An Introvert's Secrets To Creating Great Conversations Without Saying Much

With examples on how to expertly insert them into almost any conversation

It was 10 pm and I was tired. Sure, I had made up this ridiculous challenge for myself but it was only a 3-minute Lyft ride. Maybe I could let this one slide and no one would be any wiser. After all, competitor, referee, and judge were all the same person - me.

You see, I used to be painfully shy but I wanted to teach (and re-teach myself) to learn to overcome that shyness so I could really experience true connection. Part of my self-education was creating social experiments for myself. This one, in particular, involved taking Lyfts everywhere and trying to have an intimate conversation with every Lyft driver I met in a new city I had just moved to.

But meeting strangers is hard. Especially the ones I knew I was likely never to see again. There were days when I really didn’t want to. Like this one.

But it seemed that my Lyft driver wanted to have a conversation. But that didn’t make me want to talk any more than I did before. So, in my true problem-solving manner, I tried to get him to do most of the talking.

With my first question, I hit the spot. He latched on to a question about his passions and the words poured out of him. With each following question, he got more and more excited and I got more and more energized. The 3-minute Lyft ride ended up being two hours long as we sat and talked outside my apartment after the ride ended. In the end, we both walked away feeling empowered and like we truly connected.

That night, I learned how you can say very little and completely change someone’s life or simply leave them feeling on top of the world. Now when I feel tired or especially introverted, I use it to explore what questions or things I say could lead someone to speak more about themselves and really open up.

The two big things I found are 1) It mostly involves generating an emotion, and 2) Creating engaging conversations didn’t actually require me to say anything especially interesting or even say very much at all.

If you are an introvert or someone who doesn’t believe they are interesting enough to date or make friends, I wrote an article with my most effective questions to ask, when they can best be used, and how to easily insert the questions into a conversation.

Read the full article here

I hope it inspires you to go out and make some life-changing connections of your own. I’d love to hear how the questions worked out for you or just about you in general. Get in touch by hitting reply on this email or sending me an email on

If you’re interested in some of the drivers I met while conducting this experiment, read about it here.