What's less romantic: Buying something practical or buying something generic? Roses are right out. But can a gadget be sweet?
First thing's first: I'm a guy. So I'm going to speak to my fellow men here. If the demographic reports are the least bit true, men make up the majority of our readership here.
And if my personal experience is any measure, it's men who need the most help buying Valentine's Day gifts in the first place.
That said, let's remember the fundamental operating principle of all intergender relationships: Women are more like men than they are dissimilar. As the sage relationship counselor Miranda Lambert once advised men on the prowl, "We're just like you. Only prettier."
And if you're gay, I suspect most of this still applies. Gay folk might have it slightly easier since they're buying for the same sex, but they still need to get the romance right. If you're buying for someone transgendered, they already told me what they want for Valentine's Day, and it's that you stop calling them "Optimus Prime" in bed.
First Things First

Okay, answer me this: Are you buying something for a long-term partner or someone you're trying to woo? That'll make a big difference in the sort of gadgets that might be appropriate.
I asked some friends for their input.
Long-Term Has More Leeway

"Kourosh gave me my MacBook Air and an iPhone for Valentine's Day two years ago. Best gifts, best hubby ever!" said Kristen Philipkoski.
Now it didn't hurt that those are pretty spendy gifts, which, let's face it, amps up the romance in the right situation. Especially in long-term relationships, where it shows you're still in it to win it and big gifts don't come off as desperate.
But don't miss the most important thing: Kourosh bought Kristen two things that made her daily life better on an ongoing basis. He didn't just drop a couple of grand to impress—the large amount of money showed his confidence that Kristen would love her gifts. You can take this sort of risk when you're in a long-term relationship because you should have a good idea what sort of things your partner would really use.
Be careful, though! I once bought a girlfriend a sewing machine for her birthday, a gift she'd claimed she'd wanted for years. But when she never got around to actually using it, I couldn't help but be hurt. That was on me—but just be aware before you invest too heavily in gadgets that imply that you want your significant other to change their behavior or which have a built-in fail state. (Which precariously includes most gadgets.)
Another pal, Ghostpony, warned, "I once bought my girlfriend a ricemaker for Christmas. Let's just say it didn't go over well. In my defense, it was a Zojirushi."
If you have to explain to your girlfriend why the gift is really special, you're off target—buying for you, not her.
If You're Still Getting to Know Her

No matter how much money you're ready to spend, keep it modest. Under $200, probably. And less is probably better. Lots of little gifts with which you can keep surprising her are probably the best.
iPods are a perennial favorite, but don't let Apple guilt you into spending too much. A good rule of thumb for buying women gifts while you're dating is to never spend so much that you're going to make them even begin to question that you're trying to buy their affection. Better an iPod nano than an iPod Touch, unless you're sure they really would rather have a Touch.
If she's already got an iPod of any sort, skip it. Sorry, but it's just too thoughtless. In fact, I think that's important enough to bold: Never buy her an upgrade.
Besides, if the relationship never goes anywhere—likely—you won't feel like such a rube for spending too much money on a token.
Point-and-shoot cameras tend to go over well. Plus you can use it right then with her, which is a huge bonus. Especially when she's taking pictures of you doing other romantic things.
Kindles and Nooks show that you have noticed she can read, or at least enjoys the way the squiggly shapes make her brains feel.
Try to keep it physically small. My gut feeling is that smaller, well-designed gadgetry is more "feminine" than something that's pink or red. (Correct me if I'm wrong, ladies.) Plus, it makes it easier to...
Present the Present Properly, Poindexter

Valentine's Day presents are about sending a message. "Hey, human. I enjoy your unique composition and would perhaps like to copulate in the future." (You can use that on your card. No charge.)
Take whatever you're giving out of its package. Unwrap the packing gauze. Charge the batteries. Load it up with music or apps or flash memory if it needs it. And by god, put it into a cute box or—if you must—a gift bag. You can make a cordless screwdriver at least borderline romantic if you put it in a nice box. (And if you're incredibly good looking.)
However! Save the box and receipt somewhere else just in case! Don't make a big deal out of it, but if you can tell she's really not into it you can gently let her know that you wouldn't be hurt if she decided to exchange it. Most stores will do gift receipts throughout the year, too, not only during the holidays. Wait until the day after, though.
Here's the Real Secret

While the principle applies to gift-giving in general, it's ten times as important during Valentine's Day: If your gift doesn't show that you've been paying attention, you have failed.
You can ignore everything else I've said if you just get this one right. Has she talked about really wanting a DSLR? That trumps my "keep it small" suggestion, provided it won't be so expensive that it sends you into creepy attempted sugar daddy territory.
Heck, find her a nice used one and good 50mm lens on the cheap. The more your gift evidences your forethought and effort, the better it is.
A corollary: If you're not sure that she'd like a gadget as a Valentine's present, you might not even need to buy her a Valentine's Day gift. Are you sure she's expecting one from you?
Post-Gadget, Combo with Tradition

So flowers, chocolates, trips to the spa or weekend getaways? All the "romantic" stuff that just screams "I have no idea what to get you so I got you this baseline item"? That stuff is totally great in conjunction with a thoughtful gift. Give her an iPod because she lost her last one—and flowers. Give her a camera—in a box of chocolates. Fill up her Kindle with awesome ebooks—then send her to get a massage. Alone. (Sorry, but couple's massage isn't as relaxing.)
(While we're on the subject: every woman in the world loves flowers. I don't care how many times you've heard her say, "Oh, what a waste flowers are!" Even if she really means it, she'll still be completely charmed when you hand her a bouquet. Any women who disagree with me should send me their address so I can send them flowers.)
(Oh, I closed my parenthesis before I got to the most important thing about Valentine's flowers: Never, ever red roses. White or pink roses if you must. But lilies, tulips, orchids? Invariably a better choice. Ask your florist to make you something special for her. They do that, you know. Red roses are for toreadors and pimply junior high dancers.)
An Idea for Next Year

There are tons of great gifts available on Etsy. But did you know you can get the Etsy crafters to make you a custom product? Etsy Alchemy is like an inverted eBay: You describe what you want; people put up proposals and bids; you pick the one that seems best.
What's clever about this is that, as a human process, Alchemy can be used to outsource your gift-giving and romance ideas. I've put up requests before that only described the woman for whom the gift was for—but made no mention at all of any specific item. Dozens of folks sprang into action, suggesting items she might enjoy based off of my description. Outsourced romance is the future.
A Final Warning: Sex Gadgets

This one is easy: If you live together or are in a similar long-term situation, these are fine. If you've just started sleeping together, avoid the toys. I think buying sex toys for a partner can be really sweet, but the inherent sexual underpinnings of Valentine's Day sends it over the skeevy top in a new relationship. It's like bringing a toothbrush on a first date.
Good luck, romantics! If my help gets you lucky, you know where to send the JPGs...
...to the National Archives! Thanks to them for the above picture. Nothing says true love like winning a dishwasher.


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