2P Start! (2pstart.com) - 2P Start! is a weekly webcomic and podcast focused on gaming. What makes the site special isn't just the humor and creativeness of the comics, but the rich fan culture that has formed around it. Here's one of their comics (click on it to enlarge):
ThinkGeek (thinkgeek.com) - Thinkgeek is an online store with stuff that all geeks simply much enjoy. Seriously, enjoy it or die. You can't go wrong with some Pirate vs Ninja Batteries! Or how about a Wi-Fi Detecector T-Shirt (It really works!)?
Homestar Runner (homestarrunner.com) - Homestar Runner is a humorous flash cartoon series. It's not meant to be geeky, but if you watch and listen carefully (especially with SrongBad's emails), you may pick up on some nerdy humor.
Woot (woot.com) - Woot is the original deal a day site. A new item comes to the site every midnight for some crazy good price and they stop selling it either the next midnight or when it sells out. That's it. It's that simple. Woot is special because of the humor they use on their site (just read any of the item descriptions) and the community (see the forums).
Now you know where to shopify, entertainificate, and dressilate yourself, all in a geeked-out manner.