the boudoir photos, the date from Shopko, and other stories of holidays at work — Ask a Manager

Here are 10 of my favorite stories you shared about holidays at work over the past month.

1. The empty gifts

For years we had a buffet dinner at a nice local hotel, and the room had decorations, including Christmas trees. Our Secret Santa was a version where you could choose and steal gifts but we didn’t unwrap until everyone had one at the end. People would smuggle their package in and under the trees, and we’d try to wrap them in enticing or misleading ways. It got quite raucous and was a lot of people’s favorite part of the event.

On the year in question, finally we were done and ready to unwrap, though a bit puzzled that there were still a few smaller gifts under the tree. Then some folks who had triumphantly walked away with large, impressive gifts opened them to find empty boxes marked things like TOILET BRUSH MULTIPAK. Of course it turned out the hotel’s decorations had included wrapped “gifts” under the trees and everyone just assumed they were someone else’s secret gift.

After that we asked the hotel to skip the boxes under the trees, and for years when we made the reservation and said this, their event planner would remember and start laughing.

2. The photos

My dad was a firefighter. They throw wild parties. Not officially Fire Department parties, they just happen to have a raging house party that could rival any fraternity, and invite everyone from work. The story I was told is that at one of these parties, Fireman Bob — who was in a prank war with Fireman Steve — snuck off to Steve’s bedroom and took “boudoir” photos on his bed. He yanked his tighty-whities up between his cheeks and took about a dozen Polaroid photos, leaving them fanned out on Steve’s dresser. Steve said nothing the next shift. Steve never did say anything. He didn’t have to. The next year, Steve gave everyone in the department a photo calendar, featuring Bob’s fancy pictures.

3. The secret

I was newly dating a colleague and we were at the holiday party Definitely Not holding hands. This was really kind of him since he would have been glad to shout our budding love from the rooftops, but as one of the only women at the company (and in fact the entire industry at the time), I was a lot more cautious. It was hard being cautious because he was really cute.

Spouses and kids were invited to this thing. The CEO asked someone’s nine-year-old if she was enjoying the party. She said, “Oh yes, I’ve met lots of nice people.” He asked who she’d met. Nine-year-olds have absolutely no chill, and she said, “I met your producer and your engineering director and your [my job title] and her booooooooooyfriend.”

All eyes shot to me and the cute boy standing an inch away from me. I blushed purple and he preened like a rooster.

My direct boss said, “Thank god, we can all stop pretending we didn’t know” and a chorus of “no kidding” came back in response from everyone in earshot. The CEO shouted out “I knew it!” (he didn’t). The CTO, who didn’t like women working at the company because we were “distracting” and once said out loud that there was no point in promoting women because we’d just get pregnant and quit, rolled his eyes and shook his head at me because clearly I was the only person involved.

To be fair to that misogynist ratbag, I have now been distracting that cute boy for 23 years and our youngest child is nine and blurts out secrets like it’s her job.

4. The oil painting

My coworker Donovan did a lot of art as a hobby, including oil painting and life drawing. As a joke one year, for our White Elephant party, he put in an oil painting he had done of his mother in the style of Napoleon. He put a note on the back stating something like “can be swapped for $25 Starbucks gift card”, but the person who ended up with it wanted the painting and wouldn’t give it back! That oil painting hung in the guy’s office for the rest of his time at my company. I can’t imagine taking it to a new company and having to explain that it’s an ex-coworker’s mother.

5. The photo

Early in my career I worked in government, in a department under an elected official, although my department rarely saw them because there were other departments under them that got a lot more press and public attention. My department’s relationship with that official was pretty poor, as she readily admitted that she didn’t know we existed before we got elected, and was eager to cut long-standing budget items of ours for short term gains. So relations with this person were not good, but we made our way to the annual Christmas party to try to foster some goodwill.

One year we did a white elephant gift exchange with all the departments, and while most everyone brought pretty tame mugs and gift cards, someone decided to bring in a joke gift, presumably because they were anonymous. I live in a part of the U.S. where you can get old-timey western portraits taken. The gifter had taken an old timey, lightly boudoir-ish photo of a madam and a cowboy in a saloon and photoshopped the elected official’s head on the madam and her male second in command’s head on the cowboy. I felt incredibly tense as this gift was opened and revealed, but it turns out the elected official thought this was truly HILARIOUS! She insisted on passing the photograph to everyone in the room, circulating it throughout the whole party. People kept putting it down somewhere but then she would pick it up and start showing it to people or asking them to pass it around again. To this day I have no idea if this was from someone who knew her well and knew she would like it, or if this was meant to mock her and failed spectacularly. But it certainly was the talk of the party.

6. The whiner

I have a colleague who is … well, let’s just say he’s a character. I’ll call him Dalì.

My company organized two Christmas events: one for employees only, and another for those with children (great for people like me who don’t have kids for whatever reason).

