How to befriend anybody (even if you’re an introvert)

create a spark

I am a journalist and an introvert.

My job requires me to talk to a lot of strangers—including, sometimes, strangers who don’t want to talk to me—and my very nature dictates that I’m often perfectly content to keep to myself.

The challenges and pleasures of being forced into conversation with people I might not have much in common with has taught me a lot about befriending people in everyday life, and meeting new people has become all the more enjoyable for it.

The secret to befriending anybody? It’s not so secret: you just have to ask questions.

We introverts typically don’t require large groups of friends to feel happy and fulfilled. In fact, many of us prefer to have a handful of close friends and wouldn’t be sad if we hardly ever went to parties.

But what many of us do value is having meaningful conversations and making one-on-one connections. You can have those connections with almost anyone you meet, and you don’t have to suffer through small talk to do it.

Good conversation is a skill that can be learned. Before an interview, young journalists often will come up with a list of questions written perfectly neat in fresh notebooks and will cling to those notebooks for dear life, hardly straying from the order of their list. But the more interviewing experience they get, the more comfortable they become having conversations that flow naturally and asking smart follow-up questions.

As I’ve developed those conversational skills, I’ve gotten better at listening and picking up on the things that people will open up about, if asked. I’ve seen people’s eyes and body language become more engaged and less defensive by showing my genuine interest and endearing myself to them. You know what always does that trick? Asking someone to explain what they do: Not just “what do you do?” but “how do you do that?”

A few simple questions to keep the conversation going:

  • What do you like to do?
  • What is that like?
  • How did you learn to do/become interested in that?
  • That sounds challenging. (Not a question, but a good way to get someone to elaborate on the challenges of their work or hobbies – everyone thinks their job is hard.)
  • How did you two meet?
  • I’ve been meaning to check out new [books/restaurants/running routes]. Do you have any suggestions?

Of course, the more you talk to someone, the more specific-to-them questions you can ask!

If you assume the mindset of an interviewer, at the very least, you’ll learn something interesting about whoever you’re talking to, and chances are, they’ll automatically warm up to you. And if you’re talking to an equally thoughtful person who reciprocates the interest, you’ll have an engaging two-way conversation that you both can get something out of—possibly even friendship.

This method is good for anyone, and introverts especially will love this style because it puts the focus on the other person and on having a genuine dialogue. You’ll come off as outgoing and engaging by simply asking questions.

What tips do you have for making friends? What are some of the most surprising connections you’ve made as a result?




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  1. As a reporter myself, I can definitely vouch for this! Asking questions, taking an interest in someone else, is definitely a great way to get to know people. I think trying to go to new places, do new things and generally getting out there helps, too. And of course, stealing your current friends’ other friends. That’s an effective strategy. 😉

    • Cassie Paton says:

      Haha! Yes to stealing your friends’ friends. It helps that I moved to a new city to become a journalist, because it’s put me in so many situations where I have to get out there! But even if I stopped doing journalism tomorrow, I’d do the same.

  2. Love this. I’ve learned sometimes you have to be comfortable being uncomfortable. 😉

  3. So simple but so true! This has definitely been my strategy over the past few years as I’ve moved to new cities and started my own business. I’m extremely introverted so it can be hard to motivate myself to get into uncomfortable situations, but I’m always thankful I did!

    • Cassie Paton says:

      Nothing like moving to a new city to push you out of that comfort zone! And it’s almost always worth it when you do, right?

  4. I’m very similar, very introverted until you get to know me then I’ve been told i’m quite the chatterbox. 🙂 I think asking certain questions like “what are you working on?” and “what are you looking forward to in the next few weeks/months?” – it’s good to see that you’re acquiring success in your field even though you’re an introvert. Git’R’Dun! Have a great one Cassie ! -Iva

  5. Brilliant post Cassie, thanks for sharing! I find that if I’m forced to small talk I won’t be myself, I’ll be this shell I know can get on with people superficially if I have to, so I try and talk about what people are interested in. Or lead in with something off the wall to relax the mood.

  6. Love this! Always helpful to have a few questions to have in rotation, I read an article about being polite recently and the author said the same thing about using the “that sounds challenging” line, it draws people in and endears them to you. As always thanks for the stellar introvert advice!

    • Cassie Paton says:

      So glad you enjoyed it! I’ve realized I could and should write more about introversion, because I have a lot of thoughts about it. There’ll definitely be more posts like this.

  7. I think I am becoming more introverted as I get older. I am far more content to stay home than go out. I like to go through my day and then come home. I don’t want to stay after work chatting or sit in the library for hours studying (although sometimes I do just to feel like I’m getting something done). Those questions are helpful as I have to do an interview Tuesday and needed a few more for my list.

  8. This is great stuff! I do the same, and ask many questions about their life, and when something I know a little about crops up, I’ll insert a little something that I know about it, and sometimes you end up finding common ground on a lot of things. I also try to pretend that I’m talking to my dearest or closest friends sometimes. I’ll open up to them about little things that I wouldn’t normally, because it makes the situation more comfortable and less stiff. This is totally making me want to craft a blog post of my own about this now, haha. Thanks for the great read!

    • Cassie Paton says:

      That is definitely a good technique too, and I’ve sometimes found myself doing the very same with people I think I could truly be friends with if only one of us initiates the conversation. It’s such a good feeling when you make a true connection with someone like that and walk away with a new friend!

  9. This is brilliant. I haven’t done the actual “journalist” thing in a good year so this was a great refresher on how to talk to people you don’t.

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