Life hack: Conversation starters that aren’t boring

How To | August 21, 2020
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Here’s how to spark a memorable conversation with pretty much anyone.

Small talk can be helpful for when you are first chatting with a stranger or new acquaintance. But if you want to get to know someone—their values, their passions, what drives them—you can’t often gain those insights by chatting about the weather. 

Here are some thoughts on how to spark that personal connection with another human. Keep in mind, it doesn’t have to mean that you will stay friends for life. The goal is to better understand someone’s experience and their perspective on the world, to step for a moment away from the superficial and develop greater empathy. 

Now that many of our conversations are happening online, we also have some techniques for connecting better virtually. 

Listen first

The first rule about a great conversation is to make it about the other person and listen with intention. Sounds simple, but listening is a skill that takes its own kind of practice. Especially in our days of constant stimulation, sharing, and activity, it can be hard to sit back and truly lend an ear. 

If you are more of an extrovert and chatty person, remind yourself to wait (rather than thinking of how to jump in or what to contribute next). If you are more introverted, know that good eye contact, leaning in, and having an open stance (no crossed arms, feet slightly turned toward your new friend), can make you a strong participant even when you are saying nothing. 

The online version: On online conference calls, it’s extra important to wait a beat before stepping in to say something. There is sometimes a delay and it’s better to hear the other person out completely before you take the mic. 

Ask open-ended questions

Some of the lists out there for deep, insightful ice breakers are pretty intimidating. It might not be your cup of tea to jump right into asking someone about their earliest childhood memories or their most searing life regrets.

We’ve compiled a list that is engaging but approachable: not overly personal, while still leading to conversations about dreams, hopes, and ambitions. Feel free to mention inspirations of your own or causes that move you to help get the exchange flowing. 

  • Has anyone inspired you recently?
  • When do you feel most inspired?
  • Who of your idols would you most like to meet?
  • Tell me about a piece of art or a story that resonates with you.
  • What place do you want to go visit more than anywhere else?
  • If you could change one thing in the world, what would it be?
  • Is there a particular cause that you care deeply about?
  • Is there something that you wish more people knew about?


The online version
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It can be even harder to do small talk on a computer screen. First, you are limited by your surroundings and sitting at your own table or desk. It can also be harder to read body language. So why not approach the conversation by diving right in? You can warn the other person that you have a nice set of questions to jump into right away so they are prepped to get started. 

Don’t be afraid of the 7-minute lull

It happens to us all. That awkward moment when no one is saying anything. There are theories the average conversation topic can’t sustain much longer than the 7-minute mark. Whether or not that’s true, we’ve all experienced the conversation pause. Don’t worry, it can be a good thing when trying to get someone to open up to you. 

Silence can incite thought and might spark a new idea from the person you are speaking to. A person may want to fill the air by telling you more about themselves. Still, if after a few moments, you are still experiencing the sound of silence, you can add another question to the mix. Maybe something more lighthearted and whimsical, like:

  • So what do you think about how the [local sports team] is playing?
  • Are you more of a Rolling Stones or a Beatles fan?
  • Got an unusual talent? 
  • Would you rather have one horse-sized duck or 100 duck-sized horses?

Exit with grace

You have done all the things, are feeling like you have learned something new, or maybe are just ready to exit for a mental break. A good way to close things might be: “Thank you, [insert name]. It was great to chat with you about [insert topic]. I will look into [reference a topic you discussed]. I am just going to go [refill my drink / say hi to the host / check out the view].”

The online version: The beauty of chatting from home is that there is more flexibility in how you bid adieu. On a conference or zoom call, you can still mention that you need to get up and get a glass of water, start making dinner, or take care of things around the house. 

You can also admit you have had a lot of screentime and need a break. It’s so relatable these days that no one will fault you for it. Just don’t forget to thank your conversation mates for taking the time out of their day to chat with you. 

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