This scenario happens all the time: I meet someone interesting at an event and return home to find they’ve already added me on Facebook. I’m nosy, so I want to see what friends we have in common. Turns out, we know 89 of the same people. Which begs the question:

How on earth is it possible to have 89 mutual friends with someone I’ve just met?

I’m grateful to be a part of an inter-connected, pseudo-incestuous group of “influencers.” You’ll find us at South By and Summit. At Sundance and on Path and at the playa. We live in SF and LA and NYC… sometimes all three. We are entrepreneurs and intrapraneurs and actors and musicians and investors. Everyone is a dreamer. Few of us are actually famous.

Introductions beget introductions and before you know it, we’ve built an outrageous crew to roll with us wherever we might want to go.

We organize dinner parties and concerts and raves and adventures and launches and pop-ups and on and on and on. It’s an extraordinary world where we talk about things that matter, build innovative companies and create amazing experiences.

Words like “epic” and “crushing it” are used regularly with the utmost sincerity as if everything in the world can be experienced with flushed face and wide eyes.

I realize how fortunate I am to live this life. There’s a Gatsby-like wonder to the revelry and adventure. My world is dizzying and exhilarating.

But every once in a while, I’m concerned that this always-on way of connecting with people is numbing a reality that should be dealt with:

It’s easy to never be alone and yet very lonely.

Friend vs Friendly

True friends are our best personal brand consultants, the ones that sit us down and tell us the truth about our lives. They understand not just what we do, but who we are becoming. They help expose the lies we tell ourselves and breathe life into moments that need encouragement.They’re not persuaded by high levels of “epicness” or exclusive invites. Friends are content to navigate the mundane and the everyday together, because not everything can be “crushed.”

The world needs more friends. More specifically, the world desperately needs more “connections” to become true friendships.

What I’m suggesting is more difficult than it sounds. And I’m certainly not a living solution to this problem. I have a little trick that keeps a nice barrier up. I ask questions. Lots of them.

“Congrats on the launch! Are you exhausted?

Do you think this new career is going to make you happy?

How are you and your boyfriend doing?”

And so on I’ll go…deeper and deeper until the inevitable question comes in return:

“So wow… I’ve been talking about myself all this time. How are you doing?”

It’s a nice attempt, but I usually opt to dodge the question entirely.

“We should hang out again and I’ll fill you in on me.” Lie.

At one point, I had over nine thousand contacts in my address book. Nine THOUSAND. I wore that number like a badge. I’ve whittled it down now to about a third of that, and I think I could do the same thing again. Who on earth would ever need nine thousand connections to accomplish something? And maybe a more honest question is, “What is it that I’m trying to accomplish in the first place?”

It takes serious time to form a true friendship. It takes great questions with attempts at honest answers. And these answers are hard to discover and convey together as we’re screaming over a DJ set. Or on email. Or even at a dinner party.

All of this is reflected in romantic livelihoods as well. My world is filled with mostly single people. Many newly single. We seem to see a lot of divorce and complicated break-ups. Random hookups. Casual sex. We crave connection, but anything more can seem elusive. There are exceptions, but not many.

Proximity (both physical or virtual) can give the illusion of intimacy. If we’re not careful, we forget what it really means to give and receive true friendship and opt for just being friendly.

Maybe it’s time to be honest with ourselves about the quality of our relationships, to truly identify the real friends in our lives and invest deeply in them. After so many parties, trips, conferences and dinners, maybe it’s time to build a true community, not just a network of endless connections that feeds our collective ego.

If you like this post, instead of just recommending it or leaving a quick comment, consider taking a ‘connection’ to lunch and having a real conversation. Who knows where it might lead.