Connecting with Strangers: Tips for Shy and Reserved People

Connecting with Strangers: Tips for Shy and Reserved People

I went on a short, but much-needed getaway recently.  While sitting in my seat on the plane wiggling my toes in my new sandals, a goofy smirk spread across my amused face as I distanced myself from the cold snow and thought of the warm sunshine ahead.  The sunshine, apparently, has a different effect on people than the prolonged dreariness of gray skies and chilly air.  Everywhere I went on my trip, people smiled and said hello.  Perhaps tucking the daily worries in the corner of my mind instantly made me more welcoming of conversations with strangers, or perhaps people are just naturally happier and more approachable with a good dose of vitamin D in their life.  In any case, I learned a valuable lesson.  Exchanging warm hellos and quick chats with strangers can create a lasting footprint on your heart, even though you’re likely never to see that person again.  There is something sacred and inspiring about having a chat with someone, saying goodbye, and not expecting to ever see or talk to them again.  It can lead to some interesting, candid conversations that can be tucked in the depths of your soul for future retrieval.  We may not remember details of each conversation with a stranger, and many will likely be forgotten.  Yet each interaction like that creates a small connection in the moment, and over time, fills your soul with a deeper connection to the world.

Of course, approaching a random stranger and asking them to open up can be scary and weird for both sides, so here are a few tips on how to approach new people, and what to say to them.

Focus on embracing the simple connection with someone, and don’t expect to become friends with the newly acquainted stranger.  You don’t even have to exchange names or phone numbers.  Each genuine encounter with another human being can be its own experience, a little footprint on your heart, allowing your soul to fill up with joy and warmth.  If the person you approach suspects you want something from them, whether it’s friendship, a relationship, an introduction to someone else…it can alter the authenticity of your interaction.  Those conversations are best left for networking.

Ways to create a connection with a stranger

  1. Be considerate of people’s time and personal space.  Rather than cornering someone who seems to be in a hurry or is deliberately avoiding eye contact, look for opportunities to chat with someone who’s relaxed, and maybe even offers a quick nod as acknowledgement of your presence.
  2. Do a quick analysis of the person’s energy and mood.  It’s ok to approach someone who’s visibly in a bad mood or having a bad moment, just do it without any preconceived judgment about the person’s behavior or personality.  We all have moments that we wish we could take back, moments that don’t define us, but are a mere snapshot of a single reaction to something in our lives.  Use this as an opportunity for a compassionate, humane interaction. A simple hey there, you seem frustrated, I hope your day gets better, can be validation enough for someone that things will, indeed, turn around.  Or try to diffuse the negative energy with a joke or a funny jab at yourself.  It just might snap the person out of their funky mood and get them to chuckle.

  3. What if they don’t engage?  If you get the cold shoulder, or a weird look, just keep on moving or resume what you were doing before.  Most importantly, don’t take it personally and don’t pass unfair judgment.  Not everyone will be in the mood to respond to a stranger, some people may be too socially anxious, others may be too lost in their thoughts. Think of the moments you don’t want to talk to anyone, we all have them, so just be accepting and respectful of those moments.

  4. What if they laugh at me, roll their eyes or get angry and tell me to leave them alone?  Hey, we get it.  No one likes to feel embarrassed, and approaching a stranger makes you vulnerable to embarrassing situations.  Take a deep breath in, and exhale slowly.  As you exhale, give yourself credit for reaching out to someone and allow the interaction to end there.  Don’t let someone else’s negative reactions to their own experiences influence your thoughts.

  5. I said hello, now what? It can be hard to predict what comes after the “hello”, because you don’t know how the other person will respond.  However, with a little preparation and observation, you can set yourself up for success.  

    • Observe your surroundings.  Is there anything interesting happening that you can comment on?  Are you both staring at the same products in a grocery store aisle?  You can also comment on the weather, as cliche as it may seem, it’s always a good opener to small talk.     

    • Take a moment to notice something interesting about the person that you can compliment them on.  A genuine compliment about a person’s skill or accomplishment can have a lasting effect.  But even a compliment about the person’s appearance, or what they’re wearing, can leave them feeling uplifted for the rest of the day.  Be careful though not to mask a criticism or correction in a compliment, it can leave the person feeling confused or even offended.  For example, while walking down the street one day, wearing bright cyan blue jeans and a black shirt, I felt stylish and proud that I pushed my confidence outside my comfort zone and dressed my curves in bright colors.  A woman stopped me and said she loved the colors I was wearing…I was beaming, she had just made my day.  Only she proceeded to add that she was a fashion designer, and suggested I swap the colors and wear black on my round curves and bring the blue up to my face to “compliment my complexion”.  And just like that,  my sense of confidence turned to a walk of shame that burned within me for the rest of the day.  So when you’re giving a compliment, stop at the compliment unless your professional input is requested.

    • Take a few moments each morning and read a few interesting headlines or articles.  You don’t need to remember all the details, just enough to throw out a comment.  At the least, you’ll get a quick response like “oh yes, I heard about that,” or you may get someone engaged in a conversation.  Oftentimes, people like to share their opinions on current events and just want a listening ear to let them share their input.     

  6. Let the conversation, or lack thereof, flow and end naturally.  Some interactions will be very brief, some may even end at hello.  But others may turn into memorable conversations as you realize how much you have in common with a complete stranger.  While on my little getaway trip, I was walking through a beautiful arboretum park, mesmerized by all the local trees and plants.  Totally in my own zone, I heard a woman say hello and comment on the interesting palm trees.  We started chatting about all the plants we couldn’t identify, and in our conversation we learned that not only were we both on vacation, but that we were also from the same state, and better yet, neighboring towns.  I never learned her name, but my heart beamed with joy the rest of the day, which opened my mind to more conversations with interesting strangers.

  7. Be kind to yourself.  Unless you’re a natural conversationalist, talking to people can be very draining.  Your energy may even dip just thinking about and preparing to talk with someone, and you may feel like you need a vacation afterwards to destress.  That’s ok, accept that may happen and take the time you need to recenter.  If a conversation doesn’t go well, don’t beat yourself up over it and don’t dwell on it.  Take a moment to breathe and allow your thoughts to settle.  With practice and repetition, it’ll become more and more comfortable.

Do you have other tips on how to strike up a conversation with a stranger? What has and hasn’t worked for you?  

Get the HinT Challenge

Introduce yourself to one new person each day for a month.  It’s ok to start with people that feel familiar to you, but with each new day and new introduction, push yourself a little more beyond your comfort zone.  Say hello to people who look, talk, and act different from you, and be genuine about getting to know their story.

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