The Girl with the Brown Wool Cap

March 07 2012 2:40PM

I walk around on a nice spring afternoon.

I notice a girl sitting near the overpass with her intriguing brown wool cap.

“Hey, that cap looks really interesting. It would be cool to talk to you.”

She smiles and says yeah sure.

We end up talking about that brown cap for a couple of minutes. I recall her stating that it was made from an old dress. Her friend recycled a brown dress and ended up knitting it into a brown wool cap.

She tells me she was 24 and a fifth year super senior. She also states that she took a year off to try culinary school in New York City where she ended up living in a closet.

Her blue eyes light up at the mention of having to reside in a small closet. She seemed really proud of this particular fact about her life. She told me it was an amazing experience and she would’ve done it again. She definitely was the adventurous type.

However, she decided to go back to campus to study film. She wanted to do a documentary on GMOs in our food supply. I tell her that it’s an important issue regardless of where one stands with it. The majority of some of our crops are genetically modified so it would be great to see a documentary on it.

We talked about that for a couple of minutes.

Then I told her I had to get going and wanted to chat with her again. I asked for her number.

She gave it and we both smiled. Then I went on my way.

The lesson of the post is: tell your story as well. During the 15 minutes, I rarely talked about myself. I didn’t allow myself to be vulnerable which made her lack incentive to contact me in the future. She never answered the couple of times I tried to contact her. Make yourself interesting enough to be attractive.

The Social Skydiving Game: Flirting with 77 Women in 14 Days

Let’s define social skydiving. Social skydiving is the art of chatting and meeting strangers randomly in order to make a new friend, get a date, get over social anxiety, or any other form of getting out of your social comfort zone.

Why would anyone want to do this?

Being shy for many years of my life cost me many opportunities to interact socially. After all those years, I wanted to do a social experiment that allowed me to have something anyone would want: Choice.

When it comes to meeting people through your social circle or a particular group (especially in college), the people are prone to be similar types of people. For example, imagine joining a Psychology club where all of the people in the group at Psychology majors.

Nothing is wrong with that but I wanted variety and choice. I also wanted a challenge to allow me to take risks. This ended up fitting both of those needs.

One of the most important learning lessons

You’re going to mess up and that’s okay. This was the first time that I approached strangers with the intent of flirting with attractive women.

Some approaches had women look at me strange. Others smiled when I started talking. A few of them were stunned by my confidence. A couple of them were mocking me by my awkwardness. The ups and downs of these approaches allowed me to take positive reactions in stride and the negative reactions without offense. It taught me to focus on a stable, content mood throughout the experience.

The actual experiences

I spend a few hours walking around chatting with women. Just like anything else, it takes practice to improve your social skills and flirting skills. Many of them lasted less than a minute. Others had a duration of over an hour. I met a wide variety of women studying many different things. I met girls in their 1st year and girls in their 5th year. I met some of them waiting around for a few minutes for the next class and others walking into town.

Social skydiving doesn’t have to take that many hours of your day but it allows random encounters with people you wouldn’t have met otherwise. Even if you took 10 minutes to chat to someone you found attractive or interesting, it could end up making a major difference. I consider it a valuable skill that pushes you out of your comfort zone.

What about creepiness?

The topic of creepiness would come up sooner or later. I have utmost empathy for people. I always made sure that the girl I approached had personal comfort and safety with the interaction. If she was getting fearful or she seemed like the type that didn’t like what I was doing, I would tell her it was nice meeting her and be on my way. If there was a major lull in the conversation, I would tell them that silence can be golden because both people are trying to figure out what to talk about. If we didn’t have much in common I would tell them it was nice meeting them and move on.

I opened up and told some of them that I had social anxiety and I wanted to talk to strangers to improve my social skills. They smiled and accepted to talk to me for 5-10 minutes. There was also a few approaches where I didn’t state my purpose and it made it weird in the long run. I learned to state your intent. It doesn’t always have to be right away. I learned to state it eventually or risk hovering around without a purpose.

Honest transparency delivered in a clear, confident tone eases the other person to start a conversation as well.

Redefine your definition of success

My definition of success during these approaches was to actually do them. No matter how difficult the task seemed, I got joy out of just partaking in the task, regardless of result. It was my personal zen-like activity to calm me down. Success was knowing that I passed through my own personal fear each and every time I went up to an attractive stranger. Then I noticed that many of my regrets disappeared as well when I took a chance to chat with somebody I wanted to.

The calm wave upon me had arrived.

For the next couple of months, I’ll write about some of the more memorable approaches during this time and what you can learn from my experiences. If you liked this post, please subscribe to get quick updates.

[In ode to Niall, who wrote an fantastic post on flirting with women. Much of my inspiration to do this came from this post. He also helped me stay accountable for my efforts through e-mails. I participated in this for 14 days from March 1-March 15 2012.]

The Revival

After the past calmed me and put in a meditative-like state, I decided to continue on with my journey.

March 1st 2012

The bright sun on my college campus decided to shine throughout the bike paths and onto the buildings. It was a lovely spring day to stroll around. I was the wallflower, just walking around in the background, adding another layer of static to the scenery.

I noticed all these people around me walking around, doing what they had to do in their day. I thought to myself, “What is holding me back from talking to these people?” I did Rejection Therapy and met strangers from Twitter. I was proud of doing those things. Then it clicked in my mind. I had to combine the two concepts together and meet people walking around me on the spot.

I was going to chat with them.

I decided to go to the cafe to have a cup of coffee. It gave the energy but I was still anxious to partake in my own challenge.

After going to classes, I decided to take one more break. I went off campus and into a small pub, where I had one beer.

All of a suddenly the enlightened clarity hit me. I felt an absolute wave of calm and focus.

This would lead me to chat with strangers all around campus.