Directness (Or Finding Magical Connection)

Back in March 2012, I flirted with many girls to systematically desensitize my fear of talking and flirting with strangers I’m attracted to.

I reflected upon what I needed to improve.

The problem in those interactions was that I had a mental block. I didn’t allow myself to directly offer whatever I wanted. I would use context and converse with people extremely well but I would never state my intentions.

I never directly told them what I wanted, whether it was to be friends with them or date them. I never told them how long I’d stay around in the conversation and was unsure where I wanted to bring the successful interactions. This left a degree of ambiguity in the interactions.

Have you ever had that feeling of ambiguity in a certain situation? You feel as if the person is present with you and the conversation is going well but there is this nagging feeling that they are hiding something from you.

I knew that learning directness was the next step in my progress to become a risk-taker and somebody who could go into the uncharted lands outside of the comfort zone.

The first direct attempt

April 2nd 2012 3:00PM

I’ve been walking around nervously for half an hour trying to be brave enough to chat with a girl in a way that directly states my intention.

All of a sudden in front of me, a beautiful girl walked to her bike undoing her bike lock. I initially walked by her because I was too afraid.

Fear does not ever take a rest.

I took a deep breath and turned around and spoke up.

I said nervously, “Hi, you’re easily the prettiest girl I’ve seen all day. I’d like to talk to you for a few minutes.”

Mind you, I was incredibly nervous at this point, I could barely burt it out.

The girl blushed uncontrollably and smiled at me, “Wow thank you. I’m Claire, what’s your name?”

“I’m Matt”

“Anyways Matt, I have to get going and I have a boyfriend but thank you for making my day.”

I smiled back and went on my way.

Throughout that day, I had a few other attempts that were miserable, terrible, and downright awkward piles of hilarity.

I had a blonde girl look at me like I was a waste of existence through my nervousness and told me “Look I’m going to class, I have a boyfriend from LA, please go.” Another girl looked at me like I was messing around with her and she couldn’t believe what I was saying.

I also had a polite conversation with another girl for a few minutes before she told me, “I’m sorry. I don’t hand out my phone number to strangers outside of my dorm.”

It shocked me but some people need that systematic way to meet people, that’s fine for those who need it. We’re incompatible.

No problem.


The magical direct attempt

This would lead me to one of the most successful interactions I’ve ever had with a person to this date. This person made me learn a lot about myself and what I had to offer the world. She changed my idea of what it meant to approach the people that move you.

April 5th 2012 4:31PM

At this point I was feeling a little discouraged. I didn’t mind the rejection but I felt as though I wasn’t delivering my directness correctly.

I was walking towards the bus station to go back to my apartment when suddenly a stunning girl registered in the corner of my eye.

This was different. This was definitely different. I truly felt there was a magical vibe when she walked by for that split second. The feeling of wonderment and awe shook my soul into action. I had to talk to her and at least give myself a chance. I briskly walked towards the cafeteria to locate her. Luckily, she stopped at the cookie section in order to order a cookie.

I made eye contact with her and it was incredibly powerful. I could feel her welcoming gaze. I said to her absolutely confidently, “I saw you walk by and I found you way too interesting, so I had to come chat for a minute.” She smiled so wide and laughed with joy for many seconds. She couldn’t believe what just happened but I could sense her spirit woke up from the dreaded routine that washer day.

I asked her what she was listening to and she told me Flying Lotus. She took off one of her earphones and made me listen to it for a whole minute. She told me right off the bat she was allergic to peanuts so she obviously couldn’t get a cookie with that. I laughed and told her, “So you told me something right away that I could use against you?” We both laughed quite hard for a while.

That’s when I knew I finally found somebody I could really click with.

She ended up buying a snickerdoodle and halving it with me.

We walked toward her class that was about to start at 5PM while chatting about metaphysical ideas about the world like being able to give clean water to the rest of the world or being able to share mircochange into the world to make a difference. We both smiled, laughed, and had a magical connection.

After about five more minutes she had to get to class, so she put her number in my phone and told me we’d hang soon.

We did but we’ll get to that soon.

All this happened because I took the time and had the courage to say “I found you interesting.”

