An Introvert’s Guide to Starting Conversations

Building relationships one word at a time

Lady Jade
Lady Jade
Oct 17 · 7 min read

ntroverts aren’t especially jazzed about confrontation. But, that doesn’t mean we don’t like making new friends or having conversations — it’s just intimidating. Our fight or flight response begs for a few conversation starters up our sleeve to steer us as far away from the awkwardness that could ensnare our future exchanges.

In the past, I’ve looked up “how to start a conversation,” as I didn’t want to ruin the possibility of a good interaction with my awkward glances and jumbled words. The conversation starters I found were always philosophical in the sense that if I were asked these questions, I wouldn’t have a response. If you’re meeting someone for the first time and you ask, “what do you want to do with your life?” they’ll probably feel guarded, wondering why someone they barely know is asking such a personal question. Hence, my hopeful google search ended up being a waste of time.

I love to talk, but I’m also an introvert — I’m a small person with a relatively quiet voice. However, after many attempts at starting conversations (with probably more failures than I’d care to admit), these tips will hopefully help you start your next conversation — awkward-free.

Be Respectful & Aware

When you approach someone, you have to be aware of what they’re doing and who they are. I’m not saying you should bow down to someone if you think they’re higher up the social latter than you — but rather you’d approach, say, your boss differently than your best friend. Analyze the situation and respect the natural boundaries when going up to someone. Being respectful of their time and space will only improve your interaction. If you step over the line in the first few seconds of conversing, you’ll be left with that awful, icky feeling — embarrassment.

Here’s an example: If you’re in a cafe and you see someone you’re acquainted with at the table next to you, be aware of what they’re doing and see if approaching them would be appropriate. If they look at ease simply sipping their coffee and running their eyes across the morning paper, I’d say it’s a safe bet to walk over and start a conversation. However, if you’re both waiting in line to order coffee and your acquaintance is on a phone call or looks miserably anxious, maybe steer clear of them that morning. They’ll be both irritated that another piece of stimuli is distracting them from their busy morning, and they’ll probably be a little embarrassed being in that state of upheaval. So like I said, be aware and be respectful. Reading a situation is almost as important as taking part in it.

Embrace Your Quirks

We’re all quirky people, as humans are undoubtedly weird. Our unique character traits make us exciting and different from anyone else. Sometimes letting yourself trip on your words only highlights your unique personality.

In my own experience, being shy is how I’ve compensated hiding my quirks. If I’m not having a conversation, then I won’t scare people away with my weirdness. After many years though, I realized, “Hey! This is me, and I’m going to embrace my quirks!”. People that don’t honestly care about you and only speak to you when it comes to their advantage won’t talk to you in the first place. They’ll be intimidated by your quirks and will leave the situation themselves. I have to say, avoiding conversations with people like that has only made my life better. Of course, embracing yourself for who you are is an incredibly tricky step and doesn’t happen overnight. Go easy on yourself and take baby steps.

Here’s an example of embracing your quirkiness: If you’re really into science and you notice your friend has suddenly burned their tongue on their coffee, starting a conversation with a tip or even a scientific fact about hot coffee is embracing your intellect and your desire to teach others about the quirks of the world. You’re showing a piece of your personality, which will only benefit you in the long run. It’s a big step — I know.

It’s scary and makes you feel horribly vulnerable — but once you embrace who you are, it’s liberating to be yourself.

If you get a confused response back, move on, and realize, “You win some, you lose some.” On the flip side, if you receive a response that shows genuine interest or gratitude for the new tidbit of knowledge, you may have made yourself a new friend.


Listening is just as crucial as the actual talking. Yes, there’s nothing to listen to if there isn’t a conversation; however, keep your eyes and ears open. Like the first point of staying aware and respectful of the situation, listening to what’s happening around you before you initiate conversation can prepare you for what to say.

