Secret Santa can be fun, but without some simple guidelines, it can easily devolve into headaches and awkwardness. The secret is to keep it straightforward. Here’s your stress-free guide to a Secret Santa exchange people will enjoy.
Decide on a budget and set limits early

Financial issues are the number one source of conflict in Secret Santas. Set one maximum price that everyone can stick to, and send the information out to everyone early. Setting the budget in advance keeps expectations the same for everyone and prevents awkward moments where someone overspends.
Choose a tool for assigning gifts

Selecting names in person or by hand is fiddly, and people often forget to swap names later or regret their picks and want to change. Secret Santa apps and websites pick names automatically and anonymously. Secret Santa gift exchanges that use wish lists tend to have a lot fewer headaches, since people don’t have to resort to guesswork when buying gifts.
Communicate about gift parameters

Gift restrictions are a regular source of unhappiness, so make sure everyone is on the same page from the start. For example, do you want gag gifts to be allowed? Are you picking a theme? Do you want useful gifts, gag gifts, or both? Is alcohol or gift certificate allowed?
Setting gift expectations in advance and making it clear that everyone has the same restrictions will reduce disappointment and prevent arguments later.
Create deadlines and enforce them

Select one deadline for when gifts need to be purchased, and one deadline for when they need to be delivered. Deadlines reduce the likelihood that people will put gift selection off until the last minute and engage in that spiral of online shopping despair that only results in expensive junk and buyer’s remorse. Setting and sticking to deadlines makes gift exchanges smooth and easy.
Gift should be thoughtful, not expensive

Set the tone by reminding everyone that this is an exercise in consideration, not generosity. A gift of modest value that shows the giver paid attention, i.e., a favorite candy, a hobby-related item, a personalized trinket, etc., is almost always more meaningful than an expensive but impersonal “grab-bag” gift.
Decide where and when people will exchange gifts

Will the Secret Santa be in-person or remote? If you’re all in the same place, a fun way to do it is to have each person draw their name and open their gift right then.
For remote groups, each person mails their gift in advance and opens it during a video chat or each person drops their gift in the mail right before the event. Decide early so people have plenty of time to make sure gifts can arrive in time and figure out packaging.
Have a plan for no-shows and dropouts

Life happens. Someone may drop off the radar at the last minute due to a conflict, a family emergency, an illness, or sheer forgetfulness. Plan for a no-show by having one gift in reserve or set aside a fund to purchase an impromptu gift. This keeps things from getting awkward.
Make the gift exchange fun

Gift exchanges can be more enjoyable when there is a small game element or icebreaker involved, like asking everyone to guess who gave them their gift or making everyone share a holiday memory. Try to keep it optional, so people who don’t want to participate in the fun gamey part don’t feel put on the spot.
Rotate the organizer position

Managing a Secret Santa every year can be stressful. But Secret Santa need not fall on the same group every year, nor does the same person need to organize the gift exchange every year. This spreads the responsibility and also allows for new ideas to be included.
Be accepting of swaps or returns

Gifts don’t always match, and sometimes people will need to swap their gifts or return them for something else. Approach this with an understanding attitude rather than making people feel embarrassed, and resolve the issue as easily as possible. A gift exchange is supposed to be fun, not stressful or hurtful.
Keep it simple

Avoid the temptation to add multiple gift restrictions, themes, “maximum utility scores” or anything else that will make participants feel extra pressure or anxious. A simple Secret Santa with few restrictions will run the smoothest.
Remember the true spirit of Secret Santa

The last and most important tip for running Secret Santas is to remember that this activity is supposed to be enjoyable. Secret Santa is not a competition or an occasion to judge who gives the “best” gift. Just encourage everyone to say thank you and enjoy the moment. When people focus on appreciation, the experience feels warmer and more meaningful.
The following sources were consulted in the preparation of this article: