'I smiled and chuckled and held back my tears': Entitled boss’s Secret Santa 'gift' leads employee to quit and HR to step in

Author image for Isabella Penn
Isabella Penn
Dec 25, 2024 10:00 AM EST

Work Secret Santa exchanges are supposed to be a fun and lighthearted way to spread some holiday cheer among coworkers who you mostly know through passive-aggressive email chains and awkward breakroom small talk. But somewhere between the budget limits, unspoken expectations, and trying to avoid the holiday burnout, things can go south fast.

The reality is that Secret Santa is like workplace roulette. You might get paired with the coworker who genuinely knows you and nails the gift, or you might end up with someone who thinks a half-empty Yankee Candle and a Post-It note saying "Enjoy!" is appropriate. But the most dangerous scenario is drawing your boss. Suddenly, what should've been a $20 token of goodwill feels like a make-or-break moment in your professional life.

That's exactly what happened in this story. One employee went out of their way to pick a thoughtful gift for their boss… only to get completely blindsided by what they received in return.

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  • 01
    Cheezburger Image 10446666752
    via Unsplash (Getty Images)

    This image is for illustration only, and the subjects are models; the image does not depict the actual subjects of the story.

  • For this Redditor, drawing their boss’s name felt like a chance to make a good impression. They went above and beyond with the gift, even packaging it in a beautifully decorated box filled with hand-folded origami stars and a garland for her monitor. Thoughtful, creative, and within budget—basically the Secret Santa trifecta.

    But when it was time for the boss to return the favor, things got weird. Instead of a gift, the Redditor received a card that said, “It’s been a pleasure working with you this year, now go clean out the store room.” Hilarious, right? (it wasn’t). Keep reading to see what the boss's actual gift was, how HR got involved, and why it caused this employee to quit.

  • 02
    r/ r/coworkerstories • 9 hr. RadioSupply Another Worst Secret Santa story
    via u/RadioSupply
  • 03
    It just so happened that I drew my boss, and my boss drew me. There was a $20 limit, so I decided to get her favourite brand and scent of fragrance oil she used in her office diffuser. The oil cost $15, so I put it in a cute box full of tiny origami stars I'd made and strung into a
    via u/RadioSupply
  • 04
    garland for the back of her monitor (she loved decorating her office.) I received a card, and inside was a note that said, "It's been a pleasure working with you this year, now go clean out the store room." I smiled and pretended
    via u/RadioSupply
  • 05
    there was a big joke inside, but my boss laughing and smiling - - took my card and read it aloud to everyone. A few people laughed, then the HR lady (her best friend) asked if there was a gift. My boss said
    via u/RadioSupply
  • 06
    she'd "take care of me" later. The "taking care of me" was letting her drive me through the Starbucks drive thru and having a coffee on her company credit card while she spent the 10- minute drive not-apologizing and raving about her very funny joke.
    via u/RadioSupply
  • 07
    I smiled and chuckled and sipped my Pike Place and held back tears. $15 isn't much, but every dollar counts and I had decided to short my own mother a stocking stuffer because of the secret Santa. I found a new job a few months later and spent the last few months there avoiding my boss.
    via u/RadioSupply
  • 08
    The kicker: HR asked if I received a present from my boss. I told the truth and said she bought me a coffee on the company card. She said she was sorry and would look into it. Crickets. Meanwhile, my boss's monitor looked adorable, her office smelled fragrant, and I hope she told her story of how she f ed me over the holidays and got at least a small side-eye.
    via u/RadioSupply
  • 09
    Planmaster3000 • 9h ago I think it's telling that HR followed up and don't assume it didn't lead to - anything these things go in the personnel file and can definitely influence promotions (and terminations).
    via u/Planmaster3000
  • 10
    Also, f*** her and the horse she rode in on! I'm sure she didn't win any points with the rest of the team. And as a recently retired senior manager, you never want to lose points with your team - they either make you look good or like an incompetent From • this anecdote alone, we can all see which your boss is.
    via u/Planmaster3000
  • 11
    frankydie69 • 10h ago Used to be a receptionist at a medical office. One of the doctors got me for secret Santa. I was stoked cuz it was a doctor and we've all seen doctors give good gifts.
    via u/frankydie69
  • 12
    Well this doctor decided two big Reese's candy's and a hersheys kisses bag was good enough for the secret. Santa gift.
    via u/frankydie69
  • 13
    Meeber 8h ago ⚫ This is why I'm anti-secret Santa at the office. And gifting up. There's always some ppl that just do not give af, and others that go overboard. It just creates awkwardness and hurt feelings.
    via u/cMeeber
  • 14
    Gracie Thunders • 9h ago Slip a little anchovy oil into her diffuser when she isn't looking
    via u/GracieThunders
  • 15
    Impossible_Balance 11 • 8h ago Gifts should only flow top-down, never bottom-up. No employee should ever have to buy a gift for their boss in any shape or form. "Haves" should give to the "have- nots."
    via u/Impossible_Balance11
  • 16
    No_Stress_8938 • 9h ago • It looks like boss lady got a bit of a high off acting like "a boss". Even on a bad day, I would never tell my subordinates to "go clean the closet". Even as a joke.
    via u/No_Stress_8938
  • 17
    . hrroyalgeekness • 6h ago I don't understand joining a secret Santa just to give gifts. The whole point is to find sweet things for the person for under a certain price point. This year, my person's favorite thing was a screaming goat I found on clearance that I tucked in with a food related treat.
    via u/hrroyalgeekness
  • 18
    iroze 7h ago • Our big boss thought it was fine to pack a tin of Vienna sausages and a bottle of Pepto Bismol as someone's Secret Santa gift. Literally no one laughed except him. Awkward af.
    via u/iroze
  • 19
    rchart10107h ago • I've said it before and will say it again. Offices should just stop doing secret Santa period. It's not worth it for the 10% of the time it ends poorly. And no matter how optional you say it is people. always feel forced to participate even if they don't have the money. It's particularly that to you. your boss did
    via u/rchart10107h
  • 20
    -NigheanDonn • 6h ago Oh man I would have been tempted to get the most ridiculous over-the-top drink from Starbucks, like extra shots, flavors, toppings etc. Even if it was undrinkable but I would ... probably have cried into my black coffee too. I'm sorry she did that to you, I hope your new boss. treats you better.
    via u/-NigheanDonn
  • 21
    lamNotTheMama • 6h ago • I would throw in a touch of petty revenge after the crickets from HR - remove all of your gift from her office, either put it in your own or throw it in the dumpster (where boss can't find it).
    via u/lamNotTheMama

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christmas boss gifts employee hr job work coworkers Secret Santa quit Party colleague Horrible Bosses Reddit holidays
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