The Stranger On The Subway: Asking Questions - Deepstash
Conversation Starters

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How to ask open-ended questions

How to avoid awkward silences

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Conversation Starters

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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.


4.41K reads


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 s...


7.53K reads

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.
  • On...


8.39K reads

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.


5.44K reads

Doing Conversation Starters Differently

  • 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 an...


6.08K reads

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.


14.7K reads

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 c...


5.61K reads

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 conversat...


5.97K reads

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 ...


4.95K reads

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.


5.28K reads

Talking About The Weather: One Of The Most Common Conversation Starters

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...


6.41K reads

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...


5.78K reads

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 no...


4.52K reads




Stashing about leadership and communication. Avid reader.

Conversation starters to connect with anyone you meet.

Related collections

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5 Keys to asking better questions

5 Keys to asking better questions

Asking a lot of questions (lots but not too many) unlocks learning and improves interpersonal bonding.

  • TYPE 👉 People interacting with a partner who asks lots of follow-up questions (solicit more information) tend to ...

Asking deep questions

Once you have got the chance to get to know a bit more about the other, you can initiate the use of deeper questions. 

These allow you to create a bond and to show to the other person how interested you are in his or her life.

Know where you stand on the introvert-extrovert spectrum

Know where you stand on the introvert-extrovert spectrum

  • If you’re an extrovert and find yourself talking too much, try to shift the focus on asking more questions. 
  • If you’re an introvert, ask yourself whether you’re speaking enough and giving the other person enough information about yourself to help them feel connected to ...


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