We’re told the holiday season is all cozy sweaters and sugar cookies, but let’s be real: The emphasis on gift-giving, party-going, and family-gathering always ends up being at least a little bit stressful. The reality is that if you don’t properly prepare and set some internal expectations, the mix of financial constraints, social anxiety, and complex dynamics can leave you with more dread than joy.

So, with input from our friends and colleagues, we’re here to help you think through a few common conundrums you might encounter in the weeks to come. Below, you’ll find nine holiday etiquette questions and advice from our peers on how to handle them.

“Gag gifts or novelty gifts are fun if you know that the group is on your wavelength; otherwise, someone could be stuck with something that will basically go in the trash. It’s like giving a specific lipstick color that doesn’t suit everyone; it’s really nice if it ends up with the right person, but otherwise, it’s entirely useless. You want to try and ensure that everyone who participates gets out what they put in, and that goes beyond spending an equal amount of money.” —Hanna

“I don’t think it needs to be useful at all; just make sure it serves some purpose in that it brings laughs or good energy to the party. One year, my friend brought a Grinch mask, and it stole the show. That being said, I never used it again, which is pretty wasteful…” —Anna

“In my opinion, the best gifts are gifts that the recipient wouldn’t buy for themselves, so I don’t think a gift has to be obviously ‘useful.’ Of course, for white elephants, you don’t know who will end up with your gift, but I still abide by the same principle and go for things that most people will enjoy, whether functional or not.” —Cindy

“It depends on the group you’re doing the gift exchange with. For a group of friends I know well, it can be fun to come up with something that may not be necessarily practical but is still useful in terms of its entertainment value. For a group of people I don’t know as well, I tend to gravitate toward more generic gifts, since I don’t know everyone’s preferences.” —Maggie

“I usually go to a white elephant party with the goal of making people laugh at my gift of choice. For this specific type of exchange, I think the experience is more important than the quality of the gift. Even if I leave with an item I’ll never use, the memories I had with my friends or family are worth it.” —Alana

“Not if done correctly: If regifting, the item should be truly unused, still packaged, and generic enough that it won’t raise eyebrows. We should be aiming to eliminate waste, so if you got a candle that gives you a headache, you can certainly give that to a friend who would appreciate it rather than throwing it away. That said, you want to make sure the old gifter and new giftee do not cross paths.” —Hanna

“It depends on the gift and the situation. If it’s something like a gift for the host, I think it’s totally fine to regift! If it’s a personal gift—rude.” —Anna

“As long as none of the involved parties (the recipient and the original gifter) know you’re regifting, and it’s something the new recipient would genuinely enjoy, it’s totally fine. It’s also objectively more sustainable than keeping something you won’t use! In my opinion, you cross into rude territory if you’re only regifting to get an item off your own hands, rather than passing it on to someone who will genuinely appreciate it.” —Cindy

“I really try to be conscious about not wasting things, so I think it is fine to regift items to someone else if it’s unused, unopened, and you truly believe they would get more use out of it. However, I do think it’s best not to regift to someone in the same social circle!” —Maggie

“It’s fine if (a) the person will never find out you’ve regifted their gift and (b) you know you will never use the gift, and someone else would love it.” —Alana

“In most situations, gifting a colleague can be considered appropriate. As M.M.’s Director of People, I do have a lot of opinions on this, though! The most appropriate gifting relationships look like the following: manager gifting direct reports, office BFFs gifting each other, and individuals gifting colleagues who have put a lot of effort into supporting their work or experience (office manager, etc.).

My HR brain also thinks of the following rules:

• Keep gifts within reason, i.e. a small gesture rather than a flashy overture.
• Gift equally. If gifting to one direct report, gift to all of them.
• Exercise caution when gifting to people above you in your organization’s hierarchy to ensure you are not attempting to curry favor or sway a decision.
• Keep gifts work-appropriate.
• Don’t forget to tip office building staff!”

—Hanna

“If you’re friends outside of work, they’ve given you a gift in the past, or you’re doing something for your whole team, it’s appropriate. Just keep it small, so it’s a nice gesture and doesn’t make them feel uncomfortable if they didn’t get anything for you.” —Anna

“If you’re actually friends with a colleague, it’s appropriate. While I definitely don’t believe it’s a requirement, I also think it’s okay (and often appreciated!) when a manager gives their report something small.” —Cindy

“I typically only give gifts to colleagues if they are someone I have become friends with outside of work. In the past, my peers and I have also gotten together to gift something small to our manager as a way to say thank you.” —Maggie

“If you’re close with your colleague outside of work, then it’s appropriate. I think getting a small, inexpensive item such as candy for all your colleagues to share is also an appropriate way to celebrate the holidays at work.” —Alana

“No advice here—we usually just assume ¯\_(ツ)_/¯.” —Hanna

“I’m an only child, but my friends and I often always do white elephant or secret Santa exchanges, in which case we’ll set a price limit! We tend to keep it low, because at the end of the day, it’s about being together.” —Anna

“I’d just ask! Everyone’s finances are different, and for some people, the holidays can be a tight time. What’s important is that you want to give people something they’ll enjoy. So if you and your siblings have a relationship where you’re giving each other gifts, I think it’s fine to ask and be transparent if you have budget concerns.” —Cindy

“My siblings and I don’t typically have a set budget, but we all try to keep the gifts at a reasonable price we think each person can afford. Because there are three of us, two siblings will typically go in on gifts to give to the third. This way, we can share the cost in whatever way we feel is appropriate. We are close enough with each other that if we felt something was a little out of our price range, we’ll bring it up and come up with another option.” —Maggie

“My sister and I have never established a budget for gifts, but we also have never been overtly unequal in our gift value. I think over the years we’ve learned how the other person gifts. When I shop for her, I don’t think about a number; I just try to think of one good quality item she would want.” —Alana

“I’m not well suited to answer this one. I fight my uncles….” —Hanna

“If anything comes up, I do my best to try to change the subject.” —Anna

“Eek. I don’t think there’s a ‘rule’ for this; everyone’s families are so different and dynamics can be very complicated. But in general, I think it’s important to set your own boundaries and respect each others’, as well. If you don’t want to engage in a conversation further, be clear about that boundary. If others want to continue discussing, it’s okay to remove yourself from the conversation. If someone else sets a boundary, respect it and encourage the rest of your family to respect it, too.” —Cindy

“My family is pretty close, but we definitely don’t see eye to eye on everything. In most cases, we can discuss sensitive topics while being respectful of one another, but I would say I have learned which topics to avoid with which family members, because it never results in a productive discussion. In those cases, I typically offer pretty vague answers and then redirect the conversation to something else.” —Maggie

“I usually focus on asking questions I know I’ll be comfortable answering. Knowing your audience is really important in navigating dinner conversations. If it’s just my immediate family, I know where everyone stands politically, and I also know what may be too personal for some to answer. Ultimately, when in doubt, I just don’t bring it up.” —Alana