Get out of jail










As the weeks passed, my coach and I decided it was time for me to spread a message. It became a way to have a little more fun when I stood on the street corners, waiting for someone to compliment. We came up with the idea of handing out cards. These cards, made crudely in Microsoft Paint, contained the message “You’re Already Free,” along with the Monopoly Man flying out of his cage. I printed them out, and took them with me to the streets of Berkeley.

There I was, standing awkwardly in the cold, waiting for unexpecting pedestrians to walk by and take my card. Most people took the card and kept moving, without looking back. Did it mean anything to them? I’ll probably never know. Some would give me a dirty look, or laugh at the piece of paper they just received.

One guy had been standing nearby, waiting for his group of friends. At first he didn’t seem to mind me at all. Eventually he came so close to me that it was almost impossible for me to avoid him.

“Would you uh… like a card?” I asked him.

“What are you doing out here?” He seemed skeptical, but interested.

“Nothing, just handing out cards.”

“Alright, I respect that… What are you selling?” He knew I was up to something, and was trying to figure me out.

“I’m not selling anything…” Taking my card and looking at it, he asked:

“You’re already free, huh? What does that mean?” I could see how he might read this as an empty, banal message.

“It means exactly what it says! It means you’re already free to speak your mind, to do what you want in the world…”

I was trying my hardest to convince him, to sell him on the idea.

Maybe I was selling after all.

He started asking questions about me: where I’m from, whether or not I was a student there. We didn’t have a whole lot in common. He was trying to categorize me in some way, but probably couldn’t come up with the right label. I ended up doing the same thing when I asked:

“Are you a student here?”

“Yeah, Berkeley Law.”

“Do you enjoy it?”

“It’s alright… It’s something good to work towards, you know?” He said with some resentment.

To some extent I felt he was looking for freedom on the other side of some destination: after his finals were over, after his graduation, after he secured his first job as an attorney. That could, however, just be my projection. Still, I wanted to ask him: “Do you feel like you’re already free?”

But I didn’t.

Before I knew it, his friends came by. We shook hands and he walked away. I stood there, wondering if my card had any impact on him. That little piece of paper, containing the message that I stand for.

The next day, returning to my coach, I recognized the gap between what I believe, and what I actually do.

“You believe you’re already free. Well now, you’re going to step that up. This week, forget the script. Just say: ‘Hey, you’re gorgeous. Do you want to get a coffee with me?'”

My stomach turned. I figured there must have been a few steps missing. I didn’t think I was ready to be that direct. Remembering the gap in my integrity, I reluctantly accepted the assignment. For the first time, I’d be leaving the house for the sole purpose of hunting women. I was doing exactly what I’ve judged so many guys for doing. Eventually it hit me: how we shame each other for going after what we clearly want, and that I was just as guilty of a participant as anyone.

The first girl I invited to coffee was sitting on a bench at a shopping mall. She was looking down at her phone.

Whatever, Rolando. Just get this over with,” I thought to myself.

I made my way over to her and said exactly what I had planned:

“Hey you’re cute, do you want to get a coffee with me?”

Without a pause, she replied: “No, I’m actually waiting for my boyfriend right now. Sorry.”

To be honest, I forget what the hell I said afterwards. I heard the words “Waiting for boyfriend” and decided to scram before he got there.

Was I unwanted attention? Absolutely.
Was I being creepy? Well, maybe.
But did I show up? Yeah, at least once.

And for just a few more times after that. A few days ago, upon visting my coach in San Francisco we decided to go for a walk. After spontaneously choosing a direction to walk in, we arrived at a cafe. He knew I’ve been letting myself off the hook, that my resistance to change was getting the best of me. Once we got seated, he asked if there was anyone in there I liked. There was.

After a little convincing and planning, I walk over to her table and asked:
“Hey do you mind if I sit down to talk for a few minutes. Just wanted to ask about that book you’re reading.” She agreed, and I took my seat. Realizing that I wasn’t really honest about my intentions, I said: “I think you’re gorgeous, that’s really why I came over.”
She smiled and we continued talking about books, school, and whatever came to mind. That wasn’t so bad after all. Eventually, she says she has to go: her family was getting together, and they were waiting for her.

And that was that. At the time I didn’t particularly feel like getting her phone number or anything. I was still pretty surprised at what just happened.

All that takes me up to where I am now. I wish I could say that I’m uninhibited, and that I swing at every pitch. I think a lot of guys would like that. Whether I’m talking to the law student on the street or the girl at the cafe, just speaking my mind has always been one of my biggest challenges in life. I have yet to receive a really negative response from anyone I’ve interacted with these past several weeks, and I dread that that will change. But I do realize that in order to do what I want in the world, I’ll have to accept being judged and criticized for it. What I actually want is to step into my light, and bring my message out into the world:

You’re already free: from your childhood conditioning, the rules of engagement, and social expectations.

Thanks for reading,