Morendil comments on Hacking Less Wrong made easy: Vagrant edition - Less Wrong
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Which version of Ruby do you have? Macs ship with 1.8.2 (Tiger), 1.8.6 (Leopard) or 1.8.7 (Snow Leopard).
The advice I've seen for this error is to get the latest version of Rubygems, not Ruby: http://rubygems.org/pages/download
Right, it's more likely a problem of the version of gems and not of ruby (I think I have Leopard - I'm not on my home machine now).
When running
... I got the same error as above, so I guess I'll have to manually download it and install it and hope that the new one will become the default version (I'm somewhat wary of doing that, I don't like having several versions of the same software on one machine).