Note: Sorry for writing a novel. I need to work on finding a good balance between detail and conciseness as I write these.

Challenge Background

I'm at a watershed moment in my life. I've got some bad habits and fears that are keeping me from living in a way that I feel is honest and authentic. This may sound kind of cliche, but some events in my life over the last 9 months seriously forced me to open up and connect with my emotions (for the first time in my life), and I have this very distinct feeling that what I need right now is massive, committed action.

I feel this build up of energy, like I know that I should take action and at least try -- even if I fail miserably, make A LOT of mistakes, embarrass myself, and probably cause some damage unintentionally -- to sort my life out and start living how I honestly feel I should live, but I really feel nervous and afraid. I’m afraid of being vulnerable. I’m afraid of being alone, and having my loneliness be made worse by acting and making the inevitable stupid mistakes that I will make.

Battling with my fear, however, is my desperation to change the way I relate to my experience of life. Something in me does not want to live in fear and anxiety any more, it wants to act with honesty, bravery, and vulnerability. It wants to be bold, and laugh, and play, and love openly. It wants to relieve me of the tragedy that is a life lived too seriously. Kind of ironically, I seriously want to give everything to this thing in me that wants me to live like this.

It doesn't feel okay to me anymore to be the kind of guy who treats the menu like the meal, or the map like the territory -- I'm tired of reading things about how to improve my life and cultivate a healthy way of expressing myself sexually. So I'm doing something about it. I'm taking action. Today.

Day 3

So none of my friends wanted to go out last night, but I still had to go make my two approaches, so I decided to go out alone. Just the idea of going out alone makes me nervous. I had a vision in my head of me going out, being to nervous to talk to anyone, and just roaming around for the night because I didn't want to be that guy who just hangs out alone at a bar. Behind this apprehension was fear, a fear that I'm not good enough to be liked by strangers -- that I'm not social enough, fun enough, or funny enough to add value to a group of people.

I should add that a big realization that I made in the last 9 months is that I hadn't been a source of fun and enjoyment for myself for almost my entire life -- I was always reliant on someone else or some external circumstance to have fun or enjoy my time. I wanted to change that, so I started going out with no alcohol and really pushing myself to try and self-amuse, let go, and have fun, and I made a lot of progress. I know from the past several months that I can go out without alcohol and dance and talk to people and have fun. This fear I have of not being good enough is bull shit, but it's still there -- I've proven to myself that I can be sober and have fun with friends, but I haven't proven to myself that I can be sober and have fun with strangers. I think going out alone every once and a while will be important for me. Anyway let's get into it:

I put on my NASA shirt, which is a really cool looking shirt and in the past has gotten some comments from people, and leave my house and drive to the street in my area with a bunch of bars. When I arrive I sat in my car for probably fifteen minutes, basically immobilized by apprehension. I sat in my car and smiled for a minute or so and reminded myself that I have total permission to be a blow out tonight. My marker for success is just trying.

I walk around for about fifteen minutes working up the courage to approach someone. In the mean time, I was just practicing good eye contact and body language as I walked around -- I had a very slight smile on my face and I was trying to practice "smizing" #TyraBanks. Actually though, this is an awesome thing to think about and try, in my opinion, if you want to have eyes that appear engaged, fun, and awake. The trick that I discovered if you're wondering "am I doing this right?" is to look at your self in the mirror, and pay attention to how you upper eyelid covers your iris when you have a blank, serious face and when you smile -- what you will find is that when you have a serious, uninviting face, your upper eyelid droops a little bit and covered the top part of your iris, but when you smile, both your eyelids shift slightly so that your entire iris is in-view. Now, don't smile with your mouth, but engage the facial muscles around your eyes that cause your eyelids to lift slightly and stop covering your iris -- now you're smizing.

Anyway, I stop on a corner and texted a friend that I was "shitting my pants," and then I saw a guy I knew and a friend crossing the street. I went over and said hey to them, told them I was out alone, and they told me I should roll with them for the night. I'll add briefly that this prevented me from having to approach total strangers, which is the thing I feel a lot of fear about, but I also don't know these guys too well, so I think it was a good starting place.

We head to the first bar, and I tell them about this challenge. They both thought it was awesome that I was going to try it, and one of the guys wanted to wing with me. This brings me to set #1:

Day 3, Woman #5: Emma

The two guys I'm with grab some drinks and we stand at some bar tables for a minute. I'll add briefly that this is an arcade bar, so there's lot's of old arcade games everywhere. This guy points out these two cute girls standing over by some games, and I tell him I'll go approach and he shakes my hand and says he'll come with me.

This interaction ended up being kind of long, so I'm recalling the conversation as best I can. We walk over and I had no idea what the hell to say. As soon as we get their attention, I lift my hand and kind of point at them, and I was about to say something stupid like "hey, we thought you were both really cute and wanted to come say hi." One of the girls, however, interprets my hand raising as me pointing at the game behind them and asked if we were trying to get to the game. Instantly, I rolled with it:

Girl #1: Are you trying to play?

Me: Yeah, we actually came over here to challenge you two. pointing at Frogger

Both Girls: laugh

Girl #1: Frogger isn't really my game, I'm more of a ski ball person.

Me: (Keeping my feet where they are, I leaned back a little bit in disapproval) That sounds like an excuse.

Girl #1: smiles and shrugs her shoulders

Since this conversation was long, I'm not gonna give the whole thing as a play by play. Here's what happened next:

Then, my wing said he didn't know what ski ball was, and they both laughed and were teasing him about it, acting playfully shocked that he hadn't heard of one of the most popular arcade games ever. This led to us challenging each other to a game of ski ball.

