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I've been using Omnifocus as a way to keep track of running events I might want to check out, plus just general ideas of interesting things to do (art stuff, theatre, etc). If I find myself with a little free time, I can just open my "NYC things to do" single-action project and start looking around. I put all the relevant info right there in the note field so it's with me whenever I open up OF on my iPod Touch. And if something's time-limited, I just put start and due dates and it pops up in my "due soon" perspective so I don't miss it.

For "contexts" I use people I want to do those particular things with, if applicable. So if I'm with that person I can just look at their context and see some things we might do together.