 Should you get them a gift? According to experts. Will you eat or drink for free at their party? Get them a small gift. Were you asked to bring something specific? No gift necessary. Are they your boss? Don't get them a gift. How about coworkers? Only if you utilize the Secret Santa loophole. Otherwise, don't make it weird. Service workers you see regularly? Yes, but please nothing homemade. Family you're spending the holidays with? Unless you Secret Santa it, you gotta get them gifts. Kids of people you're close to, get them a gift. But if there's more than two siblings, a group gift will work just fine.