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

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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Author image for Isabella Penn Isabella Penn
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