How To Start And Keep Interesting Conversations Alive

Written by Harini Natarajan

How do you keep an engaging and stimulating dialogue going with someone who doesn’t seem very interested in what have to say? There are so many things you can do wrong and offend the person, but there are also tried-and-tested ways to hold their interest without coming across as rude or annoying.

The basis of keeping a conversation seamless is to show how interested you are in what the other person has to say. You want them to be your audience and think how awesome you are because of how much detail you can go into about a topic they know entirely nothing about. If you show how much effort you are putting into making this conversation flow, people will stop dreading it so much. Keep scrolling to get a deeper insight into the art of conversing.

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.
  5. 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.
  6. 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.
  7. Try not to bring up controversial topics, such as politics, religion, and other sensitive issues, until you have known someone for a while.
  8. 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.
  9. 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.
  10. Make sure to share your honest opinions and feelings about specific topics. This will showcase your sincerity while engaging in conversations.

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

Amp Up Your Texting Game


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?’
  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?

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

Get Going With Someone You Just Met


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. 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.

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.

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.

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.

However, when 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

Keeping Things Interesting On A Date


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

Conversation-Saver Questions


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 physical traits make them confident (or not).

4. If you could have a superpower, what would it be?
A fun dialogue to start something exciting, 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.

Summing It Up

There are many ways to keep a conversation going. The key, however, is how you start a conversation and involve the other person to participate equally. Asking questions about their interests or sharing similar stories can be great ways to do this. So, get out there and start engaging more people today — we know you will love how easy it feels once you have mastered this skill.

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As Chief Editor, Harini sets the tone and editorial direction for StyleCraze to deliver engaging, interesting, and authentic content revolving around women's health, wellness, and beauty. She has over 14 years of experience in content writing and editing for online media. She specializes in the areas of Beauty, Lifestyle, and Health & Wellness and is proficient in Medical Sciences (Biology, Human Anatomy and Physiology, and Biochemistry). Her background in Biomedical Engineering helps her decode and interpret the finer nuances of scientific research for her team. Harini is a certified bibliophile and a closet poet. She also loves dancing and traveling to offbeat destinations.