5 Hacks to Turn Small Talk Into More Meaningful Conversation

Very few people actually like small talk. It can feel forced, shallow, and inauthentic. At its worst, it feels as ridiculous as this exchange between Tracy Jordan and Kenneth on the popular TV show 30 Rock:





Introverts especially tend to loathe small talk—but it’s not because we shun connecting with others. “Let’s clear one thing up: introverts do not hate small talk because we dislike people,” explains Laurie Helgoe in Introvert Power: Why Your Inner Life is Your Hidden Strength. “We hate small talk because we hate the barrier it creates between people.”

Introverts would, by definition, rather talk about something meaningful.

If only we could skip the pleasantries and dive right into deeper conversation. Unfortunately, “few relationships go from handshake to heart-to-heart in the space of one conversation,” writes Michaela Chung in Alone But Not Lonely: 7 Steps to True Connection for Introverts.

However, there are some things you can do to speed the process along. It’s all about asking the right questions and being willing to share some personal information about yourself. Try these 5 hacks to start more authentic, interesting conversations:

1. Get the other person to tell a story.

One reason small talk is boring is that we often ask questions that can be answered in just one or two words. Instead of asking, “How are you?” try something more open-ended, like, “What did you do today?” or “What was the most interesting thing that happened at work today?” Questions like these invite the other person to tell a story.

Here are some more ideas from Chris Colin and Rob Baedeker, authors of the book What to Talk About: On a Plane, at a Cocktail Party, in a Tiny Elevator with Your Boss’s Boss:

Instead of…

  • “How was your day?”
  • “What line of work are you in?”
  • “How was your weekend?”
  • “What’s up?”
  • “How long have you been living here?”


  • “What’s your story?”
  • “What’s the strangest thing about where you grew up?”
  • “How’d you end up in your line of work?”
  • “What was the best part of your weekend?”
  • “What are you looking forward to this week?”
  • “Who do you think is the luckiest person in this room?”

2. Be curious.

As an introvert, you’re probably naturally curious. You wonder how the world works or what makes a person tick. When talking with others, you can channel your natural curiosity and avoid small talk. Put yourself in the mindset of being curious to learn more about the other person. You’ll listen more intently, your body language will show that you’re engaged, and you’ll naturally think of questions that move the conversation forward. Being curious about others is a highly attractive quality, and it creates immediate interest and intimacy.

3. Ask why instead of what.

This is a twist on asking open-ended questions. Instead of just asking about the facts (“what” questions), ask people why they made certain decisions, suggests The Date Report. For example, after you’ve asked, “What college did you go to?” follow up with, “Why did you choose that college?” Hopefully this results in an interesting conversation in which you learn a little more about what makes the other person tick.

4. Share details about yourself and see what sticks.

This can be hard for introverts, because we tend to dislike talking about ourselves. It puts all the attention on us and we feel exposed and vulnerable. We usually don’t open up until we know someone well and feel comfortable around them. But inevitably, this means we get stuck in cycles of mind-numbing small talk in which we don’t reveal anything about ourselves and in turn, we don’t learn anything meaningful about the other person. The relationship doesn’t grow in a satisfying way, because it lacks intimacy.

Another way to avoid mind-numbing small talk is to share a few details about yourself and see what sticks. If you work in an office or go to school, you probably get asked the questions “How’s it going?” or “How are you?” several times a day. Instead of giving the typical response (“I’m fine, how are you?”), expand on your answer. Give a few details about your day. You might say something like, “Good, I got up early this morning to jog on my favorite trail. Now I’m feeling great!”

However, don’t make the mistake of oversharing. You shouldn’t launch into a 15-minute monologue about your latest existential crisis or discuss all the possible causes of your this morning’s indigestion. These conversation topics would be more appropriate with a close friend, not a work or school acquaintance.

When you share details about yourself, notice how the other person reacts. Do they keep the conversation going by asking a follow-up question (“Cool! What’s your favorite trail?”), or do they give a disinterested nod? If the other person doesn’t seem interested, try revealing another detail about yourself until you hit on a topic that gets the two of you talking.

5. Dare to be honest.

We often sacrifice expressing our true thoughts and feelings for the sake of politeness. But there’s something very authentic—and surprisingly charming—about being completely honest. Chung writes that you can quickly take conversations to a deeper level by saying things like:

  • “To be honest, I don’t go to parties very much. I feel pretty overwhelmed being here.”
  • “I’m not a big talker, but I like listening.”
  • “I don’t like camping. Like, at all.”
  • “I’m really proud of that.”
  • “This feels awkward.”
  • “That hurt my feelings.”
  • “No. I don’t want to go. I’d rather stay home and have some me time.”

Of course, don’t take this to the extreme. You risk alienating your conversation partner if you overshare or insult. However, if done right, even one authentic admission quickly builds intimacy, because honesty draws people in and makes them let down their guard.

I hate having to do small talk. I’d rather talk about deep subjects. I’d rather talk about meditation, or the world, or the trees or animals, than small, inane, you know, banter. —Ellen DeGeneres  

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Read this: 21 Undeniable Signs That You’re an Introvert


  • I’ve always found No. 1 to be the best way for me to make a conversation more meaningful. And a lot of people have such cool stories to tell. Now if I could only find the courage for do No. 5 more often!

  • Dok Woods, Author says:

    My answer to the inane question, “How you doing?” is always “FANTASTIC!” That provides a whole new line of follow up conversation.

  • I need to remember this. As an introvert, I can talk with someone for ages and yet never reveal anything about myself!

  • Kanade says:

    This is awesome. Finally I know how to skip inane questions.

  • Paul says:

    This is really good advice. For those who have trouble starting with small talk in the first place, please read my latest article on the topic here: https://getthefriendsyouwant.com/how-to-make-small-talk/

  • So happy I stumbled on this.it’s what I needed to read. Look forward to future emails.

  • My favorite, go-to question is always, “What are you passionate about?” If the other person doesn’t spark about something (*anything*), then I lose interest in chatting. When they give an answer, I do my best to relate it to something I love, too.

  • As an introvert newly into the dating world, I’ve been googling strategies for small talk. I’m so glad to have found your article. I’m looking forward to hearing more from you. I’ve also cross posted this to my blog as well.

  • Tval says:

    Two what-if’s that come to mind…What if there IS nobody to talk to because everyone’s already talking to someone else, and engaging in a conversation would involve either butting in or standing there awkwardly waiting for a conversation to end – ? And, what if someone I attempt strike up a conversation with…doesn’t want to talk to me? Some people are just stuck-up that way.

  • Scia says:

    I think I’ll mention that it’s okay to adapt your strategy to fit your preferences. Some of these example questions would feel too probing to me and I would freeze if asked them. But the general principles are adaptable. For example, maybe instead of “What are you planning on doing/looking forward to?” you might ask “What kind of things do you like to do for fun?”