I'd like to say that I'm an easy person to shop for, but I'm not. It's not that I'm picky, or that I have everything I could possibly want—it's that I rarely get around to making a list, so nobody has much of an idea what to get me. Besides, in my adult life I've discovered that (at least where family is concerned), I usually appreciate a gift that comes in an envelope (read: check or gift certificate) more than one in a box (read: another flannel nightgown). But, sometimes, when you're doing your more obligatory gift shopping (for your mail person, for instance, or your intern or next-door neighbor—those other people who are historically difficult to shop for) it would be inappropriate to give somebody a check, and a gift certificate seems either too impersonal or too transparent (enabling the recipient to know exactly how much you think your relationship is worth), so you're stuck having to buy... something. But how do you figure out the right gift in these situations? When you're buying somebody a token rather than making a sweeping gesture, what should you do?
Well for starters, something material is always better than something intangible. Don't dedicate a star to your hairdresser or plant a tree in Brazil for your handyman and then give them the certificate showing you did so. For better or for worse, people are a little selfish this time of year and they want more than a piece of paper (unless that piece of paper is the aforementioned check) to take home with them.
Something, perhaps, like baked goods. Unless you know your recipient to be on a very strict diet, or to have an allergy to chocolate/nuts/wheat flour/sprinkles, you really can't go wrong with a big ol' tin of homemade treats. Sure, the cookies you get in the blue container at CVS are fine, but something about fresh, made with love and trans fats cookies will be sure to light up just about anyone's holiday.
Speaking of "lights" and "holidays," it should go without saying that you might want to consider exactly which winter holiday your gift recipient will be celebrating. Sure, Americans have largely removed the "Christ" from "Christmas," but there are Jews better at practicing their religion than I who might not appreciate that their otherwise inoffensive tin of gingerbread men and chocolate chip cookies came with a card depicting Mary and Joseph and the little baby Jesus. I'm just saying...
That being said, don't go out of your way to get a religiously- or culturally-appropriate gift for everyone on your shopping list. Try shopping for the season, if nothing else: who doesn't love a nice scarf or a pair of warm gloves? (Or, if you're shipping the gift to New Zealand, a new beach towel...)
Holidays are generally a time of over-indulgence when it comes to booze (all that family time!), so gifts of alcohol can really go either way when you're buying your more casual gifts: either you'll be the recipient's new best friend for enabling him to make it through another dinner with his mother-in-law, or you'll be the recipient's wife's new worst enemy for making him pull down his pants and moon his mother-in-law. In general, booze is fine for the casual acquaintance so long as he's not so casual that you're unsure of his drunken behavior or previous AA meeting attendance.
Finally, don't feel compelled to out-do others when giving this sort of gift. Sure, you see your mail carrier every day, but that doesn't mean you're as friendly with him as your next-door neighbor, who knows him well enough to ask about his kids/dog/wife/secret lover. So if your neighbor gets him a giant gift basket from Harry and David and you just give him a plate with a dozen cookies on it, you're not being cheap—you're giving what you think is appropriate for the situation. Holiday gift giving in situations like these isn't about one-upsmanship and it's not about breaking the bank: it's just an opportunity to say thanks, and you're saying it your way.
Image Credit: Flickr user Ja-nelle.



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