Meeting IRL. LOL. OMG!
The very first time I can recall meeting someone in my modern online era was when I met Dave and Dan, two fellows from MetaFilter, at Duke of Perth on the north side. It ended up being a great time. A little initial awkwardness, but then, just great.
Shortly after that, regular Chicago Bloggers meetings started up. It was a group of us, about 10 or 12, including local people whose work I totally admired. We met regularly, planned out projects, had food and libations, and eventually launched an online magazine called No East.
Gapers' Block, the Chicago powerhouse, also sprung indirectly out of those meetings.
Really since then, I've been a lot more comfortable meeting folks I've "met" on the internets. I'm looking forward to Webvisions next month, of course, because I'll finally get to see a lot of the people who have inspired my work.
And Ryan.