It's one of the sad truths of the Internet that I don't remember how I found most of the websites that I now consider indispensable. I can only guess that it was aimless surfing or Googling or maybe someone pointed it to me. The oldest mention in my email is this Holyland post in May 2004, although the context leads me to believe that I was already a regular lurker at that point.
Taking a risk and inviting strangers to share a hotel room at E3
In 2006, a High School friend who lives in California managed to snag about a dozen spots on a list for E3. A bunch of us made plans to fly out there and have a great time being massive nerds. A few months ahead of time, I saw this AskMe asking for couch space in LA for E3. (This sort of thing would probably be completely Frowned Upon now.) I'm not sure why it took me a week, but I finally offered boo_radley and his friend bed/floor space in the two hotel rooms we had booked right next to LAX. I had never met him, nor even talked on the phone before we shook hands in the lobby of the hotel. But we had PlayStations and NintendoDSes in our luggage, and spent four amazing days playing video games 20 hours per day.