Most gifts that are given during the holiday season tend to fall, rather neatly, into three categories. They are: 1. Those that satisfy the requests from a pre-arranged list, 2. Those that, on account of being something a recipient has not requested, surprise, and 3. Those that have been commissioned by the giver specifically for the recipient. Each approach has its advantages, which can be weighed against another’s. The disadvantages are rather more subjective.

Ticking things from a list is an economically sound solution because the chances of failure are all but eliminated. The risk of spending real money on something that will prove to be less a gift than a burden is removed entirely, even if the request seems to everyone else ludicrous. If a man asks for a specific tie, and receives said tie only to realize some months later that mustard is not, in fact, his color, he has only himself to blame. Offloading a mustard tie is impossible, so it is best to hang it among his more sensible ones as a solemn reminder of his folly. The problem with this gifting method, however, is it carries the whiff of order fulfillment: two pairs of lisle socks; one merino knit; three linen handkerchiefs, white; one terry cloth robe… The holidays should be full of hush and wonder, not the orderliness of basic training.

Conversely, the surprise gift is the gambler’s option. The net is cast wide, and the fruits of the dredge may or may not dazzle. A watch-less fob chain? A reptilian journal? A dagger for close combat? A dusty volume of verse? A kitchen gadget? I’ve received these and countless others and can vouch, if for nothing else, for the surprise aspect of the equation. Most givers attempt to tighten their cast by trying to determine their mark’s interests. I always feel this strategy is inherently flawed though: won’t the enthusiast have a far more nuanced understanding of the desirable attributes of the item in question? I would never, for instance, seek a snuff box for a snuff box collector for fear of purchasing and gifting the wrong artifact—a blemish that the poor recipient will now have to surreptitiously shift into pride-of-place within his vitrine each time I materialize for tea. The scenario is just too fraught—too Mrs. Bucket for me.

The most confident giver might circumvent the risk of giving the wrong thing by enlisting the help of an expert. The apotheosis of this strategy is to have something made for the recipient, which is as consistently impressive as gifting things gets, but requires the cleverness of a conman to do correctly. For instance, if one wishes to have a hat made for someone special, a measurement must be taken. I accomplished just this at a dinner party once by fabricating an elaborate story about a study I had read concerning forearm length and cranial circumference. With a tape measure and notepad, my wife and I went around the table taking measurements of noggin and appendage until we arrived at my mark—my father—whose skull we made certain to measure with extra attention. Of course I then had to field questions about my findings for the remainder of the evening. He got his hat though. The wiser option is to have something made that requires no measurement, like a set of dress studs and links featuring some sentimental design or material.

My wife’s family practices a far more exciting gifting tradition—a sort of Machiavellian secret Santa. It goes like this: a group is given a modest budget to buy various gifts, some of which might be genuine, others intentionally humorous or even obviously undesirable. The gifts are anonymously wrapped. On the appointed evening, after dinner and when spirits are high, a hat is passed containing scraps of paper, numbered one through however many people are present. Number one has first whack at the pile of booty, followed by number two, three and so on. This all sounds quaint, but there is a wrinkle. Each person, after unwrapping his or her selection, has the option to keep it or swap it for something else that has already been opened. The other party has no choice but to forfeit whatever it is they decided to keep in exchange for what the stealing scoundrel is offering. My first year, not familiar with the strategy involved, I left with a car jack, a pen that functions in outer space and one of those beaded seat covers popular amongst cab drivers. We laughed and sang by the fire well past midnight. Some gifts are priceless.