A guide to a good random conversation

Vishwarath
6 min readSep 29, 2016

When I recollect stories from my past, random encounters and conversations stand out. That’s because they unfold in the most unexpected way and remain etched forever.

From an unforgettable conversation with an independent musician to a strange girl on a bus who was on her way to meet her boyfriend for the 1st time to a coffee planter in Coorg who let me hitch a ride to the nearest town to a guy on the mountain top with whom I shared my tent.

I consider myself an introvert, I find it extremely difficult to start a conversation. Even if I manage to start one, I struggle to keep it going. Startup, travels, my job and living away from home drove me out of my comfort zone and pushed me to deal with this problem.

This piece is a reflection of what really worked for me and few things everyone can take away if they are looking to enhance quality of conversations.

#Tip 1, Smile and wave, Boys!

Don’t wave. Just smile! Not a creepy one but a gentle one should do. I think the Indian society in general, is an introvert society. We are not really good at starting a conversation. We don’t even appear welcoming to another person looking to start a conversation.

A smile creates a gentle and warm aura around a person. The body language significantly changes when you are smiling and so does your tone of communication in general. I think it is the single most important habit to create.

#Tip 2, Do not hide behind the curtain

When I am in a room full of new people, I usually wait for a common friend to introduce us. I found that it really makes a difference when I proactively reach out to people.

If there are many people in the room or at the table, go around and introduce yourself. It brings down the barrier between two people, naturally opens up the conversation and other person is more likely to make an effort to keep the conversation going.

Initially, fear and insecurity stopped me from talking to people at random. Only when you reach out to people you realize how alike and special we really are. What’s the worst that can happen if you initiate a conversation? You will not be arrested (not sure about North Korea though)

Remember to keep your smile on and ensure that the other person is comfortable.

Please, do not do this!

#Tip 3, The Introduction — Repeat and remember the name

I have a terrible habit of not remembering names of people I used to meet. It gets kind of embarrassing sometimes when you can’t recollect someone’s name when they are staring at you. In such situations, I just want to bury myself or disappear into thin air rather than facing the music.

I made a few changes to the way I introduce myself to people. This is how I do it,

Me: Hey, I am Vish.

Stranger: Hi, I am Paul.

Me: Hey Paul, Nice to meet you.

Repeating a name is good. One, you are making genuine effort in knowing the other person. Two, it makes it easier to remember his/her name.

When I proceed with the conversation, I address him/her with their name. The quality of attention I get from the other person is completely genuine. Later if you do not remember their name. It is okay to confirm it once again before you start the conversation or towards the end.

#Tip 4, The Hook

Hook is a take off point of a conversation. It has to be smooth and solid. It is important not to falter midway. Sometimes, it can be a book or a tattoo or music. Sometime it can be as random as asking for an advice.

Universally, complimenting a person works really well and when you ask them more on the subject, they really love talking about it.

Hook is an extremely situational thing and I generally don’t prepare for this because it can either make or break the conversation. I like to be very careful about this because you need to be natural and genuine.

#Tip 5, The Curiosity

The golden rule for any conversation is to show interest and be curious about the other person. Everyone’s got stories, tales, anecdotes, hobbies, likes/dislikes etc. You need to ask the right questions and be genuinely interested.

Stories are a great way to keep your conversation going. Story telling is an art but you don’t have to be a master at it to keep going. Another trick is to keep it contextual. If we are in a restaurant, I talk about different experiences I had in a restaurant and then I ask the other person if they experienced anything interesting.

You sometimes need to open up to make the other person comfortable and at the same time you need to let them talk.

#Tip 6, Find an anchor point

I often run out of topics and then hit a dead end. Then comes the awkward silence. To avoid this, I look out for anchor points.

Here is the thing about mass media delusion. We all consume and survive on 90% similar stuff. Most of the people in my age group watch GOT, they all are huge fans of Harry potter or LOTR, either Star wars or Star trek and love Friends. Based on the background of the person, it is quite easy to get the anchor points.

If you have absolutely nothing and luckily if the opposite person is from Banglore, just talk about traffic. Nothing like bonding over Bangalore traffic. True story.

#Tip 7, Beware of conversational suicide (stuff to avoid)

I often start well but soon we fall short of words and run out of stuff to talk about. In moments like these I fall back to the most boring words — ‘What else?’ or our phones.

Please avoid the following sentences,

What’s up?
Suppp!
So, What else? etc.

This is what happens when someone asks me ‘whats up?’

Stranger: what’s up?

Me: em ( thinking where do I begin? Should I talk about my life in general? No, that’s a long story. Oh wait, I can tell her about the dinner last night.. Aah but that’s boring anyway..)

Me: all good .. Nothing much

Stranger: ah okay .. That’s cool :|

There is no coming back after that. I like to keep my conversations flowing. I do not like speed breakers. Unless you really know the other person avoid using these sentences and look for something more concrete on which you can build the conversation.

Speaking of flow, keep your phones away. There is nothing more annoying than being engrossed in to your phone when you are in conversation with someone. That is extremely rude.

Today, we express using emoticons, make friends at a click of a button and choose a partner by swiping left or right. Being a 90s kid, I feel that Internet and I matured at the same time. Earlier, I preferred Yahoo chat rooms instead of heading out to meet people. Over a period of time, we’ve somehow lost signal with our own species.

It can be refreshing to have conversations with a random people. It opens up a new world, it can give you new ideas, inspire you to go on an adventure or hear some mind bending stories or like most of the time, helps you pass time and nothing more. Get out of the building!

Btw, when you talk to actual people you are not disturbed by scrolling advertisements. They are advert free.

Thank you for reading my post. I would love to interact with people who have feedback to share or just for fun. Reach out to me on twitter .

PS: Shout out to Nivedita, Nivedha and Abhilash for helping me complete this piece.

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