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 6

I'm beginning to realize that the logistics of this challenge are... challenging. My day to day life puts me in an area where there certainly are girls, but not in an area where approaching is possible directly. I work as a research assistant at a university, so there are definitely cute girls taking summer classes here, the only problem is that they are only on campus from 9-5pm, which are the exact hours I'm stuck inside a building writing code.

Having only approached one girl today, I spent almost two hours going from a grocery store to target to the outdoor mall in my area looking to get my other approach. I didn't see any girls at the grocery store or target (it was kind of late in the evening though), and the cute girls I did see at the outdoor mall were nested in groups of people or were obviously there with a SO.

I'm now 3 approaches behind for the challenge. Given that day time logistics are tough for me, I may have to settle for 1-3 approaches during the day, and play catch up on the weekends. I think modifying my approach to this challenge in this way could be beneficial though -- one of the things I really like that Mark Manson talks about in Models is honesty, and approaching honestly is probably the single most important thing to me. I'm not out here to "practice picking up girls," so to speak, but to approach women I honestly find attractive, build courage in the face of vulnerability, and develop non-neediness, as Manson would put it; and to be honest, going out of my way and spending 2+ hours looking around for a girl to approach just to meet my quota for the day feels super needy and inauthentic.

I'd rather put my effort into slightly re-organizing my day so that the approaches can happen more naturally, and I could really use some advice from you guys on that front. I'm thinking maybe I take two 10-15 minute breaks in the morning and afternoon to take a walk around campus -- it'll be a good break my work and present me with more opportunities to approach. Additionally, maybe I park on the side of campus farther away from my building (not that much farther, maybe add another 5-10 minutes to my walk) so that I have a little more time outside before I get to my building.

I'll have to experiment with this, but I'll make sure I keep you guys posted on what I try. Maybe this can help out some of you in a similar situation.

Anyway, let's get into the day.

Day 6, Woman #9: Unknown

I went to a library on campus to do some work, and when I sat down I made eye contact with a familiar face -- I saw a girl I knew from track back in high school (she went to a different school), but I've never really talked to her and haven't seen her in years. She was about to leave, so I packed up my stuff and walked over to her and friend who were sitting at a table.

I'm not gonna give the play by play on this conversation because it was pretty short, and she was neutral/disinterested in talking to me. I asked her if she pole vaulted back in high school, and she said yes, then I proceeded to ask her some catch up questions (does she still do it, etc.), but she was giving short answers and obviously wasn't interested in catching up. She said it was cool to run into me, then she left.

Reflection: The success here was just in doing the approach, especially because that's the part I'm still having trouble with. I don't think I necessarily did anything wrong here either, she just wasn't receptive -- no big deal.

Confirmed Date with Shannon

So I texted Shannon from Day 2, and we set up a date for tomorrow. The conversation went as follows:

Me: Hey, Shannon! It's Nate!

Me: I have a super important question for you

Her: Yeah what's up!

Me: How do you feel about fun dates with cute boys?

Her: Honestly I'm more of a boring dates with ugly boys kinda gal, but I guess I could mix it up!

Me: hahah You free tomorrow around 8pm? Let's grab some ice cream at [local outdoor mall]!

Her: Yeah!

And the rest is logistics. I'm excited because I'm actually looking forward to going out with this girl -- this isn't something I've felt recently, or very many times in my life. She's super cute by my book, and she seems pretty cool. Wish me luck!

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Journal Archive:

Days 1 & 2

Day 3

Day 4

Day 5