An Introvert's Guide to Making New Friends and Deepening Relationships


"The most common answer amongst people is that they don't even have one friend that they can turn to in a time of need." - Johann Hari, Lost Connections.

I arrived in New York City like I’m sure many have before me.

A little optimistic, a little scared, and a lot overwhelmed.

But, although this was my biggest rodeo, it was not my first. This was the fourth new city that I have moved to in the last 15 years.

Despite being an introvert, I have become used to meeting new people, making new friends, and building a support network.

But this was New York City. Perhaps it would be harder to do so here?

I heard stories of people who moved to the city in the past and felt terribly lonely, despite being surrounded by 8 million people.

Perhaps I would be next on that list?

It was this challenge that made me clarify my ideas about how to make new friends and deepen relationships.

While I was formulating my ideas, things started getting worse on the national stage.

Armed and Lonely

After yet another mass shooting by someone who was bullied, lonely, and a need of genuine friendship, Bill Maher posted this video.

In his editorial New Rule, Bill addresses America's growing loneliness crisis and its link to mass shootings.

In it, he states that 20% of people in my generation, the millennials, do not have a single friend – 25% don't even have an acquaintance in real life.

This is amongst the most dangerous trends out there right now.

Humans are the ultimate social species.

For millions of years of our evolution, we could not survive the wilderness on our own. Our ancestors who survived were the ones who banded together in tribes.

This is why we evolved to feel loneliness.

Loneliness feels bad because Mother Nature wanted you to be motivated to find a tribe that will help you survive.

Today, we don’t need a tribe in order to fill our basic human needs of nourishment and safety, but the primitive part of our brains doesn’t know that. To our brains, finding a tribe is just as important as food, sleep, and sex.

So if we can’t find a tribe, we begin developing problems.

In his book, Lost Connections, Johann Hari argues that almost all of our problems stem from not having great relationships with others.

He points out that not only can you see this problem amongst the mass shooters out there, but also amongst the drug addicts, homeless, anxious, and depressed.

With all of the negative consequences that occur when you don't make friends, why don't we have a methodology for making new friendships?

Why do we leave people to just figure it out for themselves?

Why do we spend so much time talking about the problem of loneliness without offering a clear solution?

With the consequences of our lonely society growing, I set out to find that solution.

As an introvert, making new friends and deepening relationships has never come natural to me. I have never been able to rest on my natural talent to find new friends. I have needed a strategy.

What I learned so far will hopefully guide both introverts and extroverts alike toward more deep and meaningful friendships.


The first thing to note is that social media is not required – and probably makes things worse. I left social media two years ago and my friendships have not only deepened, but they have grown.

I am now friends with many more people than I ever was on social media.

Of course I don't have the literal quantity of “friends” now that Facebook said I did. But when it comes to genuine, deep, human friendships, I have many many more.

Because although social media allows you to connect with one another, it does not allow you to bond.

You may be able to comment, like, and share status updates with one another on social media, but you cannot deeply confide in anyone.

You cannot share your problems in a honest and meaningful way.

You cannot provide advice and support in the way that we have evolved to do.

Social media is a performance. Even if you are vulnerable and ask for help on social media, people will only respond with the advice that sounds good — not the advice that you really need.

You need those face-to-face interactions where you go through hard times with people and come out the other side stronger as individuals and with a stronger bond as friends.

Social media may increase the number of people that you know, but it cannot deepen the bonds that you have with them.

Especially because it provides a platform for your ego to flourish. And letting go of your ego is the first step to building deep and meaningful friendships.

Step 1: Let Go of Ego

Ego focuses your attention inward.

It is the thing that makes you feel good about getting the validation of likes.

It is the thing that makes you feel miserable when your post goes ignored.

It is the thing that makes you feel “special” and superior when you succeed.

It is the thing that makes you feel lonely and worthless when you fail.

Ego, more than anything else, will be the thing that prevents you from forming deep and genuine friendships.

A friend is someone who genuinely wants the best for you. In order for that happen, the other person has to put their ego aside and put your interests ahead of their own.

The same applies for you. If you want to develop real friendships, you have to put your own ego aside and focus on being the best friend you can be for the other person.

Thus, the main change in mindset that you must have if you are to make new friends is to focus on them and not yourself.

