How To Keep A Conversation Going & Keep Things Interesting

For all who struggle to keep up with the small talk, here's your guide on how to thrive.

Reviewed by Amanda Bennallack, Relationship Coach
Written by Shivani Chandel, MA (English Literature), Certified Relationship Coach
Edited by Subhrojyoti Mukherjee, MA (English)
Fact-checked by Sneha Tete, Integrated MA, Certified Relationship Coach  • 

Conversing is an art, and not everyone has that spontaneity and confidence while talking with others, especially when talking to new people. So, how to keep a conversation going without that awkward silence? Although you want to know the person around or the topic they are discussing, sometimes you may feel like running out of words to ask or say something.

Here the biggest problem is not knowing how to keep your conversation going. It not only misses the chance to know that person who is conversing with you but also your chance to prove yourself. However, with some practice, you can keep your conversation flowing without bumps. This article explores some key points to keep your conversations alive. Scroll down to know more.

Importance Of Conversations

Conversations are the heartbeat of connection. Your active participation in meaningful conversations fosters companionship, breaks down barriers, and creates a vibrant atmosphere. By sharing thoughts and experiences, you can forge strong bonds that establish a sense of belonging. It also helps you gain insights into diverse perspectives and grow as an understanding and empathetic person. An extra perk of being able to engage in fulfilling conversations is that it enhances your social skills, making you approachable and likable. It enables you to navigate different social circles, resolve conflicts amicably, and contribute positively to the collective energy of the group. Ultimately, your adeptness in conversation enriches social dynamics, turning casual interactions into lasting relationships.

Conversations are what sets us apart as human beings and it is extremely important to know how to keep conversations alive and interesting. If you need some help, the tips below are a good place to start.

Key Points To Keep Conversation Alive

Adopt the following measures when you find it difficult to initiate conversation or keep the ball rolling with someone:

  1. Ask how someone’s day is going (or has been) and how they feel about it. If their day was terrible, ask how you could help cheer them up. If their day was good, find out how to make the next one even better!
  2. Make sure they have a chance to talk too by asking them questions in response to what they tell you. This may involve summarizing their points and showing genuine interest in how they feel when it comes to a particular topic.
  3. Reflect on how they feel when talking about a particular topic or experience by paying attention to their body language. Steer clear of uncomfortable topics.
  4. Be aware of how your facial expressions may be seen as you engage in conversation. Ensure they are positive or neutral rather than negative or judgmental when you are conversing.

A blogger shared his experience about having a quality conversation in his blog. He wrote, “When someone speaks to me, I make an effort to have good eye contact, to actively listen in order to understand what the other person is saying. My hope is that I would be given the same attention in return. Isn’t that what a conversation is? An “exchange” of ideas? A two-way street (i)?”

  1. Try not to be too blunt or sarcastic when trying to respond to what someone else has told you, as it may portray you as uninterested or rude.
  2. Share something funny that happened the other day or how your day was. Sharing good and positive stories shows that you are a happy person and easy to get along with.
  3. Try not to bring up controversial topics, such as politics, religion, and other sensitive issues, until you have known someone for a while.
  4. Keep questions open-ended, allowing them to answer in more than a word. It will encourage the other person to talk more about how they feel.
  5. You may need to avoid asking questions you don’t care about if someone is not that talkative. Instead, try to ask questions that may interest them and, in turn, encourage them to open up and speak their mind.
  6. Make sure to share your honest opinions and feelings about specific topics. This will showcase your sincerity while engaging in conversations.
  7. Ask clarifying questions if you feel you’re not sure of the meaning or explanation they have given. This will prevent assumptions and demonstrate your interest and care. It will also give them an opportunity to expand their point of view.

The above pointers are relevant for all kinds of conversations we engage in. Let’s move on to explore how you can dazzle someone over text messages.