We all walk over to the machines, and my wing and Girl #1 start playing each other. Me and Emma sat at some stools next to the ski ball machines, and I teased her a little bit more about the challenge, asking her if they were going to hustle us or something. After a little back and forth, I asked for her name: Emma; she asked for mine, and I said "Nate," but she misheard it as "Fade." We both laughed, and commented about some weirdly named people we had both met. I then told her that Fade should be name of my angsty, high school age alter-ego -- the part of me that wants to blast fall out boy in the car, and style my hair so that it falls in front of my eyes. She laughed and we talked some more.

She then said that she got reserved a pool table, so we walked over there to set up. She asks me how much pool I play, and I jokingly tell here that I play at least two games a day, even though I've only played pool a handful of times. At this point my wing and Girl #1 come over, and the girls jokingly ask me if I work for NASA because of my shirt. I reply that, actually, I did work for NASA (I'm an aerospace engineer, and I interned at a NASA lab for a summer), and they were all surprised.

As a side note: I don't usually like talking about what I do, and in the past I have refrained from telling anyone what I study and what I'm doing because the context where I can say "I worked for NASA and I'm getting a Master's Degree in Aerospace Engineering" without it coming off as bragging and douchy is somewhat narrow. I've realized in the last year or so that although my ability to do what I have done has come from the intelligence that I inherited, I earned my degree and got to take part in these cool internships by struggling a lot, putting in ridiculous hours, and working my ass off, and that's its not something I should be ashamed of talking about out of the fear of seeming douchy and egotistical. Its a genuinely interesting part of my life that I should share when the opportunity arises, but not take advantage of it to make it seem like I'm better than anyone else.

We play pool, and I keep joking with them, and asked a little bit more about them -- what they studied (both were recent graduates), what their plans were for the summer, etc. Even though I hadn't really played pool before, some beginners luck came through and my first couple shots were actually pretty crazy -- I ended up shooting the cue across the table to have it bounce off a couple walls, and come back at a perfect angle to a ball that I wasn't really aiming for and hitting it in. Emma was like "wtf" and joked with me about hustling her. This happened 3 or 4 times, to the point where I was also like "wtf is happening." I laughed at Emma and pointed at my NASA shirt, kind of implying a rocket scientist would be good at pool.

Anyway, I find out Emma's leaving the country for the summer, and she flies out on Tuesday. Her and her friend were leaving to another bar, so I got her number and told her we should definitely hang when she gets back to the US.

Reflection: This was an awesome interaction for me. The conversation flowed easily, and I felt like I went into a kind of flow where I was able to tease and make jokes pretty easily. It was really good experience to stay in an interaction and actually have fun with someone. In retrospect, however, I didn't escalate. I realized while we were playing pool that although I was flirting with Emma lightly, I wasn't pushing things forward very much, and I wasn't touching her physically almost at all -- the interaction was starting to become more platonic. At the end, I didn't set up the logistics for us to keep hanging out and go to a different bar together. This is definitely something I need to work on.

Day 3, Woman #6: Unknown

Me and these two guys go to a different bar, and they grab some drinks and we sit down at a table. After a few minutes, two fairly cute girls go to the bar behind us. Me and my wing decide to approach, but neither of us knew what to say. I told him we could ask them to settle and argument for us, and we decide to go with that. I ask where my wing is from and he said the east coast, so I said we should tell the girls we're trying to settle an argument about whether the east coast or west coast is the better place to live.

We both walk over, and I touch one of the girls on the shoulder, keeping a little bit more than an arms length between us.

Me: Excuse me, me and my friend are trying to settle and argument, and we're wondering if we can get your opinion.

Girl: Smiles a little bit, but didn't seem super interested Sure.

Me: Okay, so my friend here is from the east coast...

Her: What part?

Him: [State]

Her: No way, that's where I'm from. She's from there too! Points to friend

At this point, this girl's friend turns around from the bar, and gets in the conversation. The three of them talk about their home state for awhile, and what parts of it they were from and what not. One of the girls asks us how we knew each other. My wing replies through a mutual friend, and I add that we had just met that night. I continue, joking, that we had become best friends instantly, and that when we met, we just had the most beautiful moment of eye contact, and that sealed the deal. It was like love at first sight. She smiled a little, but didn't really find my joke that amusing, and I started to get the vibe from her that she thought we were just more guys trying to get with them -- she seemed kind of bored, her body language was kind of closed off, and she wasn't giving much indication of interest.

After a few minutes, I could tell that the interaction was seriously dwindling, and these two girls had friends waiting for them. A guy came over with his phone out and pulled one of the girls away. I tell the other girls that we didn't want to hold her up if her friends were waiting for her, but she stayed and talked to my wing. I left my wing to talk with her, and went back to our table.

Reflection: It was a success just for approaching, and I'm happy about that. I'm also happy that I tried to make a joke during the interaction. I'm not too sure what to take away from this set though, and I'd like your guys' opinion.

General: This was my first night out with a wing man, and that actually worked really well. I've found that, like a lot of guys, I have a lot of trouble coming up with what to say. I find that compliments come pretty easy to me, but I think in some cases, like last night, being direct may not be the way to go. I'd love to hear your guys' opinion on opening in different scenarios, and what kinds of go to situational or observational openers you go for (ie comment about location, girl's body language, etc.), and also how you open with a wing.

Thanks for reading!

3 days down, 47 days to go.