Don’t think about making friendships for your own personal gain.

Think about the fact that other people are probably just as lonely as you are. They need a friend just as much as you do.

If you can let go of your own ego and focus on simply being the best possible friend you can be for someone else, they will return that friendship to you.

This may seem unfair…If other people want new friends, why aren't they setting aside their own egos to be the best friend they possibly can be for you?

If that thought crossed your mind, you now know what your ego sounds like. Do not listen to it.

If at any point during the rest of this article that little voice inside your head says “things aren't fair” or that “other people should put in this work and I shouldn't,” that is your cue to stop listening to that voice.

That voice is the key thing that is going to get in the way of the true happiness that you can develop through rich human relationships.

Everything that I recommend from here on requires that you set aside your ego and put other people first.

Because that is what genuine human relationships are built on. People being there for other people.

Step 2: PlaY OFFENSE

Now that you have let go of your ego, the next step is to understand that you can't just wait around for friends to come to you (playing defense).

You have to play offense.

The vast majority of people are not going to come to you looking to make plans. This is not necessarily because they don’t want to hang out with you.

Lots of people are busy.

Lots of people are also shy and introverted.

Lots of people are hoping that someone else makes plans and invites them to come.

When I first moved to New York, I only had three loose connections in the city.

Even though these people all knew that I was moving to New York in May, I couldn’t just wait around and expect them to reach out to me — I needed to reach out to them.

I wasn’t sure exactly what each of them would be interested in doing, which could have led to analysis paralysis. I could have worried incessantly about whether or not what I proposed would be “cool enough” for them.

But that would’ve got me nowhere. Instead, I reached out to each of them just to get a cup of coffee.

Only one of them actually accepted my coffee proposal. One of the other two suggested we explore Prospect Park in Brooklyn. The other one suggested we get brunch.

Perhaps I could have come off “cooler“ if I had looked up their social media‘s and seen what the other two were interested in. But that wasn’t necessary. All that was necessary was trying to set up a situation to hang out and get to know one another better.

Most people are genuinely grateful when someone else plays offense and invites them to something fun — especially if you follow the next step.

Step 3: Seek to Understand

Once you are able to set up a meeting with someone else, the biggest mistake that people make is worrying incessantly about looking cool.

This is the egotistical angle.

Your ego isn't just arrogant. It's also fragile.

If you are worrying about whether or not you’re “good enough,“ “cool enough,” or too socially awkward to hang out with the person that you’re meeting, your attention is focused on the wrong thing — yourself.

You must think about them.

Everyone has a desire to be understood. This goes beyond the narcissistic need for someone to talk about themselves. We all want someone to take the time to truly get to know us.

If you can give that gift to another person, they will give it back to you in return.

After setting up my plans with each of my loose connections in New York, I went into each interaction not trying to put on a performance that I thought each person would like.

My attention wasn't focused on me. It was focused on them. I genuinely wanted to get to know them better. I wanted to learn about their experiences in New York. I wanted to learn what advice they had for someone like me who just arrived.

Each of them had knowledge and experience in my shoes. So each of them was willing and eager to share their advice with me.

The most important thing in this step is genuine curiosity. If you are as introverted as me, you will not find it natural to meet with strangers or even loose connections. You will worry about what they think about you.

But, introverts have an advantage when it comes to building genuine friendships – asking questions.

Extroverts relate to one another by sharing stories. Introverts relate to one another by asking questions.

If the person you’re meeting with is an extrovert, then they will be deeply grateful you’re asking good questions and genuinely interested in what they have to say. Rather than just waiting for your turn to speak.

If the person you are meeting with is introverted, then it will be a little bit more difficult to get them to open up. But, once again, they will find it refreshing that they are meeting with someone who can ask great questions and is genuinely interested in the answers.

This step is where ego can really get in the way.

The other person may not be as comfortable seeking to understand you as you are seeking to understand them at first. Give them time.

In our self-obsessed culture, people may not be used to someone who is genuinely curious and empathetic. They may not even know how to express these qualities themselves. Don’t hold that against them.

Instead, as your friendship grows, let them know of your genuine desire to understand who they are as a person.