Amp Up Your Texting Game

Keep a conversation going by texting
Image: Shutterstock

Visual cues help a lot in face-to-face conversations, but they are missing when you chat on text. So, keeping this limitation in mind, here’s how you can make sure the other person has an enjoyable time:

  1. It’s all about taking an interest in them by asking good questions, listening attentively, and being willing to share some of your interests with them.
  2. One should have the conversation without being too nosy. Don’t ask questions that are too personal. Give the person an opportunity to share how they feel about something.
  3. The trick is to keep the conversation light and fun and avoid any topics that might make it uncomfortable or awkward. People like talking about themselves, so give them the opportunity! Also, pay attention to what they say and how they say it.
  4. Besides knowing how to ask questions, you should also be careful about how to answer them. If you only send one-word responses, like ‘ok’ or ‘cool’, how can someone reply and continue the conversation?
  5. The best way to sustain conversation is to ask open-ended questions like ‘What are your plans for this weekend?’ or ‘How was work today?’ “How do you feel about doing….this weekend?” “What suggestions do you have that you would like to do this weekend?”
  6. While someone is sharing an anecdote or story, don’t interrupt repeatedly. Also, don’t go completely silent. Ask questions at natural breaks in their story to convey your interest. If they haven’t finished their story and you ask another question, how will they know how to continue?
  7. Ask clarifying questions if you feel you’re not sure of the meaning or explanation they have given. This will prevent assumptions and demonstrate your interest and care.
protip_icon Quick Tip
You can avoid an awkward silence during texting by asking the other person about something they shared about themselves earlier with you.

These days, texting has become a preferred mode of communication for many. However, there are times when you come in contact with someone at a social gathering and need to initiate conversation. Don’t worry, we have got you covered.


Get Going With Someone You Just Met

Keep a conversation going with someone you just met
Image: Shutterstock

It happens all the time — you meet someone new, exchange pleasantries such as ‘hello’ or ‘good morning’, and then that’s it. Even if you are ready to continue the discussion, you run out of things to talk about and later regret it. It’s important to have a curious mindset, this will help you stay focused on what they share. People like talking about themselves and when we ask good open-ended questions that lets them talk about what interests them and why, they will feel heard and organically build strong rapport. Here are five questions you can ask them to get the conversation going:

1. What do you do for a living?
This question gives the other person an opportunity to talk about how they spend most of their time. It is also an excellent way to find a common ground and determine whether or not there is a potential for friendship. To get an insight to what they enjoy about their work you can ask:

What do you like about your work? This digs deeper into why they do the work they do. We spend 8-10 hours a day at our work and it must provide some form of satisfaction. When they answer this question it will reveal what they value about their work besides the income!.

2. Where are you from?
Every person is from somewhere, and it is always interesting to find out how far the other person has traveled. This simple question is a good ice-breaker because there are so many ways to answer it — their state, country, or part of the world.

3. What do you like to do for leisure?
The other person will indeed say something they enjoy. It might not be the same as you, but it is an excellent way to establish a rapport and determine how much you have in common. Expanding on their personal interest you can then ask:

What attracted you to doing…? This will reveal what brings variety and passion into their lives? We value our free time, so what they choose to do with it will reveal what is important to them and why.

4. What would you like to do more of?
This question is meant to open a discussion that allows both the participants to share something that they hold dear and figure out a way to fulfill that desire. For example, if one person wants to go on more hiking trips, how can they make this possible?

5. What’s your favorite place?
A good question to ask when you want to get to know someone better is the kind of places they enjoy being at. The answers could range from a mall, bedroom, and lakeside to a beach or a hill station and can form a basis for further interesting talks.

protip_icon Pro Tip
You can plan your next date or a weekend trip to a place they love. This will deepen your relationship and give you some brownie points showing you paid attention to their preferences.

All of these questions are relatively simple, so it’s easy to remember them when you want to keep a conversation going. However, remember that how well the conversation flows will depend on how much you have in common, so try not to focus too much on how long the discussion lasts.The point is to pay attention to what they are sharing and listen to understand them, not to listen to respond!

