Should You Travel With Your Work Bestie?

While not all trips result in ruined friendships, the potential fallout is even trickier to manage when your colleague's involved. Content strategist Cherry Tan learnt her lesson the hard way.

If you’re reading this, you probably have a work bestie whom you grab lunch with, gossip with, turn to for advice, and miss while they’re away on vacation.

My work bestie, Rica*, and I bonded over tough times. We also motivated each other to attend 7am gym classes, and trusted each other with the ups and downs of our love and family life. We’d often joke about being colleagues-turned“real” friends.

When Rica suggested that we travel together, I thought: What could go wrong? We ended up being so busy that we didn’t have time to discuss the trip in detail, but I was confident we’d figure it out along the way.

Turns out, things weren’t that simple.

The one-way trip down south

For starters, Rica nestled her head on my shoulder to sleep on in the plane, without warning. While we were close, this level of physical contact had never been a thing between us. I also felt uncomfortable at the invasion of my personal space. When she finally realised I wouldn’t keep still, she clicked her tongue audibly and turned to rest on the window instead.

A few days later, there was a loud passive-aggressive groan when I entered our hotel room past midnight, followed by another louder one as I began washing up in the bathroom. While she was aware and fine that I’d be returning late that night, I felt a mix of self-inflicted guilt and resentment. I ended up skipping my shower, going to bed after only brushing my teeth. Gross, I know.