Day 14: Trying out the funny

First day out with the new focus on having a more fun interaction. I gotta admit, it’s pretty hard to force that (especially when not warmed up / coming from some social setting). But, I definitely do think having a more fun interaction and being more flirty is the way to go. I’m hoping I can become desensitized to the awkwardness of going from not-in-the-mood to that sly fox that exists somewhere deep down.

All told, I think this day actually had my best interaction. It began pretty fast with only 15 minutes of walking around before the first approach. For some reason, I’ve noticed that it can take 30+ish mins to do the first approach (esp. when I haven’t gone out for a while). It could simply be I’m just wussing out…. or may be I need to warm up them eyes.


Her pupils are getting warm. It's a metaphor.


After my first approach that didn’t go anywhere, I saw a girl walking pretty fast (why oh why are the attractive ones always walking so fast). After a pursuit, I started talking to her. It didn’t go that well (I blame myself for not being warmed up). We walked and talked for a bit, but it just never got to a fun point.

Shortly after, I stopped a lady and had what was perhaps my best approach of the whole experiment. I remember it starting sort of as all of my approaches go… A little spark after the directness (though admittedly, I’ve started saying “looked nice” instead of more strongly complimenting looks so as to not inflate the ego anymore). Then it sort of died out a tiny amount, and I remembered I’m trying to be fun now – and started teasing her about her rock n roll shirt or something. Later, s he was looking away, and I called her out on it. I also noticed that I moved myself next to her after we were talking, so it seemed like we naturally transitioned. She had to go meet her brother (who may have been close by… awkward), but we exchanged info! My only thoughts were that I wasn’t as relaxed as I could have been.

Right after that, I started speaking to a super cool girl. She and I immediately hit it off – started talking about lots of nerdy stuff (West Wing fans FTW). We literally shot the shit for 15 minutes. I was somewhat playful. She had a boyfriend and alas we parted ways (note to self: in the future, at least exchange fbook so when bfed folks I obv. get along with are eventually single, we can rekindle).

All in all a great day.

NOW, I just need to get going out consistently again. As a reader has emailed to me, I have no apologies to give – but I do feel crappy because I am sure I will suffer from loss of momentum.  I am *finally* moved into my own place (oh yeah I’d been living with family this whole time. Kind of puts a cramp on the whole dating thing when your only option to take her home involves a tiny twin bed and nods of disapproval from the aunt) and while work is still insane, traveling less. I hope to keep a consistent 3 days a week and wrap up this experiment!… That means I need to do about 5 3-day weeks. I can do this….!


  • 8 approaches
  • 1 follow up


  • Keep having a fun vibe, it works (though may take time to warm up)
  • If you really hit it off and she has a bf, be fbook buds (note – I actually met one of my most attractive fbook friends thru this experiment and fbooking her)


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