Ah, it’s Wednesday morning, and here you are, gritting your teeth through your fifth meeting of the day. Tim is busy playing his favorite sport: interrupting. Meanwhile, John is hard at work “mansplaining” your project as if he’s a TED Talk speaker. And let’s not forget the delightful surprise of being tasked with organizing Vera’s birthday party—because who doesn’t want to add “party planner” to their résumé before lunch?
As you mentally brace yourself for the rest of the day, a comforting thought crosses your mind: what if your partner were sitting right next to you, sharing in this corporate circus? Well, I can’t say I’d be thrilled about that.
Working in tech can feel like wading through a sea of less-than-stellar copies of Mark Zuckerberg—though I’ve yet to see one that inspires a right swipe. The search for decent dating options sometimes seems akin to finding a needle in a haystack, albeit one tangled with questionable online profiles.
This leads me to ponder the allure of workplace romances—those forbidden fruits of the office jungle. Though dating a coworker is considered controversial, let’s not overlook the perks: like sharing those delightful rides to work, lunch dates that won’t cost you a dime if your company has catering, and the bliss of discussing office gossip without the need to explain who, exactly, John is or what catastrophe he’s caused this week.
Elisha Tan is a Singaporean comedian based in the US.
Perhaps the greatest allure of dating a coworker lies in the shared understanding of our chaotic lives. My days are spent in a tech world, while my nights are consumed by stand-up comedy—like living in a frat house where the majority are men. If I had a partner from work, they’d understand my late-night escapades without raising an eyebrow.
But wait, isn’t sharing your soul—and your office printer—with a partner in the same location an invitation to HR’s watchful eye? Surprisingly, with all the perks, the question remains: why don’t more people give in to this tempting proposition?
The Search for a Work Boyfriend
Let’s kick things off with the most ancient challenge of workplace romance: How on earth do you find out if that cute coworker is single? Rings are apparently no longer fashionable, leading to way too many awkward moments. I mean, I once flirted with a colleague I assumed was available, only to discover he had a fiancée who could easily walk the runway—talk about a facepalm moment!
Reeling Him In (Without HR Not Noticing)
Let’s talk flirting in the office—it’s like walking a tightrope over a pit of snapping crocodiles. A friendly chat could easily veer into the “Harassment Zone,” creating a career nightmare. I remember once jokingly telling a coworker I was going to “hook up” with him post-dinner—definitely not the kind of thing to say at the breakroom fridge. Had I misread the situation, it could’ve ended with me joining a career pivot into the world of cat memes.
After the Break-Up
And what if the relationship goes south? Preparing for an awkward run-in with your ex is as uninvited as a sneeze-induced leak. Depending on how your love story concluded, it might lead to more awkwardness than an all-hands meeting around the water cooler. I once dated a comedian who ghosted me, and running into him at shows afterward was like living in my own horror movie. And can we talk about when you run into them with your new partner? It’s a reality show plot twist no one asked for!
Ultimately, workplace romances are like shopping for ice cream in the grocery store. You might find a tempting flavor, but it’s essential to consider the “calories” you’ll be consuming in the process. So should you dive into the romantic pool at the office simply because it’s convenient? Welcome to my existential crisis—the reason I’m still single, daydreaming about what could have been while sitting through interminable meetings.
Elisha Tan is a regular big tech employee and an up-and-coming Singaporean comic based in San Francisco. She has graced stages at Cobb’s Comedy Club, Laugh Factory, and various international shows. Elisha also founded the Average Foundation, a community fund supporting small social impact projects. Catch her antics on Instagram (@elishatan).
