Over the years I've participated in a number of different types of Secret Santa exchanges, from in person exchanges with friends and exchanges within a student group (such as CKI) with strict or not so strict financial limits, to larger exchanges across the country with Goldfishlegs.ca (a contesting community), or worldwide with BoardGameGeek or RedditGifts. Each of these exchanges have been met with varying degrees of success and this has a lot to do with the community that has sprouted up about the exchanges. Currently I mainly participate in the BoardGameGeek and RedditGifts ones (yes, I participate in RedditGifts yearround, but the biggest emphasis is on their awesome Secret Santa which is by far the largest and often times the most fun -- but then again I also rather love their Trick or Treat and Arbitrary Day exchanges plus a number of their themed exchanges too). I find that it's important to have some commonalities between one's self and the other participants in an exchange for it to be enjoyable (I don't exactly fit the average demographic from GoldFishLegs.ca though I do still love that contesting community. I didn't find their secret santa as enjoyable as a result, though that impression might change if my personal life situation changes). That said too much familiarity or similarity is not always ideal either -- it's kind of nice to find the unexpected (and in the case of international exchanges, things you cannot find locally) in a gift.
But what makes a good gift? I find it really varies on the person and this is why this is often a difficult question. Sometimes it's a case of finding something someone has longed for, while at other times it's simply finding something that they didn't even know existed or that they didn't know that they wanted. Sometimes the search is easy and quick whereas at other times it's complex and filled with potholes. Finding gifts that fit into one's budget etc. is another constraint too... but I really do enjoy the process in general.
And so since today marks the first day of signups for the RedditGifts Secret Santa, I encourage you all to take part if so inclined... or if not, to be a bit more aware of the joys and tribulations of such gift exchanges.