The Paradox of Reaching Out (Or Let Them Prefer Solitaire)

“You can’t stay in your corner of the forest waiting for others to come to you. You have to go to them sometimes.” – A.A. Milne

Let’s go with the forest metaphor. When you’re attempting to reach out to someone without any previous knowledge or any idea what their likes or dislikes are, you’re going into a new territory of the forest.

You need a certain type of bravery to continue on the path, even when you have relatively few clues (clothing, other external items, environment) as to how someone will react when you attempt to go to them and actually try to interact.

Here’s my personal example:

September 1st, 2011. 10:37AM in the train tunnel that connects Oakland to San Francisco.

A woman that sat next to me was playing solitaire on her phone. I had no idea what her age was and no idea what her plans were.

I decided to write on my iPhone, “Let’s talk instead of having you play a boring game of solitaire.” She had earphones on, so I figured this was a compromise between my fear of actually doing it and having her to actually take the damn things off.

I tapped her on the shoulder and made her read the message.

Here’s the awkward part: She didn’t understand what was going on.

At this point, she took her earphone off and looked dazed and confused.

Then I had to explain to her that it was a light joke and I wanted to talk to her about anything really.

I ended up half-joking that, “Well I saw that you were playing solitaire there so maybe we could have a conversation that’s more interesting than that.”

She said, “Sorry.” and turned away. Then she continued playing solitaire.

I thought the iPhone message was funny and creative. It turns out I was wrong but I would’ve never known until I tried.

I was satisfied that I tried.

The paradox of reaching out to people is that only those who are open enough to receive it will be willing to talk to you.

Some people are too shy themselves, others get nervous if you’re not perfect (and show nerves to actually try), even more think you’re a flat out creeper, and the rest don’t connect with that certain depth. Also, there’s probably a million other reasons.

Okay. So?

I’m welcoming them and giving them the chance to interact.

The rest is out of my control and outside the circle of influence.

Chris Barba
Chris Barba

Ha - Love it Matt! Man you're really breaking down those social barriers. Seriously inspiring dude. And I love your outlook on these things. Even if they don't work, it doesn't mean you should stop taking social risks - in fact that is the point of social risks that they don't all work out. And what you have to show for greater sense of you, an evolving character, and an inspiring story. Keep em coming Matt!

Hugo Martins
Hugo Martins

The idea of writing on your Iphone was really really cool. I'll try it one day, for sure!


This is really interesting. I talk to random people at times. Or random people will talk to me. Sometimes I'm made nervous by the type of person who wants to speak with me - like I have more ease around women than I do with men. But I think this idea of being in our own world is really intense. Loads of people - myself included - walk around with our ipods (or walkmen!) blaring, chatting on the phone or just trying to rush from point a to point b. Generally though, I think that people's personal space and time should be respected and people shouldn't be looked down upon if they're not interested in speaking with you. Because sometimes I don't want to talk to people and be in my own space in public. It's a fine line!


Matt - awesome - the awkward experiment has already started - lol - i don't know if this counts or not! It's great you did this and you took a huge risk and did all that but it's If you don't consider it awkward, can't wait for your 30 days of awkwardness bro. And no - awkward's not bad - sometimes the more awkward things we do, the more success come our way.