s no need to feel stressed by the conversation. You know what you need to say, don’t you?

5. Smile and nod along when they’re saying something interesting 

Be warm when you talk to someone, especially if you’re trying to impress them. Smiling can do two things. It can let them know you like their company, and it’ll help them feel more relaxed around you.

Nodding makes people believe that you can relate to what they’re saying. They’ll continue talking enthusiastically as long as you’re nodding along. [Read: How to be more interesting]

6. But don’t just smile!

Smiling and looking around without saying anything makes everything seem much more awkward. If you smile, make sure you say something to continue the conversation as soon as you look toward them again.

7. Don’t fidget

If you want to overcome the awkwardness, stop fidgeting. If you start fidgeting or looking around because you don’t know what to say, you’ll end up fidgeting a lot more in your efforts to cover your awkwardness.

Stand or sit down calmly and just look around to find a new topic to talk about. 

8. Be interested

Seem genuinely interested when you’re talking to someone you’ve just met. Try your best to look focused and avoid appearing distracted. Distraction is an annoying insult to someone who’s taking time to answer you or have a conversation with you. [Read: 23 interesting questions to ask a girl over text and get to know her]

9. Stop judging yourself

It’s completely acceptable to say something silly or stupid now and then. Stop holding yourself back in fear of saying something that you think will be judged. People are forgiving and likeable if you seem like a relaxed person, so just laugh at your slip-ups, and no one will care! [Read: How to be comfortable with yourself – A guide to stop caring so much about what others think]

10. Involve the quiet person

If there are more than two people you’re talking to at the same time, always make sure you involve the quiet or bored person. This person is a weak link and the ticking time bomb who can make everything way more awkward.

If you notice someone fidgeting or appearing bored, involve them in the conversation by asking for their opinion. They can join in, and their bad energy won’t rub off on others who are enjoying the conversation with you.

11. Ramble on

It’s completely okay to ramble for the first minute. Don’t use a filter to avoid saying something just to appear cooler or more uptight. For the first couple of minutes, just say the first thing that comes to your mind *unless it’s totally inappropriate*.

It’ll help both of you feel at ease around each other. [Read: 50 funny conversation starters to keep you laughing and talking for hours]

12. Your goal is to find a mutual interest and click

Here’s the most important part of knowing how to keep a conversation going with someone. You need to find that mutual interest that can connect you together.

In every new conversation you have with someone new, the first few minutes are all a stab in the dark. You don’t know them. They don’t know you. It just makes everything more awkward.

But if you want to build on the conversation and turn info into friendship, you NEED to find that common ground. 

Ask lots of questions, share a lot of your thoughts, and you two will find something both of you have in common that’ll bring you closer. [Read: How to be likeable and be adored for who you are]

13. Don’t be overeager

Never be an eager beaver waiting to please. Don’t talk about meeting up again sometime, or try making plans to catch up for a coffee date within the first couple of minutes.

You’ll just end up coming off like a clingy leech. [Read: How to make someone like you – 25 ways to draw someone closer to you]

14. Introduce yourself well

If you’re being introduced to someone or a group of people, introduce yourself warmly and look around and make eye contact with each individual person. You could use a witty ice-breaker if they’re all expectantly looking at you to say something, or you could just wait for someone else to say something.

There’s no hurry to take centerstage. [Read: 60 funny ice-breakers to spark a funny conversation with anyone]

15. Approaching someone yourself?

Instead of walking up to someone and just telling them who you are, lead with a topic. You have to start a conversation before you can hold it.

Otherwise, that person might look at you and question why you’re trying to talk to them in the first place. Just starting with your name isn’t valuable to them. You have to start with something that’ll engage them right off the bat. [Read: 25 great conversation starters for when you’re drawing a blank]

16. Connect the dots

There are a few things that connect all of us and help us to get talking. Use them, and everything just gets easier from there. Remember these five basic conversation starters that work every single time!

1. The weather

2. The place you’re in at that moment

3. What do you do for work?

4. A mutual interest

5. Something interesting that’s happening around you

There are many other ways you can initiate and hold a conversation with someone, but if you can use any of these five starters, you’ll be able to build a connection with the other person instantly. [Read: Flirty conversation starters – the 30 best ways to start a conversation and get something going]

17. Pick what catches their eye and talk about it

Once you connect with someone by asking any of the topics above, keep an eye on what makes them respond to you with enthusiasm, and talk about that connection.

People naturally want to talk to others they have a connection with. You have to draw a connection between the two of you. It can be about anything, really. Make sure they know you have something in common, and it’ll be easier to hold the conversation because they’ll be putting in the effort, too.

18. Make sure your body language is inviting

You can’t sit there looking bored with your shoulders slumped. Stand or sit up straight like you’re actually interested in hearing what they have to say. Be sure your body is facing them and that you’re focused on them.

