3 Easy Ways To Connect With Absolutely Anyone

Tips from the country’s most interesting tour guide

Photo: Tony Anderson/Getty Images

Why are people sometimes so unspeakably boring? Here’s a secret: They aren’t. You just have to be interested in what they have to say. I’ve learned this during my years as a cult-favorite (hey, they say it, not me) tour guide, documentary subject, and story spinner. And I know that with a few guidelines, anyone can create interesting, dynamic conversations.

Being a tour guide doesn’t mean that I’ve always found talking to people to be easy or natural. Here’s how I think of it: I once heard an interview with musician Elvis Costello in which the prolific songwriter explained that he is actually that not good at playing the guitar. He considers himself to be the opposite of a virtuoso. His original songs derive from the fact that he is in a constant state of desperately reaching for notes, doing his best to simulate what he would play if he could.

I became a tour guide for a similar reason. I’ve always loved history and the city, and I love walking around city streets, navigated by my own inspiration and a continual prioritization of beauty. Attempting to make city history come alive for a family from Kansas City and the couple celebrating their 50th wedding anniversary who just got in from Wales who are sitting right across the aisle from the family from Kansas City — it’s an inherently awkward situation and very likely to inspire some awkward conversation, or lack thereof.

Here’s the key: You have to train yourself to be interested in people. This can be an art and a martial art. Once you’re interested in people, they’re going to be interested in you, too — and conversation will flow. Now, after years of practice, I have a system for creating connection with anyone:

Share personal myths

RuPaul once said, “Everybody has to bring something to the birthday party.” It helps to bring a core story to a conversation, to have on deck a personal anecdote that lets a new acquaintance know everything they need to know about you. This isn’t a rehearsed tale; it should feel alive and frenetic in each of its retellings. Because, after all, that’s what a myth is: a story that humanity retells over and over, throughout the generations. Your personal myth is doing just as much as Iphigenia’s. And it’s a great conversation starter.

Once you share yours, people will share theirs — and that’s how the conversation will open up. Each retelling of a myth is a hot and fresh delivery from the human condition.

Appreciate beauty

Next, lean into your ability to appreciate beauty. Taking a walk with someone, or even sharing a virtual museum tour, isn’t all that different from a guided tour from a professional: Both are opportunities to appreciate beauty together.

Voltaire observed that the act of appreciation has the magical power of incorporating whatever we’re appreciating into ourselves. Likewise, as we are appreciating the beauty of the world together, we’re also working out the muscle that appreciates the beauty of ourselves and each other.

We’re all interested in seeing something great. This is true in everyday interaction as well. If you want to get people communicating, look at something together — it can lead to a deep sharing and a feeling of collaboration. We’re all co-crafting this unfolding reality. Are not most situations co-written? As ee cummings wrote, “It takes two to make a really beautiful mistake.”

Look at things together

Aside from giving my own walking tours on the streets of New York City, I also have given tours at Radio City Music Hall. It was a way to tap into that otherworldly mix of international visitors who are constantly flowing through New York City.

Often, I’d find myself giving a 75-minute tour to a group of people who don’t speak English. But believe it or not, we’d still have a great and memorable time. By imagining what they’d like to see, I’m opening myself to their experience of the world — and just like that, I’m invested in their reality.

At the end of the 75 minutes, the goodbyes between me and my non-English speaking guests are often quite emotional. Deep down, perhaps, we know that we just lived out the most successful, albeit, short human relationships of our lives. We didn’t have time for anything else.

In the end, if you’re interested in a person, then nothing about them is boring. After months inside and in our own worlds, it’s worth making an effort to practice the art of being interested.

speed.levitch@gmail.com//actor, writer & tour guide//films include “The Cruise”, “Waking Life”//travel show: “Up To Speed” on Hulu//book: “Speedology”, 2002

Sign up for The Forge Daily Tip

By Forge

A quick morning email to help you start each day on the right foot. Take a look.

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store