This post, the ancient fruitcake, the murder mystery lunch, and other times holidays at work went wrong , was originally published by Alison Green on Ask a Manager.
Earlier this month, I asked readers to share your funniest office holiday party stories and funniest office gift debacles. Here are 15 of my favorites.
1. The statue
Was invited to my bosses house for an employee holiday party. This small business was owned by a married coupled who were also landlords, so they were pretty wealthy and had a huge house. I was walking around admiring their art when I cam across a statue.
A nude statue.
A nude statue of my boss.
2. The dance
Our CEO loved hosting the annual Christmas party as he felt it was his personal thank you to all of the employees. He would spend weeks planning out the decorations, tasting food for catering, hand selecting the gifts, and always made sure there was a huge open bar with premium drinks for everyone to enjoy. The party started at 7pm, ended at 12 am, and then he would do an extended “after hours” party until 2am. Needless to say, people wound up pretty wasted at these parties and the CEO was the most wasted every year. Luckily, he was a happy go lucky type of drunk who usually just ended up thanking everyone profusely for their work.
One year the dance floor was pumping and everyone was having a grand old time when the DJ decided to play “(I’ve Had) The Time of My Life” (you know, the song from Dirty Dancing). Suddenly the dance floor parted. The CEO stood at one end of the dance floor, zoned into the music. The VP of Sales locked eyes with the CEO and they began to fully run toward each other, each clearly assuming the other would catch him. They leapt into the air with drunken grace and enthusiasm. ::smack:: They landed on the concrete with a smack you could hear over the music and crowd. All we could see was some blood and two bodies trying to untangle.
They had both cracked their heads on the ground and gotten concussions. Neither gentleman wanted an ambulance called so someone’s sober wife packed them into her SUV (each of them with a roadie in-hand) and drove them off to the ER.
The next day we got an email from the CEO with the subject, “Each Year Gets More Epic” and a picture of him and the VP of Sales posing together at the ER with stitches on the side of their heads.
3. Not a pickle
One year, I was The Pickle Lady. I was obsessed with pickling, especially lacto-fermented pickles. I pickled anything I could get my hands on and, since my pickling was so prolific, I often shared the fruits of my labours with people in the office. I also talked a lot about pickling and would happily offer guidance to anyone seeking the way of the pickle. This also expanded into talking about making vinegars and kombuchas, and I freely offered bits of my SCOBYs to anyone who would ask. I often joked that I was the Queen of Controlled Rotting. In retrospect, I was probably a little obnoxious, but it was all in good fun.
One sweet, lovely coworker watched all of this happen without engaging with me about it much, so she must have misunderstood how fermentation works. She picked me for Secret Santa that year and when the office got together to open gifts, I ended up opening mine near last. It was this beautiful gift bag, just to my taste, and I pulled out my gift to find… A jar of mold. Just grey-green fuzziness throughout the entire jar. I was deeply confused and not originally sure what it was, so I tentatively opened the jar. The smell was eye-watering to say the least, and it quickly spread to those around me. They reacted with a mix of polite confusion, low-key revulsion, and concealed amusement. After a few jokes and confused noises, we all made nice, set the jar of life aside, and moved on with the party.
Later the coworker came to me, red in the face and with tears in her eyes, asking why everyone had hated her gift. I asked her to clarify what it was supposed to be. She said she knew that I loved all this “controlled rotting” business, so she had put some of her favourite foods in a jar and let them go bad in the hopes that I could use the mold to make my own treats. That way it would be like we were making them together. It was so adorable, so endearing, so loving, and so misguided. I thanked her for her intentions and we were eventually able to laugh about the misunderstanding.
Now I love to tell the story of the time I was gifted a jar of mold.
4. The sink
Years ago my office holiday party was held in one of the company buildings, which had a single person restroom. Everyone had a good time and the drinks were aplenty, but no shenanigans (or so we thought). The next day, one of employees sent out a photo he took at the end of the night of the bathroom sink completely torn off the wall and smashed on the ground. Nobody fessed up, but at the time I had access to the security footage so the IT guy and I checked it out. We saw our HR manager go into the (remember, single person) bathroom with their partner and then both snuck out several minutes later. The next person to go in was the one who sent out the photo. I don’t know what was going on in there, but hopefully it was worth it!
