The idea of Secret Santa has been around for as long as there have been offices and over-eager co-workers. It adds a little fun and mystery to workaday proceedings, but it can also add stress to an already stressful time of year: Now I have to get something for Gary? Wait, who is Gary?

As a Secret Santa participant — this is very important — you want to establish a reputation for yourself as a good giver. That way, in future years, whoever gets you will have to bring their game and come up with something better than $20 worth of Christmas-themed band-aids, lest they be publicly shamed. It’s generosity borne out of selfishness! Here are four ways to make sure that you’re the best-kept (as in, employed!) secret.

Respect the price limit… to a point. Go slightly over, thinking of it as an investment for later. Don’t, of course, blow everyone out of the water by getting your giftee an iPad. Let’s pin the overspending number at 20%; so, if the limit is $20, spend an extra four bucks and explain that while you did go a little over, this thing was just so perfect for Gary that you couldn’t resist. Woah, look at Mr./Ms. Thoughtful here! He/She just can’t help it!

Listen to hints, and be careful what hints of your own you put out there. Be on alert for your person expressing an interest in something, anything, and if it fits your budget, get a slightly upgraded version of whatever that thing is. Be sure to mention that you overheard them saying they liked x, so you went out and got y. Thoughtful and creative! Remember, though: If you casually mention how you enjoy the odd Frappachino during the Secret Santa danger zone (right after the draw or right before the gift exchange), you’re getting a Starbucks gift card. Better to just casually mention you like diamonds.

Subtly remind people what a good Secret Santa you are. (Note: This only works if you’ve already laid some groundwork in years past.) As the draw looms close, find a time when all or most of the parties are in the same place (meeting, carpool, court date). Follow up with your previous recipient; asking how they enjoyed that awesome back massager you gifted last year. Look at you, so thoughtful you’re even checking in a year later! That’s good Secret Santa customer service right there.

White Elephant/Yankee Swaps game theory: If your workplace participates in the so-called White Elephant or Yankee Swap variant of Secret Santa (sometimes also hilariously/disturbingly referred to as “Dirty Santa”), this means two things: 1) Your office clearly does not care about productivity, as these things always go on for hours; and 2) You are in for a treat. While the chances of you getting something are low, someone always takes things way too personally and gets furious. It’s delightful.

One way to game the White Elephant/Yankee Swap system is to bring something totally worthless, thereby guaranteeing you come out on top. The downside is that this will make you an outcast, plus there’s a chance you’ll end up with that thing anyway. Better to trick everyone into thinking that you’re in possession of a fantastic gift despite it being something you don’t want, and vice-versa. Really talk up that stinky scented candle as if it’s the Hope diamond, loudly proclaiming that you “hope” (eh, eh?) nobody steals it. Once you do get your hands on something good, act as if it’s totally worthless to you. Or hide it behind some wrapping paper.

Got any Secret Santa strategies or Yankee Swap horror stories? Let me hear them in the comments!


Paul BeerPaul Beer is a Toronto writer, actor and comedian. You can follow him on Twitter @pauldanielbeer.