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Small Talk: 10 Exciting Tips To Start A Memorable Conversation With A Stranger

Talk to any stranger with ease whether in the streets, online or anywhere else.


Great oaks from little acorns grow or so goes the saying. This goes too for meetings with strangers. A small casual talk with a random person you meet in the streets, boardrooms, dinner parties, or in some cases on social media can snowball into something exciting, a lifelong friendship, a business partnership or a life partner. Just sit back and imagine how you met your most cherished friends today, how you hit it off and what exactly you said to them on your first meeting that had such effect on them to make them want to stay in touch with you over the years. You must have made quite an impression on them to win their admiration (otherwise how would they have stayed?)

It goes without saying that not every casual conversation with every stranger we meet in the streets will blossom into friendship, but if you are ever going to make anything of such unplanned and spontaneous meetings, you’d have to master the art of conversation as I would like to call it (Knowing exactly how to break the ice and start off a conversation with a stranger that would be truly memorable by any standards).

Those who have mastered this art have gone on to acquire the finesse to talk to anyone anywhere with ease. The benefits have been monumental, from a wide social circle, to an ever growing lists of contacts spanning different countries with the ability to resolve any issue with just one call (You could only accomplish these only by knowing a lot of people in high places)

Once you master the tips to be shared here, you’ll become more outgoing, talk with less tension and rack your brains less for any amazing one-liner that would win the admiration of your listeners. It would also mean docking less from the familiar sight of strangers or precipitating your departure at important social events. Your conversations with strangers will become less abrupt, less stilted and livelier. Now that I have attention, here are 10 tips to help you start a memorable conversation with a stranger anywhere and with aplomb.

(1) Be In A Relaxed Mood

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Nothing zaps the life out of a conversation more than tension. Conversations are best when they are spontaneous and without forethought. You have to think up things to say on the spur, picking up hints as you go along. But sometimes, we worry such much about not having planned what to say well in advanced and that this takes the fun out the small talk often leading to considerable discomfort.

Don’t walk up to people timidly and attempt to start a conversation. It’s creepy and you might be seen as more a nuisance. Instead, wear a disarming smile, with a friendly body language and posture. This will make the other person very comfortable and the conversation will be fun right from the start.

(2) Be Very Confident

One of the reasons people are afraid of going up to strangers is self-doubt. Some of us fear rejection, often we worry about not being accepted by the other person. Thoughts rooted in self-doubt often crisscross our minds leaving us dead in our tracks. We have thoughts like “what if they don’t like me?”, “what if they think I’m stupid?”, “what if they aren’t interested in a conversation?” But you should dismiss such thoughts outright from your mind – what really matters is being confident as you start that conversation, if however you notice that the person on the other end isn’t interested, then you should walk away. Don’t make such a big deal out of it. It could just be that they are in a bad mood, or something else is going on in their lives that day, not necessarily because of something wrong with you.

(3) Be Observant

One of the most effective ways to start off a conversation that actually interests a stranger is to be observant – it also reduces your bounce rate. Before you approach anyone for a small talk, you have to pause a few seconds, gaze their direction and gauze them for important clues that can act as the perfect conversation starters. You have to establish a connection with them the moment you open your mouth to say anything, and the only way you can initiate this is through observation. Pay attention to them, find anything striking about them, their appearance, the clothes or shoes they are wearing. Also observe the context in which you are approaching them, like where the conversation is taking place, is the stranger having something about them that denotes a common interest. Are they reading anything you’ve read and enjoyed, or honestly want to read?

(4) Make A Statement

Well, if you’ve fully internalized the previous point on picking up clues then it’s a whole lot easier kick starting your conversation with the stranger. Usually in getting started, you can take either of two options available.

You can start with a compliment

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Starting with a compliment does have its own finer points. If you’ve read Dale Carnegies go-to book on making friends; How To Win Friends And Influence People, you’d already know that one of the greatest motivations in human nature is the desire to be appreciated. When you offer someone genuine compliment, it tells them you are genuinely interested in them and does pave the way for an exciting conversation. But give honest compliments (followed by a question) by finding out one thing about them that you consider noteworthy – “Hey nice shirt, where’d you get it?”

Or Make an Introduction

If you decide you’d rather not take the route of compliments, then you can as well introduce yourself to the stranger – more like cutting to the chase. Say something like “Hey, can I talk to you for a minute?” or “Hello, I’m Peter”. You can then wait for a response from them. If they do, then you might continue by asking them about themselves and then listen “Do you love sports?” Based your questions on the particular context, a question like the one above would be inappropriate for a conversation for place like the library or art gallery.  You can ask them about their opinion on something you want to purchase assuming you are at a mall or restaurant. Yep, nobody likes being in conversations centered on the other person (it’s the most annoying thing ever!).

(5) Listen Up For Clues

Be attentive and observant and listen up for clues. If the individual is unresponsive or uncomfortable, then you are better off leaving them alone. Any further persistence would amount to harassment. But if after you’ve made your statement, you have a positive response then the next thing you should do would be to follow this up with a question about their interests “do you like sports?” and get them talking.

(6) Have A Sense of Humor

Crack some jokes mostly self-deprecating ones usually this puts your listeners at ease and gets them talking.

(7) Avoid Sensitive Topics

Avoid discussing sensitive topics with strangers you are meeting for the first time. They will find you rather creepy and this can act as a turn off. Equally, they can often lead to heated arguments which can create a lot of negative air around you and the stranger with the result that your conversation ends on a terrible note. Talk less about race, politics, religion, or the best sports team in town.

(8) Avoid Asking Generic Questions.

Don’t ask strangers generic questions as they would often provoke a “yes” or “no” answer – they can lead to a dead end and bring the conversation to an embarrassingly abrupt end.

(9) Exchange Contact Information

This is something that if overlooked would mean the entire conversation was a waste of time. If your conversation went very well with the stranger, you’d want to stay in touch with them and that is precisely why exchanging contact information with strangers is so important. So once you realize the conversation is coming to an end, as all good things do, then ask for their contact information but if they seem hesitant, then give them yours. An email address would be equally just fine.

(10) Have An Exit Strategy.

You can’t expect your conversation to go on forever, so it is important you know how to bring the conversation, however interesting, to a convenient end. You can choose to go back to find your friends or simply tell the other person you’ll like to grab a bite. Alternatively you can say “I’ve got to run, it was nice meeting you Jane (or whatever their name is)”.

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