I have to admit that when I first came to WDC, I was a little overwhelmed by all the options as well... and that was just about seven years ago and the site certainly hasn't gotten any smaller since then!
What I did when I first started out was find two or three contests that I wanted to enter. I made sure that in addition to entering each round of the contest, I also read and reviewed all the other entries, to get to know some other people around the site. Once I felt like I knew the other entrants well enough, I checked out some of the things that they do around the site... usually their signatures or ports will highlight other groups and activities they're involved with, and you can find some great new places on WDC that way, often with at least a friend or two who can help you get acclimated.
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