The 5K at SW was probably one my favorite social, "on the side", parts of the conference (aside from the BBQ on the SCALE boat - f*%#, that was good BBQ lol). I met a few other people I hadn't met before and connected. I even got lost and did 2 extra miles with one of them! lol.
Anyway, yeah the dichotomy thing is at epidemic levels at SpiceWorld now. I've been to 4 of them over the past 5 years (missed one for my wedding in 2013), and I still sometimes feel like an "outsider", and that can be rough. I always try as hard as I can to get involved and such, but it can be hard for me at times (e.g. not knowing what to talk about, not knowing what to bring up, is what I'm saying stupid to the other person, am I not talking enough, etc...). For example - I've met Grey and spoken to him no less than 8-9 times and each time, he has no idea who I am. Same goes for people like Bob Beatty, Phil Moya, etc... It doesn't make them bad people - far from it, I think they are awesome. It just makes me second guess myself, like, what am I doing wrong that these people I've met and spoken to on multiple occasions don't remember me worth a damn? lol
Some people are just more socially engaged than others and you'll never get away from that in IT I think. I work with 50 devs as my users and 99% of them are completely socially awkward or SUPER introverted. It's just the way they are. IT folks aren't like that, usually, but there are some that tend to be.