Facebook's Achilles' Heel Revealed?

Cory Doctrow has written an interesting piece for Information Week in which he describes Facebook’s downfall as well as the downfall of any social network. According to Doctrow, “Adding more users to a social network increases the probability that it will put you in an awkward social circumstance.” I completely agree with this being one of the primary downfalls of many social networks.

The only flaw with this theory is that each of the social networks can develop tools that make the socially awkward moments less likely. Features that include the grouping features that I have been touting for the past few months as well as advanced privacy settings similar to the ones already provided by Facebook. As social networks evolve, systems will be put in place that protect the users and eventually we will have access to close to perfect social networking tools similar to the ones envisioned by Cory Doctrow’s fiancee:

My fiancee once proposed a “social scheduling” application that would watch your phone and email and IM to figure out who your pals were and give you a little alert if too much time passed without your reaching out to say hello and keep the coals of your relationship aglow.

I have been looking for this type of tool since I read the book “Never Eat Alone” by Keith Ferazzi in January 2006. Looks like I should have just gone out and built the system since it still hasn’t been built. I have a feeling that the new mobile SDKs being provided by Apple, Verizon and Google will help us build a social scheduling application that integrates with existing social utilities.

Regardless, I think Cory’s article is accurate for the social networks of the past (and a few present) but the problem that Cory portrays won’t exist in future social networks. Do you have any socially awkward moments that have forced you to consider leaving Facebook?