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No matter how well you know (or think you know) the recipient, a piece of art is for most people an utterly personal choice – a badge by which people express themselves. And considering how expensive it can be, it's a dicey idea as a stocking stuffer (most galleries don't have a 30-day return policy, after all). Gift giving at the holidays should be about finding special, thoughtful items that the giftee wouldn't otherwise buy for himself. Art just happens to be a perfect example of something people like, even love, to buy expressly for themselves. So why get in the way? A real collector will take it too seriously to appreciate your easygoing effort, and even a casual art lover is likely to have discerning taste about what hangs in his home. Both will feel obligated to prominently display your present (at least when you're around), which is likely to leave a bad taste.