I suck at giving gifts, but no more. Surprise.com looks to be a godsend for me. They have gifts organized by occasion, person, and most importantly, by personality/hobby. Some of the personality/hobby categories are: A Little Bit Country, Krispy Kreme Maniacs, Environmentally Responsible, and Former Midwesterner. (Thanks, Al!)
As a side note, Surprise.com gets its links from site visitors. A good idea. A better idea would be to give each user a weblog. People publish gift links on their Surprise.com weblogs, categorizing them as they go, and those links are fed back into the main system (after being approved, of course). Not many of the weblogs would get utilized or read, but the few that did (most likely run by people like Cory & Mark, Drue & Shauna, or Zannah, who are expert at digging up such things) would bring a lot of traffic, interest, and links to the site. It's dmoz + Epinions + weblogs, a mix that could yield some interesting results.