For example, let’s say you’re in the cafe again, and you see not one but two of your acquaintances. Before adding yourself to their conversation, listen to what they’re saying. Ask yourself, “What input could I bring to the conversation? What unique perspective do I have?”. Yes, I know these questions sound rather like those of a high school English classroom; however, there’s a reason we examine these kinds of questions. We need to understand what’s going on around us if we want to constructively be a part of it.

Once you have joined the conversation, no matter how many or how few people are involved, genuinely listen. Don’t wait your turn to contribute your opinion; don’t stare off into the distance. You’ll be surprised by what you hear. Remember to keep eye contact, too, as it shows you’re actively listening and paying attention. Direct eye contact also increases empathy and can, therefore, improve the emotional connection in the conversation. Although direct eye contact is nothing less than intimidating, it also enhances your perceived confidence and can improve the overall comfort level of the conversation.

Conversation Starters

Now you’re probably thinking, “Well, okay, I see the three points above, but I still don’t know how to actually start the conversation”. No fear! I’ve created a short list of things you can say if you insist on having a backup. The reason I’ve kept the list short is one, every situation is different. Some things work fantastically in one case, while at the same time, they could be detrimental to another. And two, you’ve freaking got this. You have feelings and motivations, and creativity to contribute! If you’re reading this now, you’ve definitely had conversations in the past. You can do this! Humans have evolved to have advanced communication. As a result, we can now collaborate effectively.

But just in case: here are some universal conversation starters that aren’t incredibly personal and aren’t incredibly awkward. Fair warning: as these are rather generic, they aren’t the most interesting. The general idea of generic conversation starters is to start the conversation and then encourage you to branch off to something more unique afterwards.

  1. “How was your weekend?”

2. “I really like your shirt. Where did you get it?”

3. “I see you’re drinking the new coffee blend. Do you think it’s worth trying?”

4. “Did you hear about the game last night? I can’t believe the Giants lost!”

5. “Do you need help carrying your bags upstairs?”

6. “Do you want to join Joey and I upstairs for a cup of coffee?”

7. “I heard you’re interested in surfing, that’s super cool! Where do you surf?”

8. “Did you hear about the big snowstorm? It’s supposed to be really bad! Do you think we’ll have work tomorrow?”

9. “How was your day? Anything exciting happen?”

Okay, so I know the fake situations seem a bit silly, but showing examples in a generic context shows you how friendly conversation is normal and not something that needs to be awkward. Some people are just unfriendly, and that’s how it goes — don’t expect every conversation to be sunshine and butterflies.

Returning back to the examples I gave above, notice how most of them were questions that could lead to something more. Whether that be an answer that’s more than “yes” or “no” or leading to an action, like helping a co-worker, your conversation is less likely to fall flat. Don’t be afraid to use more than one conversation starter and, of course — read the room. Not all conversations will belong. If it comes to a natural stop, don’t force more words. Try again later when you have something more to talk about.

In The End

Confrontation is mind-numbingly terrifying for some of us — I totally understand. However, interacting with other humans will boost your happiness and improve your social skills — two fundamental aspects of being a person in modern society. Stepping out of your comfort zone can lead to a whole host of opportunities you may not have noticed if you didn’t confront your fears. Next time you’re in a coffee shop and see one of your friends, don’t be shy and strike up a conversation. All it really takes is a friendly smile and a pleasant “Hello.”

The Ascent

A community of storytellers documenting the journey to happiness and fulfillment.

Lady Jade

Written by

Lady Jade

Eighteen • Lean, Mean Writing Machine • Photographer • Music Enthusiast • Avocado Fan • Animal Lover

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join 128,000+ others making the climb on one of the fastest-growing pubs on Medium.

Lady Jade

Written by

Lady Jade

Eighteen • Lean, Mean Writing Machine • Photographer • Music Enthusiast • Avocado Fan • Animal Lover

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join 128,000+ others making the climb on one of the fastest-growing pubs on Medium.

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