5. The questionnaire
When my office decided on a Secret Santa gift exchange, we all filled out short questionnaires (clearly labeled as being for the Secret Santa) that gave us an opportunity to describe things we like and don’t like. I drew my coworker’s name and was curious to know what she’d put about her likes/dislikes. This coworker, despite being very good at her job in many respect, was known around the office as someone who occasionally needed to be reminded to slow down and listen to or read the entirety of what someone was saying before speaking/acting. So I should not have been surprised to see that she’d listed her likes as “walks on the beach” and “sunsets,” or (my personal favorite) “making love.”
6. The finger
One year the office holiday part coincided with a visit from the company’s CEO (we were a satellite office), so the party planning committee had the brilliant idea to bring our ~40 person group to the bar on the top level of the Hancock Building in Chicago. Nice and fancy in theory, but the drinks there are so expensive that we were only budgeted for one each, and it’s really not a very big bar so it was very awkward fitting us all together. Things got worse when the CEO decided to make everybody go around and share what they hoped to see for the future of the company (so festive!). Suffice it to say the vibe was already very weird by the time we were ready to leave. I ended up taking the elevator down 95 floors in the same group as the CEO, who had been chatting with one of my office’s sales reps, and for some reason he pointed his finger at her while talking and, to the horror of the rest of us crammed in with them like sardines, she leaned forward and took his whole finger into her mouth. I have no idea why (not alcohol; we’d all just had the one weak cocktail apiece) but the stunned silence and awkward glances lasted for the rest of the ride.
7. The terrible cards
The worst corporate Christmas cards I’ve ever come across:
– Every year the CEO wrote everyone (100-ish people) a card with a quick message. This is a sweet idea.
– One year, the Design Director said she would design the cards. Also a fairly sweet idea.
– What she came up with was the weirdest card I’ve ever seen. No concession to Christmassy themes whatsoever. Dingy grey background with a checkbox list of the company values, so the CEO could tick whichever value he felt you most embodied. Sort of sweetly-intentioned (?) but deeply weird.
– So she gets the cards printed and drives over to the CEO’s house with them. They crack open a bottle of wine. They work through the cards. Tick, message, sign, tick, message, sign. There are worse ways to spend an evening, I guess.
– Except. For at least two people, he FAILED TO TICK ANY OF THE BOXES. So those two (at least) employees get a dingy grey card implying that the CEO does not think they embody any of the company values. NOT GOOD.
– A few days later, the Design Director sends out a very sheepish apology email.
8. The pet pictures
Job before last, my very shy, reserved coworker had a biiiiiiiiit too much to drink and went around the room demanding that people show her pictures of their pets. (This included the CEO, but fortunately he thought it was hilarious.) It culminated with Drunk Coworker bursting into tears when she was told one of our other coworkers didn’t have any pets, and saying, “You’re so nice, you deserve to have a dog.”
(She was mortified when we came back to work, so we didn’t tease her about it… much.)
9. The lap dance
My significant other’s holiday party is NIIICE. Lots of good food, like excessive amounts and lavish displays of every appetizer, main dish, etc. you can think of. The same with the alcohol and open bar, there literally isn’t a bottom shelf option. No Bud Light. No cheap vodka. No Two Buck Chuck wine to be had. The dress code is relaxed and ranges from tailored suits to guys in Carhart hoodies. It’s a work party that we actually look forward to because it’s so laid back and we really do have a good time. The last one was in 2019, and it may be the last one period. Or at least the last one where drinking isn’t monitored.
At the last party, an employee’s guest decided to give his girlfriend a lap dance. In full view of, well, everyone. People around the couple were half-heartedly trying to get him to stop, but they increased to frantic levels of “OMG STOP!” once he took his shirt off and could tell he was fully committed. Eventually someone got him to stop by tackling him to the ground with his pants around his ankles and his belt still in his hand, waving it around like a lasso.
10. The very bad writer
I was working for a vacation real estate company and we had a pretty big problem with the admin who did the newsletter/marketing/emails. She would NOT let anyone proofread her work or even allow anyone to correct anything and she had ZERO understanding of synonyms and misused words all the time and misused things like LOL and LMFAO, and also created her own bizarre shorthand to such an awful extent that it caused confusion, hilarity, and in some cases, offense and loss of business. Long story about the layout of the company, but we also had some rental units on-site for prospective buyers and a small spa, cafe, and bar. You know, vacation town stuff. She also did the menus and all the holiday announcements. This one was, and will always be, my favorite. It went out to over 15k former and current buyers and clients, inviting them to the company holiday party:
Cum celebrate our Holiday Szn with Secrete Santa! Fist four clients up and get a free giraffe of wine at their table!
