From The Straits Times    |

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It’s Wednesday morning, and you find yourself in your fifth meeting of the day. You’ve already navigated Tim’s continuous interruptions, John’s repeated attempts to “mansplain” your project, and the unexpected responsibility of organising Vera’s birthday celebration, despite it being outside your job description – all before 11 am.

As you dread going through the rest of your day, you can’t help but wish for a comforting hug. Just imagine if your partner were there beside you in the office at that very moment. I can’t.

Working in tech, I often find myself surrounded by less remarkable versions of Mark Zuckerberg that are likely to inspire one to swipe left – and into the black hole of profile rejects.

I often ponder whether workplace romances are the forbidden fruit of my professional life. While dating a co-worker is a controversial subject, it’s worth considering the advantages it brings, such as convenience. Imagine sharing taxi rides to and from work, enjoying lunch dates at the office (for companies that provide meals), and freely discussing workplace gossip without the need to explain who John is and what he did – the list goes on.

Elisha Tan is a Singaporean comedian based in the US

However, the most significant advantage is sharing a common context. For instance, I work at a large tech company during the day and pursue stand-up comedy at night, which keeps me incredibly busy. It often feels like living in a fraternity, since I’m constantly surrounded by men – whether at work, networking events or social gatherings. A partner from my workplace would understand that this is a normal part of my life, even if I’m out with them until 2am. Both tech and comedy are male-dominated fields that rely heavily on building relationships.

While men outside of my workplace can be equally understanding, a partner in both life and work can offer something they can’t – tangible support, such as mentorship and networking. An insider is in the best position to directly assist your career. With all the benefits that come with a workplace romance, why isn’t it more common?

The answer lies in the tricky path to a successful workplace romance.

The search for a work boyfriend

The first challenge is the search – how can you determine if a co-worker is single? Many people no longer consider wearing a wedding ring fashionable, leading to numerous awkward encounters. I remember a particular incident when I attempted to flirt with a male co-worker whom I believed to be single, only to later discover that he had a fiancee who was far more attractive than me. Ouch.

Reeling him in (without HR noticing)

Flirting can be challenging, and it becomes even more complex within a workplace setting. A misinterpretation of friendliness can lead to awkward conversations, while poorly executed flirtation can be misconstrued as sexual harassment. I recall an incident from many years ago when a co-worker asked about my plans after dinner (normal), and I jokingly replied that I was going to “hook up” with him (not normal). While I can laugh about it now, it could have resulted in a disastrous career outcome had I not correctly gauged the situation, and it could have been even worse if our genders were reversed. Even if things progress smoothly, there’s a third party in your relationship – Human Resources. In certain workplaces, HR must be notified about your relationship. Furthermore, let’s not be naive: Office gossip will inevitably circulate, especially if you and your partner work closely together, like in a manager-report relationship or on the same team.

After the break-up

And if things don’t go well, running into your ex at work can be as common as experiencing the occasional sneeze-induced pee leakage (let’s be honest, ladies, this happens to you as well). Depending on how gracefully the relationship ended, it could have real repercussions on your career, not to mention the awkward encounters. I recall a time when I briefly dated a comedian who chose to end things by ghosting me. It was uncomfortable running into him at shows and, needless to say, I wasn’t inclined to recommend him to any show producers! Now, as an unexpected sequel to the story that nobody asked for, you may also cross paths with your ex at work while you’re with your new partner. These are just some of the situations you need to be prepared to handle. Ultimately, workplace romances are a bit like being at the ice cream section of the supermarket. You are faced with an array of delicious choices, but you have to consider the calories and whether they’re worth it. Should you pursue a workplace romance simply because it’s convenient? I’m still trying to figure that out for myself. Perhaps that’s why I’m still single, sitting in meetings and daydreaming about the what-ifs.

Elisha Tan is a regular big tech employee, and an up-and-coming Singapore comic based in San Francisco. She has performed at Cobb’s Comedy Club, Laugh Factory, and clubs and shows internationally. Elisha also founded Average Foundation, a community fund supporting small social impact projects. Follow her on Instagram (@elishatan).