I’ve moved to many different cities and the first thing I do is head to the cafe. That’s my starting point. There’s no right way for how to meet people in a new city, but you can increase the odds of getting off to a non-lonely start. The cafe as a starting point works for me because I need to set up some normalcy. I wanna become a regular at as many places as I can and focus in on those locales till I’m recognizable. Slowly I start to learn the baristas’ names. Then I begin talking about my work so they know what I do. I ask questions about the city and if they have any recommendations. Then I sit and drink coffee. I say brief “hi’s” to some of the people around me to plant a few seeds. 

Like when I moved to Los Angeles…

One day I was sitting next to a big dude who was on his phone from the time I sat down talkin about deal after deal. 

“Whattaya working on?” I finally said.

“Duude. Everything.”

Turns out he was a casting director but used to play college football. We chatted for a bit and got to know each other. Then I fucked up. I knocked my coffee all over his laptop and it broke immediately. 

He was scheduled to fly to Chicago in like an hour and now everything on his laptop was gone. In a surprisingly calm fashion, he told me to “fix this” and he went off to his apartment to get ready for his flight. He gave me his address. I floored it to the Beverly Center and bought him a brand-new Mac and went to his apartment and was like: 

“Dude, I’m so sorry,” and I gave him the new computer.

He looked at me and was like: “99% of people wouldn’t have done that. You and I, we cool.”

I saw him for the next two years of my life at that cafe and we became friends. In fact, he hired me to work for him (kinda) about six month later. I introduced him to some people I knew and he did the same. Eventually, we had a cafe crew. His name is Parker. Thanks Parker.

Meeting People in a New City is Science.

Don’t “make friends.”

Planting seeds is better than “making friends.” Every time I say “hi,” I plant a seed. The more “hi’s” I say on any given day, the more “hello’s” I’m likely to get back. Once a “hi” has been exchanged, it’s much more likely the “hi” will escalate the next time I see that person. But don’t try and go on a hike together right away. I don’t want to go for the gut on the first encounter; that’s just weird. Slowly becoming seen and being friendly is a better way to ease into a new pool of people. 

There was this other time at that same cafe that I met Parker at when I asked this other dude with a mohawk what he was working on. 

“Ehm werkhin on eh ducuumentrary about my cuntery Côte d’Ivoire.” 


“You know Ivory Coast?” 

I didn’t know that shit but I looked it up. Anyway that’s not the point. Point is he told me it was all about how soccer united his country. He said he was in LA trying to raise money for this movie and told me about how, little by little, he was getting people involved.

He and I kept in touch for the entire six years I lived there and I was able to see him go from a dude with a mohawk in the corner of a cafe trying to raise money for his documentary, to a filmmaker that raised the capital, and shot, directed, and produced his first movie.

I really liked that dude.

Anyway, I wrote this article for Playboy a while back. It was one of my biggest accomplishments as a writer. The article was all about how to have sex while traveling the world solo, but I was thinkin about it while writing this blog post and I think how to meet people in a new city is pretty much the same process. It’s all about location. You’ll always meet people in a new city if you position yourself properly.

If you’re traveling, or even if you’re not traveling, consider a walking tour. I know… Sounds odd, but hear me out. Walking tours are great for meeting people in a new city. There are tons of tours you can go on when you get to your destination, whether it’s travel or permanent, and nearly any tour will provide ample opportunity to get to know–not only the city–but the people on the tour with you, but… the best tour you can possibly go on is a walking tour. 

Walking tours are great to start meeting people in a new city. 

I guess this is more for traveling, but it’s great for getting to know your new hometown as well. But DEFINITELY if you want to meet people and travel, this is key. Basically, a walking tour is a free tour where a few locals will walk you all around different neighborhoods and show you what you may not see on your own. You’re walkin around with other travelers for hours and there’s plenty of time to talk and make friends, but just know it won’t happen randomly all the time. You still need to put yourself out there a bit and ask people where they’re from and why they’re there and what the shittiest place they’ve been to so far is; you know, converse. Otherwise, you’ll be walking alone. Point is it all starts with positioning yourself properly and walking tours are a great option.

But sometimes, shit goes wrong…

I once went on a walking tour in Medellin, Colombia called “real city tours” and it was pretty scary actually. The whole point of the tour was to show you the “real Medellin,” you know, the Pablo Escobar Medellin, the one you secretly wanna see but are too scared to ask: “hey where’re all the coke kingpins?” Well that’s what this tour was all about. Anyway, we were downtown in the city center and the tour guide was all like:

“See? This is where they say you should never go; that it’s too dangerous. And look, here we are. Not as bad as they want you to think right?”

And just then some random dude from the street walks up to the guy next to me and tries to sell him some silly shit that no one would wanna actually buy. The tour guide was all like:

“Yo, do you mind?”

And from 0 to 100 this guy erupts into fury sayin shit like:

“You’re allowed to try and make money but I’m not?!”

Then the guy starts screaming at the dude next to me asking for a sip of his water. lol. Oh man it was scary. So glad he’s not talking to me… He kept saying “LEMME FIX MYSELF WITH SOME OF YOUR WATER!”

He said it in Spanish so maybe it translates differently but finally the guy next to me gave the rando his water and the rando refused it and walked away. The tour guide was this kid in his early twenties. He looked so jacked up on nerves, like he was gonna pass out.

“Sorry about that guys… but you know, this is the real Medellin, right?” 

But he was scared. You could see it in his face. He hustled us the fuck outa there and off we went. But anyway, it was a great place to meet other people.

