As an introvert, I hate small talk.  It feels awkward and sometimes, even a bit forced.  But I love deep, meaningful conversations.  That’s when I truly start to feel connected to the other person.  However, as an introvert, it can be tough to get past that small talk phase.

Over time, I discovered a little secret – listening.  With any conversation, the most important part is to actually listen to the answers.  Talking is important as the conversation shouldn’t be one sided, but listening is even more important.  Woo hoo!  As an introvert, listening is something I excel at!

I feel like I need to clarify that point a little – the key here is ACTIVE listening.  Think about what the other person is saying.  Sometimes people ask a question and are coming up with their own answer in their head.  Or even worse, their attention is distracted by something else.

Here are six ways that introverts can connect to other people through conversation:

#1. Have conversation starters.

Have you ever been in a social situation where you WANT to talk to the person beside you, but you have NO IDEA of what to say? Conversations starters might be just what you are looking for.  You can use these starters with both people you have just met or even with acquaintances you haven’t connected with yet. 

Here are a few sample conversation starters:

  • What changes have you seen in this town/workplace over the years?
  • What tv shows have you watched lately?
  • What are your plans for the weekend? Summer? Holidays?
  • Great sweater/purse/shoes! Where did you get it?
  • What are you looking forward to this weekend?

#2. Follow up by asking open ended questions.

Open ended questions are great ways to make conversations more meaningful, which in turn, lead to meaningful connections.  Open ended questions help to keep the conversation moving, as opposed to questions with a yes or no answer.  If you can, try to ask specific questions, as they let you control the focus or direction of the conversation. 

Start the conversation with a statement and then ask your question.  Otherwise, it might feel more like an interrogation.  Here are some examples of open-ended questions you could ask: 

  • I grew up in <insert name of town or city>.  Where did you grow up?  (See point #3 as an example of how you can use this question to move toward a more meaningful conversation and connection with the other person).
  • I recently read <insert name of blog post or book>. What’s the best thing that you have read recently?
  • Did you see what the latest lottery jackpot is worth? What would you do if you won that much money?
  • I love to travel. Where do you most want to travel, but have never gone before?
  • I love to watch sci-fi. Do you prefer Star Wars or Star Trek?  Do you prefer the original Star Wars/Star Trek or the newer movies? 

#3. Try to find something in common with the other person.

I grew up in a small community of 50 people and I moved to Toronto after I graduated university.  When I meet someone, I sometimes ask them where they grew up.  I give myself pretend bonus points if the person also grew up in a small town! 

From there, I could talk about how they felt when they moved to Toronto or the Greater Toronto Area, the similarities or differences between our small towns, or how often they go visit their home town.  This is a great way to strengthen our connection to each other. 

#4. Move the conversation deeper by going first.

If you want to get past the small talk phase with people you already know, then I encourage you to gently start the next phase.  Yes, that’s right – don’t wait for the other person.  You can move the conversation to become something more meaningful.  This works especially well with people you have already started to connect with. 

Start by sharing something that shows your vulnerability.  Nothing deeply personal or dark.  When you share something personal, the other person is likely to reciprocate, due to the law of reciprocity.  The law of reciprocity says that it’s in human nature to do something nice in return when someone does something nice for you.  So, go first and the other person will follow.

#5. Share good news.

It can be hard to share good news because you don’t want it to look like you are bragging or that you are arrogant.  But I love hearing when something good happens to my friends.  I genuinely feel happy for them.  So, go ahead and share good news!

In turn, ask other people for their good news.  Celebrate it.  As Oprah Winfrey said, “The more you praise and celebrate your life, the more there is in life to celebrate.”  When you get in the habit of celebrating good news, it will seem as if there is even more good news to share. 

#6. Practice your social skills on strangers.

This may sound a little strange, unless you are an introvert who is shy (see my blog post on Top 8 Myths About Introverts).  Not all introverts are shy, but some of us are, including myself.  By talking to strangers, it’s a way to desensitize yourself to being shy and as a way to build social skills. 

Start by saying hello when you pass someone on a nature trail, comment on the weather (okay, so I threw up a little in my head as I wrote this, but it works!), or even a “Aww, so cute!” if the person is walking with a pet or a small child. 

There are all quick, easy things to do.  And because there is a stranger, there’s no pressure – if you screw up, no one will care.  Best case scenario, it gives you and the other person something to smile about.

Here’s a quick summary of the points mentioned above:

  • Actively listen to what is being said and follow up with questions.
  • But too many questions can feel like an interrogation.
  • So, share more than you ask (a.k.a. more statements than questions).

Do you want an easy way to remember over 100 different conversation starters? If so, then check out these 102 Conversation Starter Cards! They are so simple to use – simply download and print!

102 Would You Rather Conversation Starter Questions - Now Available on Etsy
102 Would You Rather Conversation Starter Questions – Now Available on Etsy

What’s your favourite way to connect to other people?

Until my next blog post, here’s wishing you lots of joy and happiness!

With love,


Hi! I'm Joanne. I’m a Canadian Chartered Professional Accountant (CPA, CMA). Money management is a life skill that I passionately believe all people need to learn. As an accountant, I love helping people understand numbers and money. At BuildingJoyAndHappiness, I share my tips to money management and make understanding finances simple.

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