How To Be Different At Starting A Conversation - Deepstash

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How To Be Different At Starting A Conversation

  • When at a party, don’t ask ‘What do you do?’, instead, ask ‘What do you really want to do but cannot?’ or ‘Has your day lived up to your expectations?’
  • When a store clerk asks you ‘can I help you?’, reply with ‘can I help you?’

The point is to be different and vulnerable so that you sound intriguing and yet do not come across as a psychopath!

The Stranger On The Subway: Asking Questions

  • Asking more questions, especially follow-up questions, is more than just for gathering information. 
  • They help create deep, emotional bonds and make the other person feel better as they are being listened to, understood, validated and cared for.
  • Most people don’t ask enough questions about the other person as they are egocentric and are ready to fill in their two cents to the ongoing talk.

Most people sound despicable because they just keep on talking about themselves.

The Art Of Listening

  • While talking to strangers, we need to signal our engagement by summarizing or paraphrasing what the other person has said, to show that we were listening attentively.
  • We need to amplify our visible engagement with eye contact and nodding, as the other person does not know us at all, and is relying on the cues we send out.

From Really Bad To Okayish

Most of us are laughably bad at striking up good conversations with strangers, and can hope to improve ourselves if we learn what all is lacking to break the ice.

The conversation is mostly initiated by small talk, the opener that gets everything started. Most people hate small talk, but one cannot talk to strangers without initiating the conversation with something familiar and reassuring.

Talking To Strangers

Talking To Strangers

According to psychologists, talking to strangers can be taxing on the brain, and even small talk can seem stressful, tiring and cognitively demanding.

On the flip side, talking to strangers is a kind of workout that boosts our mental performance.

Being Human

Asking something specific and humorous to a stranger is a risk, but if the timing is right, one can give a great first impression about being complex, empathetic, humourous and human.

Once the stranger recognizes you as a human, a bond is created and real conversation can start.

Going Unscripted

We use scripted conversations to be on the safe side, as we fear that saying any unscripted word can trigger something unwanted in the other person.

While scripted conversations are efficient, they deny us the actuality of the other person, the stranger who may be just a friend we haven’t met yet.

By talking off-script or replying in a unique, unheard of manner, we make it comfortable for the stranger to mirror us and say something similar.

Triggering Conversations In A Suspicious World

Talking to strangers is worth it, as it offers a certain profound joy, a real communion. If more people start talking to strangers, our broken society can be healed.

  • The hardest thing about talking to strangers is the initiation of the conversation.
  • One has to approach with confidence yet provide an assurance that they are safe and don’t have any ulterior motive or agenda.
  • Older people initiate conversations more than younger ones.

Helpful Techniques To Talk Better With Strangers

  1. Proximity: Suddenly meeting a stranger and asking something will almost certainly fail. One has to be in the proximity of the stranger for a while to be accepted.
  2. Don’t Make It An Interview: Being too interested in the other person can backfire. You need not lean forward, ask questions quickly or interrogate them.
  3. Statements: Use statements instead of questions to sound non-threatening.
  4. Surprise: Be genuinely interested in learning something new and try to gain a fresh perspective.

Talking About The Weather

Many people hate it when the small talk is of the weather, but fail to understand that it is actually a kind of code that helps people overcome their inhibitions and be ready to actually talk to the other person.

Once the person who has been approached feels comfortable, real talk can happen.

Everyone is interested in a really deep, engaging conversation, but they will not show it, and it is up to us to discover the same.

Listening For A Higher Purpose

Listening can be for:

  • Information
  • What we know about
  • What we want to experience.

We need to work more into the deep levels of listening for motivations, values and feelings.

The Art Of Listening: The Echo

Another way to signal your attentive listening is to simply echo what the other person is saying.


The Stranger says: At that moment, I felt frustrated.

You: You were frustrated.

Why We Don’t Talk To Strangers

The main reason we don’t talk to strangers is simply because we don’t talk to strangers. People are simply not supposed to violate the norm of leaving other people alone at back alleys, parks and subways.

The trick is to acknowledge this handicap and pre-frame the negative thoughts of the other person by reassuring them that you know you are breaking the norm.

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