The Paradox of Good Conversations: Showing Interest vs. Being Interesting

Hi there! Today I’d like to talk about what it means to have good conversations: with strangers, with friends or family or even with dates. As I described in one of my first blogs, I see myself as a so-called “Ambivert”. I’m not extraverted, but not introverted either: it largely depends on the situation. Lately, I’ve been thinking about what this means for conversing with people, getting to know them and letting them to get to know me. In my previous blog, I mentioned that it’s sometimes hard for me to be really out there, to try and have good talks with people. When I’m around people that don’t really know me well yet, I’m constantly concerned about how they perceive my silence (when I don’t talk) and social skills (when I do talk). I know I shouldn’t focus on it so much, as people don’t focus on ME that much! Everyone is paying more attention to themselves than that they are to you, so I shouldn’t be so worried. It’s not that I’m that insecure, or want everyone to like me, but in general, I feel like I’m now over-compensating  on showing interest, which makes me less interesting for other people. You might think now whaaaat that’s silly, of course that’s not true! And probably it isn’t, but it’s something I’ve just thought about quite a bit over the last few months. This is the paradox I’m referring to: showing interest and being interesting don’t go so well together quite often! I’ll illustrate some situations to explain it  all better :)

Asking questions

Small talk. The key for meeting new people, and something I’m awfully bad at! It’s not that I don’t dare to talk to new people – I genuinely love to meet new people – I just find it very hard to find topics to address when you don’t know your common interests yet. However, I think I’m getting better at it, so that’s not the major thing I’d like to discuss. I think after the first steps are made and as soon as the conversation is running, more and more questions are flowing in my mind. However, this enthusiasm that then comes, might also come across as an interrogation: it might scare people away, while I’m actually trying to be social (also out of sincere interest) and hope that people think of me as a fun social person. Also, it might seem that you don’t have much to contribute to the conversation yourself! So yep, that for me is a paradox: there is a thin line between showing interest and being social and asking too many questions and look clingy/boring?


I’m definitely not a storyteller. It’s not that I haven’t experienced any cool things in my life (not at all!;)) but in my mind, I think that telling my stories is not so interesting for people to hear as it’s too one-sided for a conversations. However, I’ve noticed that I do really enjoy people telling stories, so probably they would also really enjoy hearing mine! But then there is the next paradox: I don’t enjoy talking too much about me, I’d love to hear more about the other person than the other way around –> Leading to the above-mentioned interrogation problem again ;) While on the other hand, I also really do would like for people to ask me things that allow me to tell stories.

I’m just mainly surprised about people telling stories that are not really relevant to the context of the conversation, like: why would you tell about something randomly that has no correlation whatsoever to the talk you are having. Are your thoughts just drifting away from the conversation and are you then just thinking out loud? Why would anyone want to hear that? If it’s in general a nice story (even though it came out of nowhere) I of course don’t mind, but it also feels to me like people who do that are too much focussed on themselves and are actually paying too little attention to the other person. I personally think, when you feel like you’re done talking about a certain topic: come up with a question about another topic for the other person to answer! Instead of telling a random story about yourself.. Or is that me being silly again? As soon as I noticed a person does that, I get quite frustrated and feel like it’s a useless one-sided conversation.


A friend of mine once told me: When having conversation, you have to respond to what the other person is saying 2-3 times before you start talking about yourself or your experiences/thoughts on that topic. I really like that idea! When you focus on it, you can really notice a lot of people don’t do this, when someone is telling something, the other person tells a story of their own right away. Is this having good conversations (even though the story might be related)? Seems to me like you’re not really interested in the other person’s experience/idea/perspective, you’re not really listening and frankly, quite egocentric.

Pff, you might already notice I can go on about this forever ;) You might also think I’m totally overthinking it, while I personally think I’m not. I think more people should pay closer attention to what it means to have good conversations. Ernest Hemingway once said: “I like to listen. I have learned a great deal from listening carefully. Most people never listen.” I couldn’t agree more, you can learn so much from each other! I event think people don’t even talk enough anymore, due to mobile phones etc (but that’s another story) Well, let me get to an end of this post. I’ll provide some tips from my perspective on what a good conversation entails: creating a good balance between showing interest & being interesting. I might need to teach myself some of these points too, I can learn a lot still ;)

My conversational tips!

  • People like mystery, not when you’re dating someone, but if you leave somethings vague, it might trigger them to ask further and further. Which makes you more interesting for a person
  • Don’t bombard people with questions, react to something a person is saying with statements, general responses, or a question and then give your own take on it!
  • Try to think aloud, you might think the things you’re thinking are not so interesting to share right away, but I personally think a lot of people do it. Sometimes your thoughts are out of the blue, but they do enable new conversations!
  • Appreciate silence, don’t get nervous when you don’t know a topic right away, sometimes it’s good to not talk for a moment and give yourself sometime to think :)
  • It’s OK to talk about yourself, your thoughts, your opinions. You don’t have to push the conversation away from you, don’t feel like you’re less interesting to listen to than the other person! Appreciate being in the spotlight sometime, but make sure you put the other in the spotlight just as much
  • Speak aloud, don’t let people overrun you, if you want to say something, say it firmly and strong, don’t mumble!
  • Read the news daily, it’s a great conversation starter! Try to talk about things happening in the world around you more, instead of talking about other people and daily events (I personally love the quote below)!
  • Become an interesting conversationalist by living an interesting life, go out and experience different things, read books, do what makes you happy, see the world and don’t hesitate to tell people about it!
  • Switch fun talk with serious talks, sounds like a no-brainer, but really: you don’t have to constantly have interesting talks, don’t forget to joke around too!
  • I don’t know why, but my last tip is: When you’re not feeling so talkative, drink coffee!  May sound weird, but it personally gives me a talking kick. I’m way more energetic in my conversations after coffee, which I really enjoy!!


That’s it for now, it might seem like I’m overanalyzing every conversation I’m having: Don’t worry I’m absolutely not!! When you’re talking to friends & family you’ve known for years, I don’t think about it at all. It’s mainly with people I have less contact with, when I start noticing these things. However, this definitely doesn’t count for every situation, when you’re in a nice conversation flow, there’s not even time to think about how the conversation is going! ;) I just really like to learn about these things, watch how people function and see how I can improve myself, where needed :) I think I’m getting there! Of course, I’m very curious about your opinions and tips on this topic, so please leave a response in the comments or talk to me personally! :)





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