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 7 - The Date

Okay, so first off I didn't successfully approach any girls today -- I spent my entire morning inside and skipped lunch to finish a presentation I had to give in the afternoon. I ended up doing really well on my presentation, so that's pretty cool by itself. Anyway, I finish this presentation, get lunch, and go back to campus for about 30 minutes to try and do my approaches before I go to the gym and get ready for my date.

You know that saying that each level has a new boss? That's what I'm experiencing -- if I have a few minutes to work up the courage to approach a girl who is sitting down somewhere, I can do it, but just spontaneously opening my mouth when walking past a girl is showing itself to be another anxiety block. I walked around my campus for those thirty minutes and I panicked out of approaching a couple girls. Feeling kind of frustrated, I went to the gym and went home to get ready for my date with a girl from day 2.

I show up to the date (ice cream at local outdoor mall), see Shannon, walk up, give her a hug, and walk inside the ice cream store. We're talking and keeping things light, and the mindset I was in was that of familiarity -- how would I talk to her if she were one my long-time friends?

Side Note on Familiarity: I mentioned in an earlier post that I've spent a good amount of my time going out this last year focused solely on self-amusement. I realized I wasn't being my own source of fun and enjoyment or being very social -- I was relying on alcohol for that -- so I went out sober and learned how to have fun with people without alcohol. I did that (and I now prefer to go out without any alcohol, although I occasionally will have a drink or two), and one of the times I went out dancing, I met this incredible girl named Amy -- a stunning red head who was a great dancer, and she was hilarious and incredibly fun. I honestly don't think I've hit it off faster with any person in my life -- we absolutely "clicked." I end up finding out that she was in a relationship of almost 5 years (her BF is a super cool guy), but we became good friends and hang out regularly now. When I think of familiarity, I think of how I feel when I hang out with this girl. From the minute we started talking, it was like we'd been long-time friends and genuinely enjoyed each other's company, and that vibe hasn't gone away. I'm completely myself around her, and she thinks its hilarious, and vice-versa. That's what I channel when I meet new girls/people in general.

Anyway, back to my date: me and this girl kind of hit it off, and we were obviously attracted to each other. We walked around the mall for about in hour and talked, then I asked her if she had any plans for the rest of the night, she said no, so I told her we should go get some beer and watch a movie at my place. She agreed, and we left.

We get to my place, have some drinks, and start a movie. The physical contact barrier hadn't totally been broken yet, so I used stories as an opportunity to do that. We we're talking about scary movies, so I started telling this story of how I watched the Grudge when I was 7-8 years old and it scarred me for years. Just prior to getting into the story though, I told her something stupid with a smile on my face like, "This story is traumatizing -- I think I'm gonna need you to hold my hand." From there, the physical stuff escalated. She's a talker during movies, and she told me that if she's talking to much that I should just tell her to shut up. We're cuddling and she's talking, so I tell her to shut up and I kiss her. We make out, I fumble miserably getting her bra off (remember the virgin thing? lol), but I totally owned it and made a stupid joke about my worthless aerospace engineering degree. She laughed and took her bra off, then I took my shirt off and we kept making out.

Eventually, things started to get very sexual, and she said she had bad news, and that it was the only bad news a girl could have. I tell her, laughing, "no worries, there's no bad news tonight" then kissed her again. We end up hanging out, cuddling, and talking in my bed till like 2am, and then I drove her home. I didn't bring up my virginity, although I will if we hang out again and things get sexual. Being honest is super important to me, and I want her to be able to make the decision about whether she wants to take someone's virginity. If not, no worries.

Day 8 - Symptoms

So once again I didn't have an successful approaches on Thursday. I was busy working during the day, then I had a Capoeira class at night, but I was going out with some friends afterwards, so I figured I do my approaches there.

One of the things I need to add in here, because its relevant, is that I started taking a medication (Propecia/Finasteride) last week because I caught early signs of a receding hairline and I'd like to keep my hair as long as I can (I'm 21). If you're not aware, finasteride prevents your body from converting testosterone into the more potent hormone Dihydrotestosterone (DHT) (DHT, on some level, is responsible for the systematic death of hair follicles known as male pattern baldness), so it screws with your hormones and a lot of guys get mild side effects, and some small percentage of men get severe side effects that don't get better after stopping the medication (depression, ED, loss of libido, etc.). It's a super controversial drug, even though most men (70-85%) don't get any negative side effects.