However, when you are out on a date with someone you like, you try and make the conversations go on and on. Here’s how you can woo your date with your gift of gab.

Keeping Things Interesting On A Date

Keep a conversation going on a date
Image: Shutterstock

Dating doesn’t have to be daunting if you know how to keep the conversation going and stay confident. Keep the following points in mind to impress your date with titillating conversations:

  1. The best approach is to maintain eye contact and avoid interrupting the other person. Give them ample opportunities to share their thoughts. If they seem hesitant, you can lead with a question. Perhaps, you can ask how they like their food. This way, they get a chance to talk.
  2. Keep in mind that when you initiate a conversation, it can be helpful to find out how much they want to chat. This way, you won’t end up talking more than they want you to. If they are going to speak, you can do the same.
  3. When talking about your experiences, make sure that you avoid bragging and focus on how you benefited from them. For example, if you are talking about winning a marathon, focus on how it helped you to be fit or taught you the importance of teamwork.
  4. Another critical component of how to keep a conversation going is how you respond. You can maintain the flow by providing pertinent and concise answers and asking questions that would tell people more about who you are as a person.

Whether you are completely terrified about your date or just want some ideas on how to start a conversation with someone you have met for the first time, these are some constructive questions that may help you discover what kind of bond you share. You may never know until you ask!

Conversation-Saver Questions

Keep a conversation going by asking questions
Image: Shutterstock

1. What are you most interested in at the moment?
This question can lead to a conversation about many things — work, personal life, relationships, hobbies, and so much more. It will broaden the discussion because it includes various responses that may overlap with your own personal or professional life. Also, asking this question allows the other person to talk about something they’re passionate about.

2. What’s the best thing that’s happened to you this year?
This question will give you a good insight into how someone’s year has been and how they feel about it. It can lead to a discussion on how your year has been as well. Then, add your twist with another question, like, ‘How would you rate this last year out of 10?’

3. What do you like most about yourself?
Asking this question can lead to an interesting discussion that may or may not include how someone’s appearance plays a part in how they feel about themselves. It also sparks conversation about how much confidence one has and how their work skills, communication, athleticism, or personal traits make them confident (or not).

4. If you could have a superpower, what would it be?
A fun dialogue to start something exciting, to know about how someone might use a superpower, and how they feel about being so powerful. It can also lead to how other people around the world might view superpowers and how different cultures have different perspectives on this topic.

5. What’s something that always makes you laugh?
This is an excellent question because it may lead to how humor plays a part in someone’s life. It could also be humorous how they answer it – for instance, something specific that makes them crack up. You can also ask how humor has impacted their life.

6. How would you describe yourself if you had to use just three adjectives?
A straightforward question that can lead to how someone perceives how others view them. It is also revealing how much thought they have put into their answers. You can also ask how their friends might describe them or how they are in different settings.

Not everyone possesses the skill to keep a conversation going, while it comes naturally to some. However, you can improve your conversational skills by choosing the right approach, like keeping your questions open-ended, bringing up topics that interest the other person, avoiding controversial topics, being honest, and not being blunt or sarcastic to their responses. More importantly, do not restrict your replies to ‘yes’ or ‘no’ as it can discourage the other person from talking. Also, try to keep the conversation light and fun, and do not get too personal in the early stages of getting to know someone. Follow the conversation-saver questions listed above to keep the other person equally involved in the conversation.

Key Takeaways

  • There are many points to consider when trying to continue a conversation, such as showing interest in the other person’s day or opinions.
  • Another interesting way to keep talking is to text them on shared online forums or social media apps.
  • You can keep the conversation going by taking an interest in where they are from or what they do.
  • If you are on a date, one of the best ways to keep the flow going is to maintain eye contact and respond to what the other person says.

Learn how to keep the dialogue alive and effortlessly navigate through and hold engaging conversations. Take a look at this video for expert tips to master the art of verbal exchange.

Personal Experience: Source

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