In my own friendships, I have been upfront about my introverted nature and how resting on my natural curiosity is what allows me to build friendships with people like them. They are always fascinated to learn more. I’m sure they will be with you as well.

Especially if you succeed in Step 4…

Step 4: Show AppreciatIon

With a good understanding of your new friend — and a focus on them and not you — you can start to find things that you genuinely appreciate about them.

Like with being understood, every single person wants to be appreciated for the things that make him or her special.

If you can give the gift of genuine appreciation to another person, they will be eternally grateful.

Appreciation is different than flattery. Flattery is generic. It looks at the surface level elements of a person and tells them what you think they want to hear.

If you took the time to genuinely understand the person you are meeting with, then you will notice things at a much deeper level that you appreciate about them.

They may be talents that you don’t have yourself, they may be characteristics that you respect, or admiration for adversity they have overcome in life.

As you are asking questions, open your mind up to the things that you genuinely appreciate about this person.

Everyone of the three people that I met with had something that I genuinely appreciated about them. For each person, it was different.

For one, it was the fact that she left Nebraska to move to New York to pursue her dream in the fashion industry.

For another, it was the fact that he was a far more successful entrepreneur than I was.

For the third, it was the fact that, as an extrovert, he had the confidence to make friends with random strangers that I don’t have.

I genuinely admire each of these traits in the people that I met with. And by communicating that appreciation effectively, it made the other piece person grateful and strengthened the bond between us.


The last step in creating genuine human friendships is to be vulnerable.

Now that you have started building a genuine bond with this other person, it is time to open yourself up to be vulnerable.

This is not easy – especially for introverts – but this is what will take your relationship from an acquaintance to a genuine friendship.

If you've done your job well up to this point, the other person is eager to learn more about you.

This is where people can start making mistakes. Insecurities make us believe that we should only share our positive qualities.

This may get you more likes on social media, but it will not help you build a stronger bond of friendship.

However, being vulnerable is far from easy. I have found the best way to share my vulnerabilities is to connect them to things I genuinely appreciate about the other person.

For example, my new friend who moved to New York to pursue her dream in fashion, I shared that I would never have had the confidence to move to New York as a 22-year-old as she did. I barely summoned the courage to do so as a 29-year-old!

For my entrepreneurial friend, I shared some of the key mistakes that I have made so far in my entrepreneurial career and asked for his advice.

For my extroverted friend, I shared how it was hard for me to meet new people so I’m deeply grateful for people like him who make it easy.

Admitting each of these things to people I met with was uncomfortable. But to them it was endearing.

Say instead that I had let my insecurities get the best of me with my entrepreneurial friend. I would have told him all of the successes that I've had as an entrepreneur, hoping that would make him like and respect me more.

But that would have undoubtedly led to him talking more about his successes and kept everything service-level.

Instead, he shared some of the mistakes he's made over the years and what he learned from those experiences.

Those are the deeper conversations that lead to genuine friendships.

It's easy to share your successes with somebody. That's why we find it so easy to share our wins on social media.

If your goal is to simply add more friends on Facebook, share your hopes, dreams, and successes.

If you want to gain real friends, share your fears, insecurities, and failures.

How other people respond to that will show you who your real friends are.


In 2015, after raising $13,000 on Kickstarter to write The Will of Heroes, I moved from Chicago to Florida to seek solitude and write the book.

I finished the book in six months, I stayed in solitude for three years.

I thought that I was doing the smart thing. I was still trying to succeed as an entrepreneur and I was devoting myself entirely to my work.

But, despite the fact that those three years were the most productive of my life, I didn’t accomplish much of anything..

Even though I was making a living in a tropical paradise and working on things I was passionate about, I was missing something vital to the human experience—friendships.

I was lonely.

That loneliness motivated me to visit a friend of mine in New York. During my trip, he introduced to his friends and I decided to move to the city.

Going from solitude to one of the largest, most intimidating cities in the world, was not easy. That’s why I came up with these steps to help me make new friends and deepen relationships.

They have taken me from three loose connections to dozens of great friends in less than six months.

If you can set aside your ego and follow the steps above, I am confident you will achieve similar results.

And as your friend group grows, so will the amount of understanding, appreciation, and vulnerability in our world.

That is something we could all use more of.