10 Funniest Workplace Holiday Disasters

10 Funniest Workplace Holiday Disasters

Celebrating the holiday season at work can be full of landmines – like inappropriate gifts, disastrous decorations, and parties gone awry. I recently asked readers to tell me about their funniest workplace holiday disasters. Here are my 10 favorites.

1. Christmas tantrum

“A woman who had worked at our office for more than twenty years pouted and threw tantrums like a child if she didn’t win a door prize at the annual Christmas dinner. Every time someone else’s name was randomly drawn, she would yell, ‘FIX!”’ or ‘CHEAT!’ or something similar. And one year, she just snatched a prize she really wanted from the table and told the person who won the prize, ‘I DESERVE this,’ and walked away with it.”

2. Most likely to kiss under mistletoe

“We had a people scavenger hunt based on self-volunteered random facts. The facts were pretty innocuous, but one girl used it as an opportunity to flirt with a coworker. Her facts about herself were ‘Won Most Flirtatious in High School,’ ‘Voted as Homecoming Queen,’ and ‘Most likely to kiss under mistletoe.’”

3. Holiday skit gone wrong

“I used to work for an organization that was dysfunctional in the extreme. Each Christmas, one particular program director, who thought he was an artist, would write a skit for some staff to perform. There were choreographed dances, original songs, and worst of all, the entire skit was meant to be a parody of a particular issue that had come up in the past year. In the right hands and with enthusiastic participation, this might have worked, but believe me when I say that all of the jokes and plot points were in the worst possible taste – mocked people, brought up sore points in a condescending way, made those acting in the skit the butt of jokes about themselves, made off-color jokes about senior staff members. It. was. excruciating.”

4. Hanukkah balls

“I am a Jewish 26-year-old. I’ve been on the job about a year, and I moved from a large city to a smaller suburb of New York City for this job. My family is not super religious but we certainly never celebrated Christmas growing up.

My boss, a usually nice lady, has taken it upon herself to educate me about Christmas this season. She is super into the holidays, which I appreciated for Halloween, but has been declaring to the whole office how this is ‘Jane’s First Christmas’ and taking that opportunity to spend well over $500 on Christmas decorations which she has strategically placed mostly around her and my office. She has bought me my own Christmas stocking and ornament which says ‘Jane’s first Christmas’ with a date and her signature on it. She has placed red velvet bows around anything they will stick to and she has replaced our office coffee K-cups with eggnog. She has put up lights in the hallways and decked my door with some kind of tinsel that keeps sticking to my clothes and following me home.

She keeps reminding me what ornaments are and is amazed when I told her that I know the words to some Christmas songs.

She also has invited me to her home for Christmas because ‘no one should celebrate their first Christmas by themselves.’ When I mentioned something about celebrating Hanukkah instead of Christmas, she went out and bought this Hanukkah inspired contraption, which was really just eight round traditional ornaments with a light in each of them. She said they were Hanukkah balls.”

5. Hands off the holiday decorations

“One of my coworkers got holiday decorations banned permanently after he found all the human and animal shaped decorations (elves, Santas, reindeer, etc.) in the office and arranged them in compromising positions late at night.”

6. Keep your mom away from the holiday party

“My coworker’s mother decided it was a good idea to join us for drinks at our holiday party. She then proceeded to tell me how long it took her son to find a job, how it was not what he wanted to do or was good at, and how his lack of self confidence was due to the way his father treated him for most of his life. I wished I would have heard what she later on told our CEO.”

7. When your boss is the grinch

“Our team of five went out for a Christmas lunch last year and my (admittedly crazy) boss made a show of giving everyone but me a gift ($100 gift card each) …and then she made a show of pointing out how she didn’t give me one.”

8. Odd trophies

“I had a supervisor who was very unprofessional, and her being in her position was a bit of a scandal in the first place. Well, she decided to do an award ceremony during our holiday party, but instead of buying cheap trophies or printing out awards on paper, she went to all of the thrift stores in the area and bought a bunch of old Barbie dolls. She stripped them, spray painted them gold, and called them “trophies” that she presented to staff as an award. No printed certificate or anything to go with them, just nude, gold, spray painted Barbies.”

9. Holiday card misstep

“I very briefly worked at a law firm a few years ago, and my short time there included the holidays. A couple of weeks before Christmas, we all (about 15 employees) received a card with a prepaid Visa inside (about $25). The front of the card was a professional photograph of the managing partner with his wife and three children, standing in front of their enormous house out of state. One of the employees was his son from his prior marriage, who I am sure appreciated the beautiful photo of dad’s new family that did not include him.”

10. Holiday lies

“We had a fancy holiday dinner held at the boss’s house, and wine was served. My coworker’s husband takes it upon himself to get rip snorting drunk and tell the boss off for all the wrongs done to the coworker. The problem? None of those things actually happened. Apparently, the coworker would go home and tell her husband a bunch of sob stories about fictional incidents at the office, to get sympathy about her horrible day. She quit soon after.”

You think that’s bad? Check out the 10 Most Horrifying Team Building Exercises.

 

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  • I tried to keep my chuckles at the office as quiet as possible while reading this, but the golden Barbies got me good! I laughed and teared up a bit!

  • Rebekah Wells

    One year I was a temp admin for a group of district nurses, I was asked to , and happily arranged the Secret Santa (here in England, it’s a bit different, it is up to the individual Santa to reveal themselves, if at all, unless, of course, the office tradition demands they do not). After several days of sorting out the Secret Santa, I was asked if I was taking part, and due to the fact that I’ve had really awful experiences doing Secret Santa I said I was happy to just do the planning. After several people insisted, I finally agreed (very reluctantly). As I was the new person in the office, I said I was easy to buy for, I’d be very happy with dark chocolate Brazil nuts and a book voucher. What I got was a generic cat calendar and a cat cross stitch kit (yes I like cats, and yes, I do embroidery, very advanced, historically accurate, counted-thread embroidery). I was told to open it by my Secret Santa, who announced “It’s from me…” (She had never “done” Secret Santa before and was completely unaware of the protocol.) Suffice it to say, nothing what-so-ever could ever induce me to do Secret Santa again.

  • The Odd Trophies one made me literally LOL at my desk! Ack!

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