What she was TRYING to say was that during our Secret Santa dinner and raffle, the first four clients who entered would get either a complimentary wine to take home or a carafe of wine at their table. Some other gems on the menu included “gooze breasts” “Bef stek” “Coozeberry Jam” and my absolute favorite “fresh tilabia.”
Some people thought she did this on purpose, I know for a fact she was just an absolute idiot.
11. The murder mystery lunch
My department went to a local, beloved restaurant as part of our holiday outing. We were going to go to their Holiday Murder Mystery lunch where, we assumed, we’d eat lunch while the play was going on. I personally thought there might be a little audience participation required but nothing like what we encountered.
Firstly, when booking the lunch, we were sent a picture of the room we’d be in. It was spacious and well-lit and beautifully decorated! When we got to the restaurant we were escorted into the basement where there were no windows, dim lighting, and a dingy bar. As we sat there, the actors came out dressed as elves, reindeer, and Mr. and Mrs. Claus. The costumes looked like they were picked up at the Halloween Store discount sale and smelled like they hadn’t been washed in years (yes, I could actually smell them). They moved from table to table, “in character” and even sat down with us many times… where they stayed for several minutes. Now, I can appreciate the work and skill it takes to improv but after about 10 minutes all I wanted to do was drink my Diet Coke and wait for the actual performance to start – not be forced to talk about Santa’s dismissal of labor laws with a guy in tights. After about 15 minutes of this I realized, with great horror, that this WAS the performance. These actors were going to improvise a play about a murder in Santa’s Workshop for the next 2 hours.
It. Was. Dreadful. I have never been so uncomfortable in such a “festive” setting. The most surreal part was when they would make dirty jokes and break into song. A guy dressed in a muscle suit with reindeer antlers on his head gyrated behind me as I stared intensely at the table. If there was a crack in the floor, I would’ve slid into it.
What made it worse was the fact that the poor waitress (who apparently been pulled aside at the last minute and told she was going to be waiting on 30 people by herself), was struggling to take orders that we had already placed when we booked the event. We got there at 12pm and by 2pm, we still hadn’t been served. Not only that, but no one had been murdered yet!
When we finally got our food, I realized that things were not going to get any better. The food looked like it could get up and walk away and the dessert was, what I assumed to be, canned apple pie filling with Redi-Whip on top.
We got a break from the show while we ate (or chose not to), at which point we were forced to tell the actors that we had to be back on the bus by 3pm and someone had better get murdered soon. They picked up the improv pace and the workshop inspector faced death-by-wrapping-paper. We were given pieces of paper to write down who we thought did it and turned them in. The motive behind the murder was of a sexual nature, which I thought was a bit inappropriate for an office outing, and we were able to get out of there in time to get back to our bus.
We complained to management but were met with not much more than a shrug. If the food was at least decent, I could’ve brushed off that cringe-worthy “murder mystery” but, alas, there was really nothing redeeming about this outing. Except maybe the waitress, who has my condolences.
One place I worked had a fruitcake of undetermined origin which had been passed around for at least 10 years (longest tenured employee remembered it at her first holiday party, but it had been there prior to her). It had a name (Phillippe). Whoever won it built a shrine to Phillippe in their cube and proudly displayed it until the next year… Might have been a cheap gag gift, but dang the competition for Phillippe was intense.
The end of Phillippe’s story: An intern won it one year after I left and hadn’t realized that this wasn’t supposed to be eaten. Apparently Claxon Fruit Cake is still edible after at least 13 years. She brought Phillippe II for the next gift swap … All interns are now warned not to eat Phillippe II.
13. The perfume
My father’s story from a good 25 years ago. One time he’s telling us about what gifts they bought for all the staff. It was perfume (don’t get me started on the gendered nature of it, that’s a whole other thing) but one he didn’t recognize, and the salesperson from somewhere like Macy’s had “recommended” to him. He’s telling us this, and says it’s called something like “plah-sen-tay” like it’s French, he thinks (shades of A Christmas Story here). My mother and i start snickering. Really dad? She recommended it? And you said sure, sounds good? And he’s saying what, what? as we started laughing so hard we were crying and falling out of our seats at Boston Market… because he apparently had no idea he’d bought every woman on his staff PLACENTA perfume. Like something that had that in it, and it was maybe supposed to be a beauty aid? It was unclear, but we surmised that the salesperson had a truckload of this stuff to unload and could tell he had no idea what he was doing. He sits there horrified, and reflects, “Huh… i was wondering why people seemed a little weird about it. There was a lot of talking in hushed groups afterward.”