Why does directness work?

It forces the other person to polarize as a reaction. It increases their chance to be direct back towards you. There is no ambiguity because everything is truthful and upfront.

While it increases the chance for people to say no for any number of reasons, some in my control [like how I deliver myself and present myself], and others out of my control [boyfriend, not into my look, race, too short, bad mood], it enhances the intensity of interactions that are successful.

It makes them more magical.


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

Image Source

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.]

How to Become Comfortable with Awkward

There are countless times when I’ve seen or heard someone says, “Well that’s awkward.”

It’s one of the most unfortunate things of this generation.

When people reinforce that doing something out of the ordinary is awkward, the subjective emotion towards that particular action is negative. When you continually pound it into people’s brains that doing certain things is awkward or wrong, then they will be less likely to do it.

People learn from making mistakes. If you’re less likely to do something because it’s awkward, then you’re subconsciously making it tougher to change: whether that’s your habits, your patterns of thinking, or your social anxiety. It makes it more difficult to accept feeling weird.

So how can you come to peace with the concept of awkwardness?

Let’s define awkward.

I’ll take the 3rd meaning from lacking social graces or manners.

When you lack social manners, people look at you weird. People think that you’re making a big mistake. Even you know what you’re doing is uncomfortable for some reason.

The funny thing is that no matter how careful you are, you will mess up and lack social grace anyways. So why not embrace it?

I came to peace with awkwardness by embracing it. I told myself that no amount of awkwardness would hinder me from learning how to socialize and interact with people. I gave myself the allowance and tolerance to feel comfortably awkward.

Other ways to become comfortable with awkward:

– When you notice you’re in an awkward situation, take a deep breath and frame it as a new experience.
Don’t label uncomfortable situations, let it be.
– Understand that normality will soon arrive.
– Most of the time, it’s only awkward because of society’s perceived idea that it is; don’t mindlessly follow that perceived idea.
– Find comfort in knowing you’re still alive after many awkward situations.

Allowing the silence to pass instead of labeling it awkward

For example, I went up to two girls to chat with them about their choice of Starbucks drinks a few days ago.

I told them, “Hey I really think you’re the two most interesting looking people here. I mean you even have an interesting choice of drinks there.”

At this point, I ran out of things to say. I could feel that this was going to be uncomfortable but I presented an aura of calmness in my lack of certainty. I decided to tell them, “See, awkwardness isn’t so bad when you allow it to happen as it is without judging it as awkward.” They smiled and nodded. I basked in the awkwardness comfortably and told them that it was nice meeting them. I had to get going.

The type of energy you project out towards others will determine how they feel also. When you give off a calm energy, others will be more likely to remain calm as well. I didn’t notice too many nerves because my mind allowed failure and that “lack of social grace”.

Give yourself some slack and find comfort in your awkward actions.

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.

On Belonging (Or the Realization at Starbucks)

“Be daring, be different, be impractical, be anything that will assert integrity of purpose and imaginative vision against the play-it-safers, the creatures of the commonplace, the slaves of the ordinary.” -Sir Cecil Beaton

March 22nd, 2012. Davis, California. 3:15PM.

Maybe I’m fooling myself.

I say to myself, “I’m probably sure that’s another flake” as I sit down on the counter.

I’m seated inside a Starbucks. There’s a line of ten students that crawls through the tables. There’s the counter I’m sitting at. There’s a sofa as well. To my right, around five folks are waiting to receive their drink.

I hear, “Next!”

People are studying for their exams. Some of them are eating food and sipping on their Starbucks drinks. There are around thirty folks in the area. I don’t want to bother any of them.

“Caramel Macchiato!”

I just finished my exams and I was going to meet up with someone. I give her a call. No luck since her phone is dead. “That’s alright.”

Stress is hanging in the air. It feels like thick dread. Everyone wants this week to be over.

“Iced Coffee! Make it two!”

I decide to sit here for half an hour because my bus doesn’t come for another 30 minutes anyways.


Looking straight ahead, a girl is finishing her coffee.

Looking even farther ahead, many of the people in line have their iPhones out. One of the girls has been in line for about 10 minutes now. She’s next.

