So, you want to give a gift, or you have to give a gift. Either or both.
Do you pick the gift that you know the person wants? Do you genuinely try to satisfy their desire and give them the thing that they most want, cross-referenced with the list of your realistic capabilities in that regard?
And if you want to give them the gift that they most want, do you make things more efficient by asking them what that thing is? Or, is what they most want to be surprised by someone who knows what they want without them having to tell? Or or, is what they most-most want to be surprised by someone with the intelligence to ask them, given how impossible the conundrum is otherwise, what it is they actually want, and who is helpful enough to just ask them beforehand, because that shows what true friends you are that you're not bound by ridiculous and hyper-modernized notions that no longer apply in an age when everyone you know that well already has the essentials met and is the only one who knows how to pick vinyl that will fit perfectly with their record collection, and would be irritated at having to return or destroy something that you, in your best heart of hearts, picked incorrectly due to your inability to understand the exact right kind of woodworking equipment and/or silent film collection that will match with what they already have?
What if they're clever enough to drop hints about their philosophical feelings on the matter beforehand, so that you don't have to ask? What if they're not that clever, but think they are, or are that clever, but you're not, and neither one knows what the other one knows about what the first one knows about what s/he wants to receive?
To preserve the surprise, do you ask the future recipient to give you a list of things Recipient likes, or just a generalized range of things that Recipient likes, and choose from among them, so that there's at least some element of surprise, if not totally? And what if, by supplying you that list, they were only providing you with a more complex test? I.e., "She knows what I really want"?
What if they don't want anything, and they're going through with it only because they think that allowing you to give them something will make you feel old-fashioned? What if they're groaning about how much you spent, and where they're going to store it, and how they're going to remember to not give it back to you next year, but to someone else, instead? What if you've seen the inside of their back closet, where they store all the gifts from prior years with labels that remind them who gave them what, and who they should re-gift the gifts to? Should you still give them one?
What if Recipient is facing the same conundrum, but knows that she can never tell you this, because you might only be projecting your own struggles with the same conundrum in order to relieve her from the pressure of the conundrum with regards to you? Do you know each other that well? And, if you blow everything off to prove that love matters the most, and it turns out one of you faked the other out through no fault of your own, will it destroy your relationship, or perfect it?
And what about quality? What defines true selflessness? Do you give them the gift that you know they want, or do you give them the best gift? Do you give them a collection of fine cigars, or do you give them a free membership to the local quit-smoking club? Or a box of nicotine patches, as though those help with cigars? Fine, pretend it's cigarettes, then--do you give them the smokes they want, or the "best" thing for them?
If you give them what they want, does it prove that you're sweet and good and non-judgmental? Or does it prove you're enabling them? Ten years later, when they quit smoking, will they remember how you gave them the cigarettes they wanted, and think of you as part of "the bad phase" of their life? Or will they think, "Gosh, she really respected me, even when I was a f- up"?
If you give them what you know they really want, are you lazy? Should you have made something homemade, instead? Or, if you make them some homemade crap that nobody wants, does it show that you're too cheap and arrogant to give the gift they really want, or does it just make them feel terrible inside because you're so genuine and all they did was get you another bottle of expensive scotch in an even-more-expensive laminated carton that comes pre-printed with pictures of embossed griffons having sex with a variety of types of oceanic waves?
And can you trust them if you ask them beforehand, and they promise you it's fine to give ________, and only ________, and nothing but ________, because ________ is what they've wanted ever since last year, when what they also wanted was ________? No, you can't trust them. We can't none of us trust another, because the higher the stakes and the more genuine the relationship, the more rides on the decision, and the more motivation to give the greatest gift of all: lying to them that it doesn't matter, or, telling them something little and cheap so that they'll be tricked into thinking that it did matter, but feeling better about it because they've satisfied your explicit requirement. They'll suspect you of doing that, and you'll suspect them of the same, but then if you both back out and get the other nothing, you're left sweating until the first instant of Boxing Day, wondering if you're the one who's about to get suddenly gifted, and become the secret scrooge whom everybody loudly praises for practicality but privately talks about over the pillow after the party's over, should you feel bad, helpless, or righteous?
What if you want to show everyone how painful it is, so you give them the best gift you can honestly think of, a nice meal with everyone who showed and lots of genuine love, but not a new electric razor or European waxing kit or E350? If you ask everyone to help make the fudge or sing along, are you giving them real memories, or are you just a cheap sonofa? If that's what you actually think is a gift, are you still a vile bastard? And if they thank you from the bottoms of their hearts and then give tangible gifts at a ceremony separate from you next year, does it make you feel vindicated, bad, or piteous? If you give in, and just buy the damn E350 in iridium silver metallic with the cold weather package, and give everyone a gift basket with their very own hand-imported Peruvian fudge and new smartphone, does that finally satisfy things, or does it make you the pompous clown who's trying to buy happiness and doesn't really understand the holidays?
And how in-between is "in-between"? You can't just get Cracker Jax, and maybe the XJ series is pushing it, so, err, is a space heater so practical that it conceals your lack of imagination? If you give everyone reasonably priced self-inclining massage chairs, and then your best friend just reads the room a poem she took a week off from work to write, and everyone congratulates her and wipes away tears, do you wish you could go back in time, forsake the couches, and write your own poem? Or do you pity your friend for not realizing everyone's going to be hating her in secret as they vibrate their back muscles in the chairs you had delivered to their homes before the party, getting electronically massaged while they laugh about how naive and cheap Becky is for coming up with a poem she probably plagiarized from Dickinson anyway?
Let's make a deal. I'll buy you a vegetarian cookbook, you buy me a Bible, and we both promise not to argue for one year. No, even better--get me a carton of Marlboros and I'll print you up a coupon to have your leaves raked out of your yard the next fall. Then you'll laugh, and make me re-print it along with a disclaimer of any rescheduling in the event it starts to rain on the day you ordered the raking, and another one for no dirty looks at the house while work is being performed.