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

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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, flirt with attractive people, 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. Much of the time, it made them feel really good too because flirting is fun.

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.

How to Stop Taking Rejection Personally

“It’s too bad that I did the bad thing, screw up, but I’m not a worm, I’m not a louse, I give myself what we call USA – unconditional self-acceptance, just because I’m alive and human, for no other reason. So therefore, if you don’t like me, I don’t like that – I’d like you to like me, but if you don’t who really cares? What’s going to happen to me – very little!” – Albert Ellis

Change your idea of what someone is rejecting

Much of the time when someone rejects us, we get frustrated because we feel they’re rejecting our whole being. When they reject your mediocre cooking, they’re rejecting you as a whole. When they reject your favorite music group, they’re rejecting you as a whole.

That isn’t true.

What they’re rejecting is something at face value. They’re rejecting the fact alone.

Change your perspective from they’re rejecting me as a person to rejecting something based on their opinion.

Based on their limited knowledge, they do not like whatever you are presenting and that’s okay.

For example, if you’re introduced to a stranger and both of you have a lot in common, that person doesn’t know that yet. Their first idea may be, “Oh, look at that weird shirt. Yeah this person is too weird.” It’s their bad that they missed out on the opportunity. There could also be a million other reasons that they didn’t like you.

Once you understand that rejection was an old concept to keep humanity together and intact during the days of our ancestors, you’ll understand that it does very little for us during the modern era.

Get past the evolutionary markers and start taking those chances.

Shift your perspective of rejection into feedback that helps you progress to where you want to go

Think objectively about what you could have done better. Remember that for next time.

“Oh I wasn’t consistent with that date because I was too scared to kiss her at the end of the date.”

“I didn’t get a reply because my writing wasn’t organized. I’ll rewrite it and send it again.”

All rejection is feedback to improve on yourself. Think of it as a form of constructive criticism that’ll improve your life.


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On Social Rejection (Albert Ellis’ Amazing Experiment)

“New research suggests that the same areas in the brain that signify physical pain are activated at moments of intense social loss.” – NY Times.

In other words, social rejection.

But social rejection can be beneficial. The pain is telling you to take up other opportunities.

Rejection is the quiet sage that indirectly gives feedback.

So how can someone get over something so painful?

In Vivo Desensitization.

In Vivo Desensitization is using Systematic Desensitization in the real world.

Systematic Desensitization is using small, progressive steps to slowly eliminate or greatly reduce a particular fear. Social rejection is a fear to many people, so this process could help with making friends, getting dates, etc.

For example, if you had a fear of social anxiety, you could create a list of small steps you could do to slowly get over that.

An example of steps would be:

Step 1: Smile at 10 people
Step 2: Look straight in the eye at 10 people
Step 3: Say Hi to 10 people
Step 4: Make a comment to 10 people
Step 5: Talk about one subject to 10 people
Step 6: Have a lengthy conversation to 10 people
Step 7: Have a lengthy conversation with 10 strangers

It may take a lot of hard work but you’ll come out a better person by learning through the grit.

This relates back to approaching. It takes a lot of grit and passion to overcome all of that social pain.

But it’s worth the spontaneity and value-giving.

One of my favorite examples of overcoming social rejection is from Dr. Albert Ellis, one of the most well-known Psychologists.

From this post, At the age of 19, [Dr. Ellis] gave himself a homework assignment when he was off from college. He went to Bronx Botanical Garden every day that month, and whenever he saw a woman sitting alone on a park bench, he would sit next to her, which he wouldn’t dare do before. He gave himself one minute to talk to her, calming his fears by saying silently to himself, “If I die, I die. Screw it, so I die.”

Make a statement that helps you overcome your fear. When it comes to approaching people in general, all it takes is making a personal statement that helps you become at ease, at least enough to execute what you need to do.

Awkward Moments Experiment

“Move out of your comfort zone. You can only grow if you are willing to feel awkward and uncomfortable when you try something new.”
Brian Tracy

I’ve decided to create this to help me take more risks because my final year of college is looming.

I’ll create situations everyday for 30 days where two things happen:
1. I’m feeling extremely awkward.
2. It benefits the other person or group.

I’m tired of avoiding “perceived danger.” I have to let the training wheels go. I’m down to one year, so the pressure is on.

It’s a distant cousin of Rejection Therapy.
The major difference is that I don’t have to ask for anything.

Some examples:
1. Giving hi-fives to random people.
2. Going to a party, even if I don’t talk much. (I tend to avoid them, so that’s awkward.)
3. Wearing my shirt backwards the whole day.

The starting date is:
Sept 19.

Who’s with me?

In the comments below:
-Give me some ideas (reminder: It’s a University Campus)
-Tell me if you want to participate in this too or wish me luck.
-Anything else that’s in your awesome mind.