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I Took a Tinder Date to My Office Holiday Party

I figured that if he was the kind of person who’d agree to a first date at a stranger’s company holiday party, he was the kind of person that I’d get along with.
woman on floor at holiday party
Photo by Gpointstudio via Getty.

Every year, my work wife at my day job in tech bugs me about whether I’m bringing someone to our company holiday party—I know to expect this line of questioning from her as soon as the RSVP email goes out. Every year, I say no. I’m not sad about being single, nor do I feel the pressure of taking part in cuffing season or to enter relationships solely for the sake of being in them.

I am, however, someone who happily attended a furry convention just because, made my stomach pooch its own Tinder profile (that’s a story for another time, but my li’l jelly roll got action!), and agreed to go on a Hawaiian vacation with a dude whom, at the time, I’d only known for eight weeks. Suffice it to say that, at this point in my life, I prefer the weirdness and unpredictability of dating more than I wanted a steady partnership with some dude who’d probably never been to therapy.


That’s why, last year, I decided to invite a complete stranger to my office holiday party. I didn’t mean to at first—I had just started a year-long road trip and was only going to be in New York for a few weeks, so scheduling meet-ups with Tinder dates was tricky. I’d matched with a brunette, bespectacled dude from Brooklyn who sent me YouTube links to videos that made me die laughing, and we both wanted to meet up. He suggested we get together the Friday of that week, and since I didn’t have a lot of free time, so I told him, “Technically, I’m not free…but I could be if you don’t mind meeting me at my company’s holiday party,” throwing in an “lol” for good measure.

All of a sudden, I was secretly hoping he’d say yes so I could finally shut my work wife up, and because I thought it would be hilarious. So, when he agreed, I was pumped—I figured that if he was the kind of person who’d agree to a first date at a stranger’s company holiday party, he was the kind of silly, impulsive person—like me!—that I’d get along with, right?


On the afternoon of the party, nerves set in as I changed into my dress and heels (the latter of which I only wear once a year, for this very occasion). It hit me that this man I’d never met was going to be my date among my 100-plus colleagues at my day job. What if he was reserved and slunk off to sit in a corner the whole night? What if he got completely sloshed and hit on our head of HR? If he acted up, this motherfucker would be a reflection on me. Oh, god. What had I done?


I felt tempted to text and apologize for having had this dumb idea in the first place, but my dedication to a joke knows no bounds. What was the worst that could happen? I’d lose my job? (I did my best not to entertain that thought too seriously.)

When I sat down at the employee-only dinner before the party, I guess my nerves weren’t too bad, because you bet your ass I ate every bite of my filet mignon (having a job in tech has its perks). I sat next to my work wife, who, when I told her about my plan earlier that week, wasn’t happy that I had taken her request to get a date and completely Dana-fied it. “I absolutely cannot stand you,” she told me as we indulged in the next course. She wasn’t exactly surprised, though, considering my department’s nickname for me is Chaotic Evil.

Finally, 9 pm rolled around and, right on the dot, I got a text that my date was in the foyer of the fancy SoHo restaurant. That’s when I turned the corner and saw he was in a mesh tank top, A.C. Slater style…at a company holiday party.

Just kidding. While I wish I had a shocking story about how the night went, it ended up great! When he first arrived, he got a drink and we sat chatting out on the patio under some heat lamps while I partook in my Dana-fied version of a glass of wine (I brought my Pax with me). We asked usual first-date questions, but mostly bonded over the ridiculousness of the situation. Feeling merry and bright, we went out on the dance floor and pretty much didn’t leave until the party was over. He briefly met some people (I got a kick out of introducing him to my coworkers as “I do not know this man, please help”), but for most of the night, we got down to the 90s R&B. From time to time, I caught my work-wife side-eyeing me as she danced with her girlfriend, shaking her head and chuckling.


Before the party was over, my date solidified his “good sport” status by enthusiastically agreed to take pictures with me at the holiday photo booth my company had arranged. As we headed out around 11, a happily buzzed C-level executive hugged us and told us he loved us.

my tinder date and i at the office holiday party

Photo courtesy of Dana Hamilton.

It worked out well because both my date and I knew dating isn’t serious. We shared the philosophy that if you’re not having fun, you’re doing it wrong. Have I ever had a guy subject me to a seven-minute recording of him performing slam poetry (OVER THE SOUND SYSTEM OF HIS CAR; cut to me contemplating opening the door to tuck ’n’ roll) or another show up violently hungover (where I proceeded to pop an edible and cry laughing as he told me he’d cheated on everyone he’s ever dated)? Sure. Was it still hilarious? Absolutely. I don’t have bad dates, only good stories.

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The party was a success, but I didn’t feel any romantic vibes, so I said thanks for tagging along and never saw that dude again. The next day, I was Single Dana again—good ol’ Chaotic Evil, free to create more memories with new, interesting strangers—a holiday gift I was more than happy to receive, professional reputation intact.