First thing: Check the newspaper for deals, deals, deals
Stores like CompUSA, Best Buy, Circuit City and others are running some pretty spectacular sales these days. Some are one-day-only, so be prepared to get up early, take a long lunch or brave the crowds to take advantage of them. Be prepared to do the rebate paperwork afterwards -- it's really not that bad.
I just picked up stocking stuffers for a sturdy stocking,at CompUSA: some pretty dandy computer speakers for $25; a 250 GB hard drive for $6; and 100 blank CDs for $10. That's after the rebate, of course.
Straight-up technology gifts
It seems incredible, but some authentically geeky people don't have USB drives. Or they got theirs years ago when 8 MB was cool; these people clearly need a 1 GB or larger USB drive. A really great gift would be this combo Swiss Army Knife/USB drive, offered through ThinkGeek.com.
If your geek is heading out of town for three weeks, out of the next six, and you'd like to keep in touch, then consider webcams. You can keep in touch visually, as well as on the phone. Creative seems to be the most popular brand. From my reading on Amazon.com, you should probably spend at least $40 on each cam.
Your geek might not have a good laptop bag, especially if she just uses a leftover bag from JavaOne or another conference; it might be worn out, too big, or too small. Try looking around for a better one; TiBags are pretty cool. If your geek travels, try to find a good compact one with wheels.
Anyone who's on the road can use an extra laptop battery, too.
If you're totally at a loss, just go to Circuit City or Best Buy and get a gift certificate. Throw in a sci-fi book or a DVD to show you totally didn't give up, or else throw in a bright orange scarf, to make the recipient all the more grateful for the customizability of the gift certificate.
Gifts for the Mac geeks
Mac is the big rabbit-hole of ideas in and of itself. Books about Powerbooks; cool screensavers; cute, well-designed laptop bags; and all the cool-looking accessories are something to consider. Two articles on Mac-specific gifts are on the Mac site, by Derrick Story and Terrie Miller.
i-Pods all over the place
Speaking of Apple, you probably don't need me to tell you about iPods. My dad even knows what an iPod is. No list would be complete without it. Apple will engrave iPods for free, so keep that in mind. One thing your iPod-owning geek might not have is speakers that work for the iPod and computer. Derrick Story's article provides a recommendation.
Gifts for the Linux geeks
This depends on your geek, but if he or she likes to experiment, check Distrowatch for what's new and hot. Knoppix Hacks has been getting a lot of buzz. Here's another couple article on gifts for the Linux crowd, or geeks in general.
Books and book gift certificates
If you know your geek is really into that "Linux" thing but that's about it, a chunky-sized gift certificate for the procurement of technical books will go over well. Rather than becoming bland and general with a gift certificate from Amazon, try one from your local technical bookstore like Powell's, Digital Guru, SoftPro or Nerdbooks.
Be sure to personalize your gifts. Any time you give a gift certificate, augment with something physical as well like a USB drive, a DVD or a boomerang.
A Netflix membership might be a good idea for the geek who loves Jim Jarmusch, Jacques Tati or every "Stargate" episode, all of which are unlikely to be found at Blockbuster.
I personally love my portable DVD player. The prices are coming down to within the $100 range for a seven-inch screen. Granted, anyone with a laptop can probably play a DVD in it, but sometimes you don't want to bring your laptop on a ski trip or to the gym. Also, if your geek is going to be watching it with multiple people, be sure to get enough jacks, good headphones with long cords, and/or good speakers. That'll give all the geeks a good viewing and listening experience. Sometimes, the audio on DVD players is barely loud enough.
Do a little prodding to find out what your geek's favorite childhood shows were. DVDs for nearly any show are available now. In geek circles, I hear repeated mentions of SpeedRacer and HR Puffenstuff. It's all out there. Of course, a season or two of MacGyver on DVD would probably go over well with nearly anyone geek-oriented.
Toys, games, and puzzles for geeks of all ages
Geeks like to figure things out and take things apart. (Occasionally, they'll put them back together again.) So, you'll make a hit with some other gifts not related to computer area .
It's likely that at some point in his or her past, your geek played Dungeons and Dragons, Magic: The Gathering or another role-playing game. It's not easy to play on your own, but do a little subtle investigation into what your geek's former and current interest is in these games and consider buying something in that area.
If your geek currently plays Dungeons and Dragons, find out what kind of character he plays -- paladin, cleric, etc. -- and get a book on that kind of character. Also, consider getting a game that can be played with non-Dungeons and Dragon people, such as Steve Jackson's Munchkin or another Steve Jackson game.
You can also jump on the Sudoku bandwagon. Be sure to get the ultra hard puzzles, since the beginning and intermediate levels are fairly easy.
If you listen to National Public Radio, you've probably heard Will Shortz talk about the World Puzzle Championships. You can get a collection of the puzzles for those contests in various bookstores; here's one on Amazon.com. These are likely to be very difficult. I looked at the qualifying test, and it pretty much made my brain spin. This one seems reasonably easy and comes from a collection of the puzzles Shortz does on NPR.
There are a million puzzle possibilities, so just go with the theme of logic puzzles and see where it leads you.
For stocking stuffers or just for fun, try going to your local high-end toy store, such as Into the Wind in Colorado, and pick up some rubber frogs, Play-Doh, Silly Putty or boomerangs. If your geek doesn't take himself or herself too seriously, a propeller beanie is a fun, silly gift, too.
It's hard to go wrong with ThinkGeek.com
Thinkgeek.com is a great geek gift resource. The t-shirts and books are almost universally funny. For serious geek stuff, you should be able to find what you're looking for. It's a little late for online shipping, but one should give it a try.
I do like one humorous geek item that's not on ThinkGeek.com: the geek gift flowchart. Cafepress.com also offers t-shirts and mugs carrying slogans such as "Half Bad Boy Plus Protocol" and "Encapsulated Big Fat Opening."
A plug for my book: Dating Design Patterns
If your geek does software programming or design, Dating Design Patterns might be up his alley. It's a spoof on the Design Patterns book by the "Gang of Four" (three, sadly, since November) and applies the principles of design patterns to dating. Alistair Cockburn, author of Agile Software Development, stated that while reading it, "I laughed so hard, I dropped my copy in the bathtub." The book is available through Amazon.com, Thinkgeek.com and Cafepress.com.
About the author: Solveig Haugland is the author of "Dating Design Patterns," a book with a different take on how design patterns came about and "She'll Love It: The Guy's Guide to Giving Great Gifts." Solveig is also the author of the OpenOffice.org Resource Kit, StarOffice Companion and writes for TechTarget on OpenOffice.org. Check out her OpenOffice.org blog and her gift-giving and geek humor blog.