The more easy-going you appear and the more interested in the discussion you look, the more they’ll pick up on these positive vibes and want to keep talking to you. [Read: Subtle body language moves to appear more confident]

19. Listen to others

You don’t have to start talking as soon as you’re introduced to someone. There are a few talkers who do this, and there’s nothing wrong with it. Maybe they want to dominate the conversation, or maybe it’s just in their personality to want to be the center of the room.

But instead of appearing interesting, these people often come off as pompous or seem to be trying too hard to let others know that they’re more important. You don’t have to do that.

Pay attention, and listen to others and what they’re saying. When you’re great at something, you don’t need to rush in to prove how good you are. [Read: What makes people like someone? 35 things that people always look for in people]

20. Don’t start talking with a contradiction

If you want to know how to hold a conversation with someone, remember that it’s a conversation, not a debate. You may have come across many people who love to contradict others. They assume that contradictions are the easiest way to have a passionate conversation. 

Debates may be great among friends who know each other well. If you want to hold a conversation with someone new, however, it’s not the way to go.

A debate always makes one person feel stronger and more powerful and makes the other person feel weaker and annoyed. Unless you’re trying to put someone down, avoid picking a fight with them just to make yourself feel better. [Read: How to be nice – 20 easy tips to make everyone love being around you]

21. Be open to accepting the other person’s point of view

We live in a world where everyone has differing and opposing views. Just because you’re right doesn’t mean the other person is wrong. It’s just your point of view.

If someone has another perspective or way of looking at something, that doesn’t make them wrong. If you want to know how to hold a conversation with someone, be open to accepting that different people can have opposing views.

22. Don’t argue

People argue when they lose their cool. There’s literally no reason for anyone to feel hot under their collar. Stop taking things so personally in a conversation. It’s their view, and their view has no bearing on your life or your opinions. [Read: How to be classy – 20 classy people traits that command awe and respect]

23. Lift yourself up without pushing someone else down

You can explain yourself without having to put someone down. You don’t have to be nasty or mean to get your point across. You don’t have to point out that you’re right and they’re wrong. If you’re right, people around you will know that all by themselves.

Allow people to see how graceful you are, whether you’re talking or listening.

24. Have some ideas and ice-breakers in mind to steer the conversation

You’ll run out of conversation topics if you don’t keep any in mind. That just happens sometimes. Clicking naturally with the person will help alleviate some of this, but that doesn’t always happen right away.

Keep a list of different ideas in mind so that you can keep the conversation going once it starts to fizzle out. If it gets to that point, you have to work hard to maintain an exciting discussion so that it won’t completely end. [Read: 20 intriguing conversation ideas to keep the discussion going]

25. Let the conversation carry on naturally

Sometimes, it just will. You don’t have to force it, and you can just sit back and enjoy the conversation. Knowing how to hold a conversation has a lot to do with knowing when to let it flow and when to put more effort in.

If things are just carrying on by themselves, let them. Don’t interrupt one topic just because you think you have to introduce the other ideas you had in mind.

26. Use humor fairly often

People enjoy the company of funny individuals. That means that in order to keep the conversation going, you should throw in some humor. Make a few jokes, and see where things go. The more they enjoy having you around, the easier it’ll be to hold the conversation. [Read: How to be funny and make people love your company]

27. Don’t put too much pressure on yourself

If you’re worried about keeping the conversation going, you won’t be fully immersed in it. You have to just relax and let things happen as they should.

The more you worry about it, the more noticeable it is. You’ll be stiff and nervous. Those aren’t very approachable qualities, and it’ll put people off. Have some confidence and just talk to people. Form connections, and if the conversation is over, just let it be over.

28. Know when to transition out of a topic

If you’ve been talking about the same subject for the last half an hour, it’s time to move on to something else! Learn to read the signs of when someone is bored of talking about something and find something else.

Most subjects naturally transition from one thing to another. You just need to understand the right time to make the leap. [Read: How to be more social – 22 ways to genuinely connect with others]

29. Gossip, but keep it non-toxic

It’s a fact that people bond over gossip. However, you don’t have to go down the toxic route and talk about people behind their backs. There are many non-toxic routes you can try.

You can gossip about the weather, about the latest installment of a popular soap opera, or anything that doesn’t involve personally attacking another person.

30. Know when to stop

Sometimes, no matter how hard you try, a conversation just doesn’t flow. That’s okay. Understand when to walk away with a polite, “Nice talking to you.”

Trying to keep a chat going that’s obviously dead in the water won’t make you look or feel good. [Read: Easy ways to avoid a first impression catastrophe]

The five best conversation-makers for enjoyable conversations

Conversations have to be fun and interesting, and they only get interesting when the two people conversing have things in common. After you’re done with the introductions, you need to try and build the connection so that your new friend feels like they have something in common with you.