Dalì and his partner decided to attend the event because no one explicitly said it was for children (the event was called something like “Bring Your Children to Meet Santa”).

He proceeded to complain to everyone in attendance that the entertainment, such as face painting and arts and crafts, was clearly geared toward kids.

There was no alcohol, and Santa refused to let him queue with the kids to “have a chat.”

He didn’t like the food and thought that the small cups for babyccino were for mulled wine and he felt misled.

There is a glorious photo of him resentfully staring at “Santa” surrounded by children, holding a small teacup.

7. The date

At 19, I was the youngest employee in a large office. After the Christmas Party was announced, my coworkers began asking me, “Who are you bringing as a plus one?” Everyone else was married or partnered so they were VERY curious who my date would be.

Two weeks before I had gone to Shopko and had a great experience in their electronics department with one of their salespeople. Ryan was handsome, funny, and good at his job.

Now I needed a party date. I called Shopko, got transferred to the electronics department, and then requested Ryan come to the phone.

“Hi, this is (name). You sold me a portable DVD player two weeks ago and I had a question for you. Are you single?”

There was a long pause. “Uh, single? Yes.”

“Great! Will you come to my company Christmas party with me? I need a date.”

“Oh! Yeah, sure. I can do that.”

“What’s your number and I’ll text you the details? Thank you so much!!”

The night of the Christmas party, we met up outside the venue. Ryan had accidentally matched his tie to my dress so well it looked pre-planned. I asked him to pretend we had been dating a while since I didn’t want my older coworkers to know I had got him at Shopko the week before.

What I didn’t anticipate was the CEO greeting everyone as we walked in. CEO and I had few interactions but he prided himself on “knowing his employees” (even when he didn’t). Upon meeting Ryan, he said with a hearty handshake, “You must be (name’s) boyfriend! I’ve heard all about you. She’s one in a million, isn’t she?”

I froze. This was off script. What to do what to do what to do…

Ryan grabbed my hand and leaned into me saying, “Yes, I’m very lucky to be with her.”

The rest of the evening he played my boyfriend to all my coworkers. Charming, witty, everyone was so impressed with him. We lied our tails off about our marvelous fake relationship to everyone.

We walked out to the cars afterwards, I thanked him profusely, and then we never contacted each other again.

I waited until January and then told everyone at the office who asked, “How are things with Ryan?” that we broke up on New Year’s Eve.

It was the most romcom movie experience of my life and even now sixteen years later I am shocked it went as smoothly as it did to bring a stranger to my company Christmas Party.

8. The very bad party

I work for a public social service agency. A few years ago, some employees decided to have a holiday party; however, upper management decided we could not only not have a budget for something frivolous, but neither could we take non-billable time. So the committee compromised by having a … festive training event.

So we watched a presentation on elder abuse, and then sang a carol. Watched another presentation on the opiate epidemic, played a game. So on. For four hours.

We haven’t tried having a holiday party since.

9. The truth teller

One year, grandboss thought it would be nice if people brought their kids to work for the holiday party, which was immediately after work. This caused some grumbling as a lot of parents had to commute home to pick up their kids, then come back again.

It was all worth it, though, when grandboss asked the young (I’d guess 7-9 years old) son of one of our employees, “What do you think of the holiday cookies?” and junior replied, “They taste like shit!”

Several of my coworkers couldn’t contain themselves and ran off to the break room to laugh. The mother of the kid was, of course, mortified and said “[name], we don’t use that language or say things like that, it’s rude” to which junior replied, “But you told me to always tell the truth!” which elicited even more laughter.

10. The fancy dinner

I’m a doctor and I’m Jewish so I always work Christmas. I don’t celebrate and it makes no sense for my colleagues to miss time with their loved ones so I can eat Chinese food in my pajamas. Also it meant I never had to go to my (non-Jewish) mother-in-law’s for the holiday.

My first year out of residency, I worked 8-6 Christmas day. My best friend was a senior resident working nights that month. We would otherwise have had dinner with her and her husband, so we decided to bring Christmas dinner to the on-call team. She lived a block from the hospital so her husband cooked the turkey and sides that had to be hot. My husband did the salad and dessert. He loves to cook and he hates football and he was alone all day and bored so he decided to make the fanciest dessert he could think of and created a Black Forest cake from scratch – three layers including glacéed cherries and chocolate curls. The guys arrived with all the food at 5:30 and we sat down at 6 – eight residents, me, and the attending who took the night shift after I went off. She was stunned to arrive and find an entire Christmas dinner laid out complete with tablecloth, good china, and flowers.

She was even more amazed to discover that the husbands had cooked it. She clearly believed that men were physiologically incapable of making stuffing or from-scratch rolls or creamy mashed potatoes. Then the Black Forest cake came out and she just stared.

When we packed up and went home, my husband and I agree that we had probably made life much more difficult for her husband.