Hey, someone on MetaFilter found my gift-giving advice posts and linked them! This is both exciting...and made me realize I needed to get a move on for this year's helpful gift shopping post. Thanksgiving was really late and I was sort of surprised today to realize how little time left there is.
So, to recap: sometimes, you have to give gifts to people you dislike, because your family dynamics or unwritten workplace rules require it and not handing over something wrapped up in a box or gift bag would be a THING, and it's worth spending some money (as little as possible, of course) to keep the peace.
The basic principles are the same every year. (1) Cheap, but untraceably cheap; if you buy them some bad wine, it can't be Charles Shaw, because everyone knows that was only $3. (2) Minimal effort; should be something you can buy on your other errands or order online with everyone else's gifts. (3) Something you might have plausibly thought they might like, since if you wanted to be confrontational you could have just refused to buy them anything.
As always, I want to note that I don't shop for anyone I don't like -- this annual series came out of hearing a lot of friends talk about the annual trauma of buying something for their obnoxious BIL or their least-favorite coworker they somehow drew for the office Secret Santa. If I do give you a gift, and you hate it, I swear it was accidental. The vast majority of bad gift-giving is accidental, which of course is the cover you need for your deliberate bad gift.
This year's theme is "Almost Generic." Even more common than the "I really don't like this person" problem is the "I really don't know this person all that well" problem, which is why every store from Walgreens to Macys is loaded up with the sort of generic gifts that satisfy a general recurring need in some way, or accomplish some common yet specialized task in a more-efficient way. (Key chain fobs that will talk to your smartphone and tell you where your keys are! Freezable wine chilling tubes!)
Gloves, Scarves, Hats
If you live in a cold climate, you probably go through a fair number of gloves, hats, and scarves, because this stuff gets lost a lot. It also gets dingy over time. Some people like to have multiple sets in various colors to coordinate with outfits. (I care about color only in that I've started buying all my gloves in pink whenever possible, because Molly won't borrow pink stuff.)
Here is a very inexpensive "cashmere feel" acrylic scarf that can be dropped into a gift bag and presented to just about anyone who doesn't live in Miami as a perfectly acceptable winter gift. Available colors include traffic-cone orange and a shade of purple that will only appeal to people who truly love the color purple. This scarf is cheaper and available in some really unappealing moss greens.
You could also give these budget-priced leather driving gloves" which, according to the reviews, will fall apart within days. They're also available in a women's style; these are better reviewed overall aside from not fitting people with adult-sized hands. (Note: you can't actually order these for this Christmas; they're shipped from China and won't come from January. However, low-quality leather driving gloves are available all over. If you're trying them on in person, you can pick some with a scratchy tag and a stiff feel.)
For a hat, look to Land's End. Usually, they're a source of high-quality merchandise, but the reviews for their fleece hats complain vehemently that they are too small for adult heads.
Slippers are a classic Christmas gift. Who doesn't like a nice pair of slippers? The thing is, most people have some fairly strong preferences, first among them clog-style vs. NOT. Think about the shoes and slippers you've seen your recipient wear in the past. If they're full-coverage, go for clog style slippers: men's women's.
Wallets are one of those "you had one job!" items. You carry it in a pocket or a purse and it's supposed to hold your credit cards and cash so they don't fall out. This one is apparently oversized and made of unattractive materials (but one of the reviewers will also assure you that it's "manly," so no worries about the "purse" bit in the description.) This one is apparently put together in such a way that if you don't fill it up, your stuff will fall out, and if you do fill it up, the clasp won't snap. (Alas! You won't be able to get that one for Christmas this year -- it's shipped from China and they don't appear to have a "priority shipping" option that would get it here in time.)
I have a friend who fixes watches for a living. He will tell you that a Timex is better, in the sense of accurately telling time, than any expensive watch; expensive watches are mechanical, cheap ones use a battery, and battery-powered watches keep better time. (The purpose of a Rolex isn't really to tell time, obviously.) Anyway, you're obviously not going to buy an expensive watch for someone you don't like. But you could totally buy a fancy-looking watch for less than $10 (or this manlier-looking model for under $15.)
