I think of gift giving as an opportunity to show someone a whole new world view. I never give anyone a gift that they would expect. If I wanted to give someone something they were expecting, I would just give them cash instead and give them the freedom to do what they want with it.

Instead, I try to figure out what the person I’m giving the gift to would enjoy doing but doesn’t necessarily do already, and then give a gift according to that. I once gave a friend a skydiving ticket because he had never been skydiving and seemed rather against it, even though he seems to be a fan of high adrenaline activities in general. He ended up being pretty grateful.

Of course, this can backfire in some cases, but that’s a risk I’m willing to take. In one way gift giving is a proxy for how well someone really knows you.

It’s always interesting to give a gift to someone that I don’t know all that well, because on some level, I’m really just guessing about what they like and want. And that turns into a test of how good I am at guessing. As it turns out, I seem to be pretty decent at it, although there’ve been some very notable exceptions.

When it comes to receiving gifts, that’s a lot more hit and miss. People don’t seem to know what to get me most the time, which is fine, given that I don’t want for much (thankfully).

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