Playing the Game
Write the names of everyone participating on a piece of paper. If the group is larger and people do not know each other that well, it is a good idea to get people to write their names and some distinguishing features/interests, such as "male astronomy buff, 65" or "female triathlete devotee, 34". In more intimate group environments, only the name of the person is necessary.
Cut out and toss the names into a hat. The next step is to prepare the names for a drawing. Cut each name out and then fold it in half once or twice to prevent people from reading it without unfolding it. Then place all the folded names into a bowl or hat and mix them around a bit so that the names are shuffled.
Set a price limit. This can be done in discussion with the whole group or just by those who are organizing the event. The price limit is set so that some people don't try to be cheap and get away with purchasing a gift for only a few dollars, while others try to overachieve and purchase very expensive gifts. Select a price limit in the ‘happy medium’ range that you know everyone in the group can afford. It’s better to be safe than sorry and choose a lower price range than to choose something too high that some people don’t have enough money for.
Draw names. Work around the group, giving everyone the opportunity to draw a single name randomly out of the hat. Keep the names folded and hidden until everyone has drawn. At this point each person can look at their name, as long as they are careful not to say who they have or to show anyone else their slip of paper. If someone draws their own name, have them redraw.
Set a gift-giving date. The next step is for everyone to go out and purchase a gift (within the price range) for the person whose name they drew from the hat. Typically, there is a second meeting time at which all the secret Santa players exchange gifts and reveal whose name they had the whole time. Check with the members of the group and select a date and time several days in advance at which everyone can meet to exchange their gifts.
Purchase a gift. With your person in mind, go out and choose the perfect gift for them. Try to make it personal, and avoid choosing a generic gift like a coffee mug or a bag of candy. Be intentional about matching the price limit though or you may make your gift recipient or others uncomfortable with how cheap or how expensive you were.
Exchange gifts. When everyone in the group has purchased their gifts and met up together, you can begin the gift exchange. Wait until everyone is present and continue keeping your gift recipient a secret until everyone is given a ‘go’ to start exchanging gifts. At that point, find the person to match the name you drew, and reveal your gift! Don’t forget you’ll be receiving a gift as well, so remain gracious and polite as you accept your present (even if you really don’t like what you got).
Choosing the Right Gift
Keep it appropriate. Gag gifts are fun sometimes, but in general you should always choose gifts that would not be perceived as inappropriate for a group setting.
Avoid alcohol. Unless your secret santa is happening at a wine tasting party, you shouldn’t assume that your gift recipient will appreciate a bottle of alcohol as much as you or someone else might. Especially at office parties, giving alcohol could create an awkward exchange if your recipient doesn’t like drinking or is recently sober. If your recipient is an alcohol enthusiast, try choosing a related gift rather than alcohol itself (like wine charms or a beer koozie).
Buy something practical. If you are not quite sure what to get your person, play it safe and choose something that is practical and useful. That way, even if it isn’t something that they might have wanted, they will still have a use for it. Consider holiday ornaments, kitchen necessities, or a good book in a genre they’re interested in.
Get something specific. If you can, do a bit of research on your gift recipient in order to choose a gift that is truly tailored to them. Ask around, look at their work or social media profiles, or discreetly do a bit of questioning with them. They’ll appreciate the time and effort you put into choosing a gift that is special and geared towards them.
Consider making a gift. If you’re the creative type, a homemade gift done in good taste will seem personal and meaningful. Consider your recipient’s interests when making a gift for them, rather than just throwing together a bunch of scraps and appearing cheap. There is a big difference between making something creative and worthwhile, and making something cheap and lazy because you forgot to/didn’t buy something.
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