If you want to keep a conversation going, here are the best things you can talk about that will definitely help find common ground between both of you.

1. The location

The place you’re in is a perfect way to get to know each other without getting personal too soon. Talk about where you are at that moment and about anything you see around you.

2. Work

Work is a good impersonal conversation topic to talk about in the first few minutes. If you know something about their line of work, appear interested in it and ask a few curious questions, or talk about what you do professionally. [Read: Love or career – how to choose and make sure you’re not left feeling bitter]

3. Beyond work

Everyone indulges in a few activities beyond work, be it hobbies or watching movies on weekends. As you talk about work, try to involve other activities in your questions by saying something like, “Your work seems rather hectic! You must be doing something to blow off steam during the weekends…”

A good conversationalist always tries to flow from one conversation topic to another without going off on a tangent and just bouncing from one topic to another.

Whatever you ask, find a way to incorporate the answer into another question. [Read: 20 ways to perfect your conversation when you’re on a date]

4. Talk about a common factor

There must be something in common between you, and that’s always a great way to break the ice or go into something more personal.

Talk about the friend that introduced you, the host of the gathering, or an activity that you both enjoy.

5. An incident you experienced a few minutes ago

Funny anecdotes or fresh stories are always great ice-breakers that help you share a laugh. Did you experience anything funny, like spilling a drink or tasting something that was revolting a few minutes ago?

If you want to make someone feel comfortable and like you, you need to make them laugh at the most opportune moment. [Read: Everything you need to know to be funny and make people love your company]

6. You can use a few conversation starters

If you have a hard time using any of the topics above to keep a conversation going, just use an appropriate conversation starter.

They always work. Unless you use something that’s obscure, the person you’re talking to will be happy to indulge you unless they’re just waiting to get away from you. Use these 25 perfect conversation starters that work anywhere to get the conversation going.

Giving up and second chances

Even the best conversationalists have to deal with grumpy company now and then. If someone’s clearly not interested in talking, don’t blame yourself for it *unless you’re a bore who’s not following these conversation tips*.

If someone excuses themselves after a few minutes, don’t force them to continue the conversation. If you really like them and want to get to know them better, you could always “accidentally” bump into them when you find them alone and bored after a while or if they walk past you later in the evening.

All you have to do is look toward them, slow down just a bit, and smile. You can also just wave or raise the hand holding a drink ever so slightly. If they’re interested in talking to you, they’ll walk up to you and may even be happy to talk to you this time around. [Read: 15 obvious flirting signs between a guy and a girl]

Dealing with bad conversationalists

Are you the only one asking questions or making conversation? Do you really like this person so much that you’re willing to throw yourself off a bridge to continue the conversation?

Here are three bad conversationalists and different ways to deal with them. [Read: How to deal with rude people]

1. They’re not interested

If someone isn’t interested in talking to you or is only answering with monosyllabic answers like yes or no, let them go. You’ll only annoy them and make them dislike you if you try to force them into a conversation.

2. Rude or cold behavior

Some people become rude or behave in a cold way to cover their own awkwardness. If you’re talking to someone who isn’t getting away from you, nor are they trying to converse with you, they’re probably the ones who aren’t confident about their own conversation skills. They find it easier to hide their awkwardness behind a wall of ungraciousness.

Be warm and friendly, and try to get them to feel more relaxed before you give up on them. [Read: How to get someone to open up to you so you can really connect]

3. The scared conversationalist

Almost all people are intimidated and awed by smooth-talkers. A few guys and girls take time to open up, especially if you’re an extremely smooth and confident conversationalist. If the person you’re talking to doesn’t open up quickly, take it more slowly.

Instead of being too smooth, pause for a few seconds every now and then before asking a question. By doing that, you let them believe that you’re no smooth talker either. It’ll take the pressure off them and give them more confidence to ask you questions in return. [Read: How to make a girl laugh, smile, and like you instantly]

Ending a conversation the right way

No matter how the conversation goes, end it warmly. Even if you couldn’t impress someone or get someone to fall for you, at least you have a new acquaintance or friend. Maybe if you ever do bump into this person somewhere else, you can still say hello and start all over again.

But if it all works out, and the person you’re talking to has fun talking to you, make sure you find a way to keep in touch or make plans to meet again.

[Read: How to impress someone you like – 20 ways to leave them thinking of you fondly]

The next time you’re wondering how to keep a conversation going, just use these tips. With these, you’ll never ever have any difficulty impressing anyone you meet, and you’ll have a great time, too!

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Vinod Srinivas Serai
Vin Serai
Vin Serai is the founder of LovePanky.com, and has delved deep into the working of love and relationships for almost two decades. Having dipped his feet in almo...