I, A Straight Guy, Was A Drag Queen For A Night. Here’s What It Taught Me
All images by kairosnapshots.com.

Mary May.

A week ago, she showed me that I could do things I never thought possible. For a few hours, we were perfectly in sync and our hearts beat as one. I was her. She was me.

This isn’t me describing a passionate night of intense love-making. Rather, it was my experience of doing drag last Saturday evening.

Under the tutelage and guidance of professional drag queen Becca D’Bus (Eugene Tan in real life), I dived into the world of drag culture, eventually performing as my alter ego Mary May in front of a paying audience.

It was one hell of a ride, and here’s what I learnt.

Dressing in drag ≠ being a drag queen.

As a guy with absolutely no knowledge or experience with drag, one major stumbling block happened before I even met my mentor.

Upon receiving my assignment, I had been advised to start my journey by thinking of myself as a character, and to go from there. But it made absolutely no sense to me. I mean, all I had to do was slap a little makeup on, slip into a dress, and be fabulous right?


After sitting down with Becca and learning about drag culture, I discovered that there was a thick, mascara-ed line between simply cross-dressing and being a bona fide drag queen.

Yes, you can’t technically be a drag queen without dressing in drag. But merely looking like the catholic-schoolgirl version of Britney Spears on Halloween is far from enough.

You see, while Eugene doesn’t shy away from including skirts in his day-to-day wardrobe, it’s just a fashion choice when he’s not performing. On the other hand, being a true drag queen is about creating a persona specifically meant for an audience, and embodying it on stage.

The second a glittered toe is presented to the crowd, your true identity ceases to exist for the entirety of the performance. You are supposed to become a completely different person. After hearing Becca explain all of this, it finally dawns on me why creating a character is necessary, and how important it would be.

Rather embarrassingly however, that fact only really hit home a few hours before I was scheduled to go on. My friends and colleagues might have known the man behind the copious layers of foundation, but to everyone else, I was Mary.

They had paid to watch her, not me. I just had to give them their money’s worth.

Drag is freedom.

Because there are no hard and fast rules on what constitutes a “proper” drag outfit or performance (except Becca’s sole commandment of “not sucking”), the possibilities were endless. I could literally be and do whatever I wanted and it was amazing.

Yes, having that much freedom posed its own set of challengesfrom having to make decisions on everything ranging from the type of shoes I was going to wear to the colour of my wigbut on hindsight, I’m grateful for even having those choices.

In today’s day and age, where we’re still constantly told to refrain from doing certain things and/or to behave a certain way, the liberty that comes with doing drag is one amazing “fuck you” to societal norms and expectations.

It was a refreshing breath of fresh air and I’m pretty sure you’d be hard-pressed to find the opportunity to reinvent yourself in this same way anywhere else.

Ironically, it also took being someone else for me to remember who I am.

Drag queens say whatever they want and are hardly (if ever) sorry about anything they do while in character. They’re brash, loud and unafraid to call it as they see it. And it’s precisely that which makes them so entertaining to watch.

Now I’m not saying that I’ve become an advocate for absolute free speech. But if anything, it was a pleasant reminder to never feel ashamed of having, voicing, and standing by an opinion.

You’re bulletproof once you learn how to laugh at yourself.

If there’s one quality that all drag queens I met that day not only share, but possess in abundance, it’s the astonishing ability to laugh at anything and everything. Especially themselves.

In drag, self-deprecation is the name of the game. These guys know that they’re pretending to be something they’re not, yet instead of sweeping it under the rug, they shout it from the rooftops.

Everything is exaggerated for comedic effect and they aren’t afraid to take anything to the next level. From my experience, I’d even go so far as to say the phrase “playing it safe” doesn’t exist in their vocabulary. To hell with playing the role of an average girl-next-door. These guys are out-and-out divas.

Drag queens also couldn’t care less if their audience is laughing with or at them. The minute you walk in the joint, they know that your attention is theirs. They bask in it and own the crowd, regardless of what you think of them.

That level of confidence is only possible because they know how to first laugh at themselves.

Backstage, as we were waiting for the seats to be filled and the show to start, personal jibes flew all over the place. But no one ever got offended. Instead, every witty insult was met with a hearty laugh and a snappy comeback. It was just water off a duck’s back and nothing ever went too far. There was simply no such thing as “too far”.

All because every drag queen in that room never took themselves too seriously. They could gloriously knock themselves down and just laugh about it.

Heal the world.

The most important thing I learnt from performing as Mary May would be that Singaporeans can afford to be more like drag audiences.

Standing on stage in front of a sold-out crowd that night, I couldn’t help but marvel at the amount of support I was shown. Aside from a handful of my colleagues and friends, everyone else was a stranger. Yet all of them cheered with the same enthusiasm.

They sang along and I even spotted nods of appreciation around the room. At the end of the night, the crowd even sang me a birthday song (it was my birthday the next day) with one voice.

Did it matter whether I was straight, gay, or bi? No. All they saw was a guy who had never done anything like this before, try. And I would like to think they respected the effort.

Now would this have been the case 50 years ago? I doubt it. The Singapore we live in today is vastly different from yesteryear. We’ve become a more accepting and tolerant people, yet there’s always room for improvement.  

With section 377A of the penal code once again thrust under the spotlight, many Singaporeans’ archaic attitude towards the unknown and unfamiliar have resurfaced. And it’s pretty ugly.

Perhaps what society lacks then, is understanding. It’s in our best interest to cultivate an environment of support and mutual respect rather than militant, ride-or-die segregation.

After doing drag, I realised that while differences can be intimidating, it’s ultimately nothing to be afraid of.

Beauty is pain. A lot of pain.

To every single lady out there, I am sorry.

I am sorry that both traditional and modern standards of feminine beauty require you to do frankly outrageous things to look “pretty”.

Take makeup for example. Wearing makeup sucks. Wearing drag makeup sucks more.

The sheer number of products needed to exaggerate my features was just staggering. Becca spent close to two-and-a-half hours painting Mary’s face onto mine. But even if painting my face were to only take ten minutes, that’s still ten minutes too long. How does anyone have the patience to do this on a daily basis?!

Also, as I type this, the surface of my legs resemble cacti more than human flesh. A day before the show, I had used an entire tube of hair-removal cream on each of my hairy legs. Those bald chickens have now come home to roost, bringing with them an insufferable itch.

But while the removal of body hair didn’t put me in any physical danger, wearing 6-inch heels definitely did. I’ve actually lost count of the number of times I could’ve broken an ankle while trying to walk in them.

Thankfully, after realising that Bambi on ice would hardly captivate an audience, we scrapped the stilts in favour of the more familiar army combat boots. Decorated with real lace of course.

In other words, I’ve learnt how easy guys have it in terms of looking generally presentable. And never again will I complain about women taking an eternity to get ready for a night out.

Finally, I empathise. Really, I do.


And there you have it: five of my biggest takeaways from doing drag.

Mary May.

Wait, I mean Justin Vanderstraaten.

Want to be a drag queen? Write to us at community@ricemedia.co and we just might hook you up.

Oh, and if you missed the video of me doing drag, check it out here

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