Funny Christmas Wishes for Your Boss
Finding the perfect Christmas wish for your boss can be tricky—too formal and it's boring, too casual and it's awkward. A funny message strikes the right balance, showing appreciation while keeping things light. Here are 10 hilarious wishes that'll make your boss smile (or at least chuckle).
Wishing you a Christmas so merry, you forget to check our timesheets until January.
“May your holiday be filled with more joy than finding an extra coffee pod in the break room.
“Here's to a Christmas break long enough that you actually forget our names. We'll remind you.
“Not specific enough?
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“May your eggnog be strong and your out-of-office reply be longer than our project deadlines.
“Hope Santa brings you the one thing you really want: employees who refill the printer paper.
“Wishing you a Christmas so relaxing, you consider making every day 'Casual Friday' in the new year.
“May your holiday calories not count, just like those 'quick' 5 PM meetings that aren't quick.
“Here's to a New Year's resolution to finally fix the thermostat in the office. We believe in you.
“Wishing you a Christmas where the only 'urgent' email you get is about cookie recipes.
“Common Questions
Q.Is it appropriate to send a funny Christmas card to my boss?
Yes, if you have a good rapport! Funny cards work best in casual workplaces or with bosses who appreciate humor. Avoid jokes about pay, promotions, or serious office issues—keep it light and festive.
Q.Should I handwrite the card or send it digitally?
Handwritten cards feel more personal for office settings. If you're remote or your boss prefers digital, an e-card works too. Just make sure the humor translates well without your tone of voice.
Q.What if my boss doesn't celebrate Christmas?
Stick with generic 'Happy Holidays' or 'Season's Greetings' wishes instead. You can still use funny tones—just avoid Christmas-specific references like Santa or reindeer to be inclusive.