Art of conversing

Lately, I have been getting comments that people have been enjoying speaking to me. On the other hand, how have I?

A warning that this is far from teaching you the art of conversing but my cry for help on how to converse.

Conversations. The play that reenacts often in my head and the flow that I get into daily.

These days when I have been dating or getting to know people, I often feel neglected that I had been playing my part in getting to know them by showing interest in asking questions. Yet, it’s not reciprocated.

I perceived it as others having bad conversation skills (unlike me). Why are they not continuing the convo by asking me back? Isn’t it courtesy to do the same for others? It felt like I was giving them the stage to share their thoughts while I take the audience seat, play after play. If the play was exciting, I’ll come back. If it doesn’t, I do my part as the attentive audience to clap and encourage for more. All the while eyeing to have the centre stage.

(It’s probably not so dramatic, but it paints the picture)


I often plan questions ahead of time in fear that we run out of topics to talk about. That silent space of not having a conversation when it feels like we should, became my gauge of interest and sense of belonging.

I felt this shift of importance come about when I started focusing more on the quality of relationships and especially on new, foreign ones. As I talk to more people, I began to be conscious about how much we can talk as part of my benchmark. While I focus on maintaining the flow, I keep my questions coming and I notice their lack thereof. Because I make an intentional effort to keep in going, it disappoints me when I don’t find that they do it back.


There were 3 occasions where I reflected more about the art of having a conversation:

  1. In getting to know my dates
  2. Deep talk with my friends
  3. Small talk with colleagues
(1) In getting to know my dates

When it comes to meeting a stranger, it really excites me because there’s so much unknown about this person. Everything is a new fact (and learning)! As time passes, I grow invested in this person and I pick up many things about them. With all these new facts, we delve deeper into who they are.

I’m not sure if it’s because I haven’t met someone right or if it’s in the way I communicate, I find that I learn much about the other person, yet I am stuck in my own thoughts. As questions are my gauge of interest, I find that they don’t ask me because they are not interested to hear my pov. And if I don’t get to contribute to our topics, how invested can I get in the convo? 😦

One friend analysed it as that the other party is also excited to share more and impress me about what they have done! I probably have made them so interested in themselves that they forgot I exist in the conversations too.

The finding I got out of this was that while I was looking for the catalyst to encourage my conversations, perhaps I needed to be my own audience. I need to butt in bravely regardless of whether they will find me boring because I am my own interesting person too! My benchmark can shift: Questions don’t necessarily equate interest.

(2) Deep talk with my friends

I was discussing religion with my friend over a meal one day. I wanted to know her relationship with her faith. After the talk, she told me that she wasn’t very keen on sharing initially, but my questions kept the conversation flowing and her mind active. She became engaged and took things out of the conversations.

Her comment was really raw and it made me think!

She said that I showed genuine interest and wanted to know her opinions. The questions that flowed out of me this time were fluent, they were out of interest rather than intent.

I admitted that there are moments in the conversations that I drift away because I lost focus or wasn’t interested, but she shared that it was packaged well within my cues. That was also normal and it’s up to how the conversation flow to direct it back to something mutual!

There was also no need for me to intentionally keep the talking going. We can have moments of silence to process the things around us. Take things easy.

Another friend broke it down for me that it’s also heavily dependent on the person that you are speaking to. We have all matured and found a way that we are most comfortable with speaking. If asking questions was my way, others could have another way of communicating. If questions are what I am looking for, then I may have to find someone who cherishes this way of conversing too.

I think what I took away was that conversation is a tennis match, the effort to keep the ball bouncing comes from both parties. If it was tiring, it could be that it wasn’t communicated clearly on what interests you. It is also time that you are investing, talk about it! Else, time to change for a worthy opponent.

(3) Small talk with colleagues

“How was your weekend?” I actually love small talks that help break the ice and warm the mind up. It loosens tension and is a safe zone – factual and positive answers. The only small challenge I have is knowing when to break and transit back to work talk.

Even after talking for 20+ years, I still have trouble gauging when to initiate / continue (in fear of awkward silences, interruptions and clashes). These days I put in my effort in slowing down myself and allowing room for a natural flow.

I was walking with my colleague the other day to find a can opener. While I was asking for her weekend, I found myself wanting to ask more questions after every “full stop” aka pause. Each time before my question spills out, my colleague continued with more detail without my prompts!

I thought about how if I had butt in, I may have disrupted her planned flow and changed her original thoughts. I just had to pause a bit more and others have it in their sleeves. It made me reflect on my need to quickly offer my 2 cents. Perhaps it was the fear of having awkward silence or my competitive need to feel smart and chip in, I realised I don’t need to try so hard.

Things have their natural flow, and I just have to pause and let nature takes its course. I have to learn to pause before I open my mouth. Conversations should be smooth and easygoing, not a job to ace!


Overall, from these 3 scenarios, I’ve gathered that conversations can be an intentional stroll you embark on an interesting two-way street that is dependent on who and where you are with and at. Some walks may be smooth sailing, some sceneries may excite you and some may have you stop at one end.

Honestly speaking, I probably overanalysed this, but writing this down and talking to people has made me realise that it’s not that hard. I had cared too much about this and spiralled into an existential crisis. Learn to let go and things will flow naturally!

Curiosity in people has always been a trait of myself that I adore, all I need now is to converse with people who are the same! Keep asking and learning, I believe I do learn about myself from listening around too.

Maybe one day I’ll also write / internalise about the selfishness behind one’s curiosity. How it quenches one’s thirst for knowledge, but could possibly be at the expense of another’s privacy.

Thanks to those who enlightened me in this finding, and to those who I love sharing a coffee with. ❤

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s