An Uncomfortable Holiday Moment: The Pumpkin Pie Surprise

We Asked for Your Most Uncomfortable Holiday Moments

To say that things don’t always go smoothly at family gatherings is really doing a disservice to the fine art of understatement. We’ve all had our moments of discomfort during the holidays. Over the next few weeks, Whalebone will be sharing some of our friends’ most squirmy moments and asking you to share some of yours as well. And who knows, we may pick some of you who share your uncomfortable moments and there might be something in it for you to keep you comfortable this holiday season.

Some of the names here are going to have to be changed to protect the innocent, but our first tale of holiday woe comes from a longtime friend of Whalebone:

Although we were allowed to drink mimosas before we were 21 on Thanksgiving morning in our house, I wouldn’t call our family gatherings necessarily interesting. We’d have pigs in a blanket and my dad usually has to take a champagne nap before the first football game is over.  However, one particular year stands out pretty distinctly.

My younger brother was back for his first family holiday since being deployed to Africa the year before. My parents, brother and I were so excited to have him back, last year was a little more boring without him and he was pumped to be around the family and not eat Thanksgiving dinner off of a metal tray. The thing is, he was going on and on about this new modeling job he’d gotten since he’d returned and, honestly, I couldn’t have cared less. My brother has a great heart but is extremely self-involved. So by the third or so time he brought it up we had just sat down to dinner, so I let him know that we stopped being impressed after the first time. That’s when he thought he’d countermand my protest. Real cocky, he said something like, “Oh, well, would it be more impressive if I told you it’s not really modeling?” I was on red wine numero 2, so I said, “Sure.”

Would it be more impressive if I told you it’s not really modeling?

“Are you sure?”

“Yes, dammit. We’re sure.”

“Great. There are cameras poses, but a little more action than you’d think.”


“I’m working in the film industry.”

“There’s no ‘film industry’ here.”

“Sure there is.”

“Oh, dear god.” Then things got really uncomfortable. “Adult ‘films?’”

He smiled and nodded. It was way too big of a smile.

And then my mom got up and had her first cigarette in three months. My dad might have high-fived him.

Then he accidentally told our grandparents at our older brother’s wedding later that year. I guess the work (or morning mimosas) keeps him honest.

Follow along at @whalebonemagazine for videos and stories of uncomfortable moments that might just make you appreciate your family a little more this year. You’ll also appreciate the delightfully comfortable things from Allbirds this holiday season that might come your way if you share your story with us.