I've been searching around a bit and still haven't really found much on the issue, so I decided I would post here.
A few times a day the Shockwave Flash plugin for Chrome crashes on any website that uses it, and I'm not exactly sure why.
It has crashed using Facebook, Grooveshark, YouTube and other websites.

Does anyone have any ideas?

You have to update your machine and re install "Google Chrome" or clear your whole browsing history. Also, try re installing flash or updating it if you haven't yet.

Update my machine as in drivers or hardware?

Chrome is up to date and I did just reinstall flash, so we'll see how that works, however I don't think it changed the version that Google Chrome uses.