Now I wanna talk about hostels, and hostels aren’t just for travel…

Meeting People at Hostels

girl waving hello

When you travel, staying at a hostel is a given. If you’ve never stayed at a hostel, the whole point is a community lodging experience. You can stay in rooms with ten people or private rooms by yourself. Regardless of where you sleep, you can mingle at breakfast or throughout the day with millions of people. Nearly every wonderful experience I’ve ever had, whether it be road tripping through Peru or Spain or watching live music in Nashville or chit chatting in Fairbanks, all of these moments were born at a hostel. I could just say that if you wanna know how to meet people in a new city you just go to a hostel and you’re going to meet a hundred people whether you like it or not, but that’d make this a really short read. But if you’re into short reads: the way to meet new people in a city is by staying at a hostel. And not just if you’re traveling… 

Before I moved to LA I stayed at a hostel in Hollywood, and then another hostel in Santa Monica just to see how it all was. In fact, I stayed at a hostel in San Diego before that just to scope that city out too. Even after I moved to Hollywood I STILL stayed at the hostel every now and again to meet new people. A lotta people do that shit. In San Diego there was a guy who just moved there and was working and looking around town for an apartment to live in. When he found one he moved from the hostel to his apartment, but by then he had already been exploring the city so he knew where to go.

In Buenos Aires I met a brother and sister from Venezuela that were also looking for work and an apartment. They met a buncha people just off the recommendations of where to go from the hostel staff, and before I left for Patagonia, the sister had a job at a restaurant and they found an apartment not too far away. So, hostels are great no matter why you’re in a new city, and age means nothing. Most people are young, but many people are in their thirties, forties, fifties, and sixties.

Like this one guy I met in Alaska that changed my life. He was like sixty or something before he died. It’s a bit of a long tale, but the gist of it is I was searching for meaning in life and told this stranger all about my woes. He listened carefully and gave me some feedback that never left my head. He was dying of cancer and told me things nobody had ever told me. His name was Alex, and you can read about our story here.

How to Meet People in a New City – Don’t Fear Rejection

Some people don’t wanna make friends, so don’t get all bitter when they say “nah” when you ask if they wanna do something together. Sometimes people don’t want any more friends, but that doesn’t stop me from walking around main street and going into every store and telling the shop owner I just moved to town. Usually people like to meet the new people who just moved to town anyway. And if you’re in a big city, the more people you tell you’re a newbie to, the more other newbies you’ll meet. So many people are waiting for someone (anyone) to just say hi. It’s all about saying hi. If conversation is the way to meet people and “hi” is the start of every conversation, it only makes sense to start there and do it a bunch.

Like this one time I said “hi” to this Canadian chick in the hostel bed across from me. It was actually at the same hostel I met the Venezuelen brother and sister at. Anyway, the Canuck was a nurse and had just lost her job and as it turned out, she had never traveled before or traveled alone at least and she was freaking out. I was able to help her plan her agenda to do iowaska in Peru (which she never ended up doing) and then we traveled all over South America together, leaving each other in certain cities and meeting back up in the next to exchange travel tales with each other. At the end of our trip it felt like we were best friends. Especially when we crossed the border by land from Ecuador to Colombia and she was declined at customs.

Here’s what happened…

We had to sneak her across the border for the night because my passport had been stamped and hers hadn’t been, but we were traveling together so we had to stick close. Plus, it’s a bit shady around that area of the world… Anyway, she still had to go back to Ecuador the next day to get her passport stamped so we stayed at a crumby hospedeja and then she went back across the border the next morning to get the cash she needed to get her passport stamped and then she came back to Colombia and met me at the hospedeja and we traveled to Cali (Colombia). I still talk with her. She’s back in Vancouver.

Building Relationships Takes Time and Work.

Don’t make soft moves. When you’re making conversation with some people at a bus stop, don’t let it die out there. Take it to the next level if you’ve got the huevos. I was listening to Caitlyn Jenner on The Cabin (that comedy TV show with Bert Kreischer) and she was a guest on the show and was like: 

“I didn’t run 72 miles a week to run the last 400 meters slow (cause she was an Olympic runner when younger).” 

Anyway, she said something like that and it stuck with me. That’s how I feel about this. You don’t put yourself out there, find yourself in a good conversation at the bus stop, then leave without exploring more of the relationship.

Like this one time in Argentina when I was waiting for the bus back to Mendoza and found myself talkin to a buncha French people. It was their last night in South America and I told them I wanted to help them celebrate their last night. So I met up with them later that night. I just gave the girl I was talking to my phone and she put her number in and we met later that night and kept in touch for about a year afterwards. There’s actually way more to this story but you can read about that in another post. Here’s that story you can save for later…

Make Plans with People at Breakfast

When you’re traveling, nobody has any idea what they’re gonna do for the day, so the best time to make plans with the people you’ve met at a hostel is at breakfast. Catch people before they leave and make sure you have a few suggestions ready for what you can do together. Be prepared. 

“Wanna go paragliding today?” 

Whatever it is, ask in the morning. Everyone wants to make friends while traveling, so it’s not weird one bit to ask to join forces and explore the world together. 

I was sending out press releases early in the morning in Santiago Chile once for a PR client I had from my laptop in the common area and some chick from Argentina was having coffee next to me. She got up to leave and before she left, I asked where she was going for the day. She had no idea. She said she found some cool pool in a park she wanted to check out. I asked if I could come. Then we went to a pool I never woulda encountered on my own.

The moral of the story is the secret to meeting people in a new city is to have a system, be patient, and position yourself correctly. 

Now here’s a story that answers the question: WTF is vagabonding?

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