Anyway, I've been having side effects since starting the drug, and they've gotten worse over the week: I've noticed a significant decrease in my libido these last two days; I've been having trouble concentrating; I've been losing my train of thought when talking, which is very unlike me; it feels like my blood pressure is low (like I just ate thanksgiving dinner and stood up too quickly, but all the time); I've been having mood swings (only from neutral to negative emotions and back); I'm having trouble falling asleep at night (I haven't had insomnia in years); and I have waves of fatigue/tiredness (possibly due to insomnia). I've since stopped taking the drug and I'm going to see my GP to talk about continuing/quitting the medication.

But as of this day, I'm on the medication, and I went out with my friends even though I wasn't feeling well -- I thought going out, moving, and talking to people might make me feel better. However, after going out, I started getting waves of tiredness and I really didn't have any interest in talking to girls. I end up calling it a night and heading home.

Day 9 - More Numbers

Day 9, Woman #10:

I'm feeling much better in the afternoon today, and my friend that I mentioned in the familiarity section in Day 7 invited me over to have a wine/movie night with her and a bunch of people. I go over, and one of the girls who came over was stunning -- super cute yoga teacher, smart, and gave off this incredibly kind vibe. I talk to her for a while through out the night but she was a little on the shy side and I had to do a good amount of the work to keep the conversation funny and interesting. This was a good challenge, and I actually enjoyed it -- in the past (meaning several months ago), I wouldn't have been able to keep a conversation going even if I wanted to, let alone keep it funny and interesting. I surprised myself that I was doing that, and I think it's a good sign that I'm becoming more socially capable and comfortable.

Anyway She gave some IOI's throughout the night, particularly with eye contact -- I caught her looking at me when everyone in the group laughed about something, stuff like that. We're all about to go to the bars and dance, but she has to teach a yoga class in the morning, so she parts ways. After she says bye to people, I tell her to wait up, and I catch up with her:

Me: "Hey, I have a question for you."

Her: "Yeah?" and keeps walking.

Me: I walk next to her and say, "How do you feel about fun dates with cute boys?"

Her: She stops, turns to me smiling, and laughed a little. "Well it depends what you mean.."

Me: About to respond

Her: "I mean, I'm kind of seeing someone right now, but it's not serious..."

Me: Smiling, "I'll tell you what, let me get your number and we'll figure something out."

She agrees, so I get her number and we part ways.

Reflection: I'm into this girl -- she's very "my type." I've never been in this kind of situation though, where a girl says that she has something with another guy even if it's not serious. I feel as though I should just treat it like any other situation -- she was interested, I got her number, so I'll text her to set up a date and see if she wants to meet up. If she's interested, she'll come; if she feels conflicted and says no because she's seeing someone else and she likes him, then good on her for being honest with her values, and no hard feelings. Honestly, her standing up for her values would only make me more attracted.

Day 9, Woman #11:

I get to the bars, and while in line I run into a cute girl I had a class with a long time ago who just recently turned 21. I was already in a fun, social mood, and I greeted her enthusiastically. She immediately hugged me (keep in mind I had a class with this girl, but we never really talked) and started asking me questions. I had just passed the bouncer and I was kind of in the way of the entrance, so I told her I would see her inside.

I'm on the dance floor and she comes in with her friends. We see each other, and she hugs me again and we talk. I ask her if she's around for the summer, and she says yes, so I tell her we should hang out soon. She gives an enthusiastic "Yeah!" and I ask her for her number. She gives me her number, we talk a little more, than she goes back to meet up with her friends.

Reflection: This wasn't a pure cold approach since me and this girl met each other a few years ago, but we talked very little throughout that class, so I wouldn't even classify her as an acquaintance. The thing that stands out to me about this particular interaction is that the interaction flowed incredibly smoothly. I'd been having fun all night, and just got a girl's number, and this other girl basically just came over and hugged me. I was showing how much fun I was having with my smile and my energy, and she just seamlessly joined it. It was pretty awesome.

This also goes to show the value of surrounding yourself with people you enjoy spending time with also. I was having a lot of fun with the people I was with, and it showed.

General: So due to some external circumstances (work, medication side affects and feeling shitty) and some anxiety on my part, I haven't been able to keep up with approaching 2 girls a day. Another factor that's playing into this is honesty, though -- I don't want to approach a girl that I'm not honestly interested in just for "practice." I don't like this idea of treating people only as a means to an end. Obviously, I am engaging with women with the goal in mind of becoming better with women in general, so in that way the women I approach are a kind of means to an end, but I can also do that in an honest way, where I approach women I am honestly attracted to and genuinely interested in getting to know better.

With that being said, I won't force myself to approach a women I don't honestly find attractive and express sexual interest just to meet my quota for the day, even if that means not getting to 100 women by the end of 50 days. I'm still committed to approaching however many attractive women I see, however.

Thanks for reading!

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Journal Archive:

Days 1 & 2

Day 3

Day 4

Day 5

Day 6