You could also give someone a watch that requires you to tap the screen before it actually tells you what time it is, or this weirdly badass-looking model which claims to be water resistant, totally looks like it ought to be water resistant, and according to reviews, is not even remotely water resistant. Finally, this one is outside the usual price range I shoot for, but
if you're willing to budget $40, you could give someone a world of frustrationwith an alleged smartwatch that arrives with poorly written instructions badly translated from Chinese, that relies on an app that may or may not actually exist, and has been known to break after two charges. (Note: go to the "other sellers" and find someone that's offering it with Prime Shipping -- if it ships from China, you won't get it until after Christmas.)
Finally, for a watch that's super fancy looking yet frankly useless to the vast majority of people in 2014 there's the pocket watch. These are terrific for people who do Steampunk cosplay or who enjoy being extremely retro. For most people, though, if they want to pull something out of their pocket to find out what time it is, they pull out their cell phone. And they definitely don't want a pocket watch in their pocket because it might scratch the screen. In fact, apparently most people my age don't wear watches at ALL (I find looking at my wrist more convenient than pulling something out of my pocket, but I also get a newspaper delivered to my house every day, even though I'm only 41.) Anyway, the other thing about a pocket watch is that if you actually do use it regularly, it will die quickly because pocket lint gets in there.
Heated Travel Mugs
Who doesn't need a travel mug? (A few years ago, during the after-Christmas sales, I discovered a pile of gift-boxed travel mugs at OfficeMax that had been marked down to $3/mug or something like that. I bought six. I'm down to one. I am pretty sure I lose more travel mugs than gloves.) For the passive-aggressive bonus, gift a heated travel mug that will plug into the car outlet and keep the drink warm except that this one, according to reviews, will break almost immediately.
External Phone Charger
If you have a smartphone, you could totally use a compact external rechargeable battery. Unlike most of the products I suggest, I have actually owned this one (not a gift -- I bought it for myself) and can personally vouch for it being a complete piece of crap. (It looks like you can spend $7 more and get a very similar item that usually works instead of one that usually doesn't work -- so if you're giving to multiple people, you could give nearly identical items to the people you DO like, which seems like a passive-aggressive grand slam.)
People who dislike gift cards describe them as being like given an errand. So make sure, if you give someone a gift card, to pick something that really is an errand. For example, you could give someone a gift card for an oil change. Or a gift card for a set of car washes (you'll need to buy that one locally to you). A gift card for a dental cleaning is probably more than you want to spend, but it definitely says, "I care!" while at the same time offering up a genuinely unpleasant experience. Office supplies are one of those things everyone needs (where else would you go to get printer paper, toner, and ink?) but are always annoying to go get. (At least around here. They're perpetually understaffed and so the wait for service is always too long.) Speaking of long lines, if the person's crafty you could give them a gift card for Jo-Ann Fabric. (I'll go there for other craft supplies if I'm near one and I need something, but I refuse to shop there for fabric; life is too short to stand in that cutting line. Ever.)
Passive-Aggressive Gift Giving Guides from Previous Years:
2010: Beyond Fruitcake: Gifts for People You Hate
2011: Gifts that say, "I had to get you a gift. So look, a gift!"
2012: Holiday shopping for people you hate
2013: Gift Shopping for People You Hate: the Passive-Aggressive Shopping Guide
Also, if you're amused by my writing, check out my science blogging at Bitter Empire: http://bitterempire.com/author/naomi-kr
My (kind of low-volume) Twitter feed: @naomikritzer
Or my fiction that's free online:
Bits (possibly NSFW)
The Good Son
Honest Man (downloadable audio)
St. Ailbe's Hall
And if you like that you could consider buying:
Comrade Grandmother and Other Stories (short story collection)
Gift of the Winter King and Other Stories (short story collection)
My novels (there are five of them)