14. The buffalo
I’d been working in an office that would do the yankee swap/dirty santa style of gift exchange, where folks could steal a gift from each other. One year someone had found a photograph of a couple of water buffalo in their office. It was a BIG photo, framed, close to three feet wide. The water buffalo were pretty scroungy and dirty looking. It was not an attractive photo! But wrapped up, it looked like an impressive gift. As someone found out the hard way when they “won” it.
I thought it was pretty funny in its awfulness. So the next year I deliberately took it, and hung it with pride in my office.
The next year I hid the photo behind a couch in the party room, and then added my “gift” to the swap: A small, wrapped box, that held a note, “You won the buffalo photo.” I can’t remember who won it, but they were not amused.
I went back to visit, years later. There were the buffalo, hanging over a colleague’s desk. Everyone who had gotten it since had signed and dated the back.
15. The apology
Quite a few years ago, my husband and I attended a Christmas party at a local hotel, put on by the construction company he worked for. It was the first year we’d attended and because of past instances of drunk driving, the company had not only paid for the catered meal but also reserved rooms for all the attendees.
Among the highlights of the evening were the multiple escorts who were hired to attend with guests. One of them ended up sitting at our table. Her ‘date’ had hired her because he had recently broken up with the boss’s daughter and didn’t want to be seen attending alone. He proceeded to get drop-dead drunk on the table wine, and boozily monologue about his romantic difficulties. Full credit to the escort, she was among the best company at our table and when she wasn’t babysitting her maudlin charge, was a lovely conversationalist.
But it wasn’t until after dinner had concluded that the wheels *really* fell off the bus. To this day, I don’t know exactly what some of the attendees *did* in the indoor swimming pool that necessitated it being drained, but my husband says the clean-up charges were in the thousands. Being confirmed non-partiers, Mr. Jam and I were eager to avoid the impending trainwreck and when we were invited back to his co-worker’s suite to join three or four other of the more down to earth employees, we were anticipating fun, low-key evening playing cards or shooting the breeze.
We get to “Mike’s” room and settle down on the sofa. While we’re chatting, Mike suddenly grabs this duffle bag and starts rummaging around in it. I assume he’s eager to get out of the monkey suit but that’s not what was packed in his luggage. Instead, he starts organizing these thick baggies on the coffee table in front of us. Folks are making themselves at home, and he’s pouring what must have been hundreds, if not thousands, of dollars of hard drugs onto the table six inches from my knees. He’s chopping and chatting and telling jokes and all the while, he’s making little white lines, like he’s playing in Pablo Escobar’s sandtable!
I have no idea what to say and just want out of this awkward encounter. Mr. Jam and I have a frantic, yet totally silent, marital conversation, consisting entirely of raised eyebrows and shoulder shrugs, the result being my developing, quite out of the blue, a sudden and blinding headache from the half glass of red wine I’d had earlier at supper. Alerted to my suffering, Mike generously offers me a thick joint, promising that it will fix whatever ails me, but I decline very politely and retreat with all haste back to own, blissfully drug-free hotel room.
After I leave, Mike apparently realizes just what he’s done to make me so uncomfortable and he begins apologizing profusely to my husband on my behalf. You see, while he’d been cutting the hundreds of dollars of cocaine right in front of us, he’d also been telling a mildly off-colour joke, the punch line of which included a word that rhymes with truck. Clearly, my delicate ears couldn’t bear to hear such salty language. Mike’s apology went on and on as he promised my husband with absolutely sincerity that in future, he would remember to watch his language more carefully whenever he was around me. Mr. Jam assured him that I wouldn’t hold the joke against him, I was just especially sensitive to bold reds, but Mike remained doubtful.
And then there is this party coda. A few years later, after my husband had been gone from the company a couple of years, we chanced to run into ‘Mike’ in the parking lot of a big box store. In between inquiring about our kids and Mr. Jam’s new job, he once again took the time to apologize to me for the joke he’d told all those years earlier. Neither of us mentioned the drugs!
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