I wonder what she’ll order.

“Skinny latte!”

I doubt she’ll get that. She doesn’t seem like the type.

Everyone looks dazed or bored. Even the guy at one of the other tables is eating his gyro plate really slowly.

I wonder how everyone’s grades are. Will they get the GPA they want? Will they stress out when they have shortcomings? Will they bask in massive parties either way? What will they do for spring break?


Everyone marches one pace forward. The girl in front walks up.

She ends up getting a Naked juice from the prepared drinks area next to the cashier. I never would have guessed that.

More drinks are called out. I’m still here.

A girl glares at me for a second then attends her textbook again. I wonder if she’s bored out of her mind. That’s too bad. I’m not in the mood to approach. She’s my type but I’m not up for it. Not now.


The line marches another pace forward.

The line never really dies down. Another person or two fill it up once the cashier rings up one or two people. Interesting cycle.

I notice a clique of four people behind the line chatting to one another. I also notice another clique of three next to them.

I think, this is what I’m giving up. I don’t get to have that.

It’s nice for it to be in front of me most of the time I’m on campus. All the cliques and subgroups that people enjoy. The Chinese exchange students, the sorority girls, the hipsters, etc.

All of them can broadly understand one another.

“White Mocha!”

All of the previous times I’ve been here, I’ve heard the same conversation over and over.

“Hey, how is your x class?”
“It’s going okay. You?”
“Yeah it’s cool.”

Sure, the majors are different. The classes are different. The time is different. But is it really that different?

Maybe some majors have to work harder than others but everyone has a general pattern.

The days tend to blend into one another. Wake up, bus or bike to class, go to internship or job (if they have one), study somewhat, hangout with their group of friends, and if the weekend is on the horizon, go to a party or bar. After every few weeks, study more since the exam is coming up.

I do that too. Maybe I’m just bored.


To fight the boredom, I try to chat with strangers now. That’s the thing that keeps it fresh. It keeps college interesting.

I like making people smile. I like giving compliments. I like chatting for a minute about style. I like teasing and flirting just like a friend would.. I like talking about sports just like a bro would.

Yet nobody understands why I chat with them. They’re fleeting interactions and they’ll go on their way. They’ll go on with their lives.

“Caramel Frappuccino!”

Maybe I’m trying to slightly break their routine. Maybe there’s a moment where they can stop looking at their iPhones so much and talk face to face with a real human being.

I suppose it takes too much effort. Humans are well-known to take the easiest path. Why talk to that cute girl when the cute girl in your clique is easiest to flirt with and date?

Maybe it’s because people truly feel comfortable with themselves. They understand and like their identities. They enjoy the comfort that their clique brings.

It’s not comfortable to go up to somebody random and chat with them. It’s actually difficult, especially in the beginning. There has to be context usually. A friend of a friend or a common interest.

It comes down to the greatest disease of people my age: The fear of awkwardness.

People would rather pass that great opportunity to connect with a stranger than to feel awkward. It’s easier to grab their iPhones and read their Facebook news feed.


Maybe I’m the only one who randomly chats with people.

People don’t understand the openness of the world once you can potentially talk to anybody. It’s adding in the element of randomness. It’s free fun and enjoyment.

Why don’t people leave their cliques?

Because it means you won’t be understood. Belonging is an essential need.

The rush of sadness comes through.

The feeling of belonging and being understood is what I’ll have to give up.

Staying in one clique would be the safe play. It would make my life easier. Joining a club or group would make things infinitely easy.

But I chat with strangers. I enjoy meeting folks that look terribly different from me. I enjoy traveling through people.

It’s a challenge because you may not be welcomed. People enjoy their comfortable social bubbles.

Maybe I’m fooling myself with this whole connectivity thing. Still, it’s worth a shot.

I must keep going to see if it’s possible.

To fall in love with this art form is something few will understand, but this imaginative vision must be attempted.

I smile as I walk out of Starbucks and towards my bus.

Even though I got flaked,


[Disclaimer: This entry is inspired from Sebastian Marshall’s The Million Dollar Question Post. With e-mail permission, I wrote in ode to that amazing piece.]