Saskatchewan·In Your Shoes

From drab to fab to drag: Extreme makeover a lesson in acceptance

For someone who doesn't often wear makeup, the things laid out on this table look like instruments of torture. A multitude of unfamiliar sticks, colours, fake eyelashes and glue flash before me over the course of a two-hour transformation into a drag queen.

No better way to experience Regina Pride than jumping fully into drag queen makeup

Among this week's Pride events was a Drag Queen 101 class, teaching the basics of makeup and contouring, and for those willing to give it a try, the full drag queen makeup experience. (The Associated Press)

For someone who doesn't often wear makeup, the things laid out on this table look like instruments of torture. A multitude of unfamiliar sticks, colours, fake eyelashes and glue flash before me over the course of a two-hour transformation into a drag queen.

I've never felt very comfortable applying makeup. The few times I've tried, I feel like I end up looking more Marilyn Manson than Marilyn Monroe.

So when a friend suggested trying Drag Queen 101, a lesson on contouring and makeup offered during Regina's Pride Week, I thought, "Why not?"

Why not try something new and completely different? And what better time than during Pride? 

That's how I ended up sitting at this table with drag queen Yada Ya-Oughtta-Book-Ahead, known in her alternate life as 54-year-old Gerrard Dillman, makeup master and owner of enough product to make Kim Kardashian spontaneously burst into flames of envy.

The initial makeup selections on the table are dismissed by drag queen Yada, who pulls out her personal and much more extensive selection of MAC makeup. (CBC News)

Yada confesses to being a little nervous about doing someone else's makeup, but agrees to give it a go.

"Sometimes it's just a super kick to do somebody else for a change rather than my old mug in the mirror," he says, laughing.

First, he and a fellow makeup artist glue my eyebrows down and completely disguise them with foundation.

A makeover as a drag queen starts by getting rid of eyebrows. (CBC News)

Then with a feather touch, his breath gentle against my face, Yada applies layer after layer of makeup, explaining as he goes along how the bright white streaks will make my face shrink, or how dark lines will emphasize my smile and lips.

It seems bizarre, but every so often I look in the mirror. I'm amazed by the transformation.

"Holy crow, my skin looks fabulous!" I cry. I look again later and say, "Wow, I have cheekbones!"

Yada/Gerard said they had never done drag makeup for someone else before. (CBC News)

I wear fake eyelashes for the first time ever, leaving me feeling like Bambi peering out from the thick, black, unfamiliar weight.

Then Yada sprays my face with hairspray to hold it all together. She suggests the final touch, a vivid orange wig that offers a spectacular contrast to my brown skin.

I gawk at the final product, the stranger in front of me. It's hard to believe that my makeup artist undergoes this transformation so regularly, turning his face into a canvas that sees him sliding between the personalities of Gerrard and Yada.

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The makeup releases something in Yada, a freedom to be more bold and sassy, to crack jokes and order strangers to buy her a round of shots.

"It totally creates a character for me. And people love that character. They sometimes forget that there's actually a person behind the makeup," she says.  

Yada Ya-Oughtta-Book-Ahead has a confidence and quick wit that her alter ego Gerrard Dillman sometimes envies. (Submitted photo)

Somehow, the makeup's mix of chemicals releases a confidence and security that Yada can't help wondering about.

"It's odd that it does that, and it's frustrating sometimes that it does that, and that we can't sometimes just grab a hold of that portion when we're out of it as well," she says.

I understand exactly what she means, that sense of uncorking liquid confidence and femininity from a bottle.  

Yada Ya-Oughtta-Book-Ahead, also known as Gerard Dillman, poses for a picture with the subject of his makeover. (CBC News)

When I walk through the doors at home, my children don't recognize the new me. My youngest lets out a high-pitch squeal whenever she sees my face, and covers her eyes. When I scowl at her later for misbehaving, it has an immediate effect of stopping her in her tracks, as she squeals and cowers again.

I've unexpectedly stumbled on a good disciplinary tactic — 'Be good or I'll put makeup on!'

As fun as it is to strike terror into my child's heart, eventually I go to wash my face.

I look at the mirror one last time. Most of us have features we'd change if we could, maybe physical ones like an oversized nose or a receding hairline, or emotional ones, of anxiety or insecurity.

But as I keep staring, I don't see or feel these flaws. For a moment, I feel like I'm looking at two mirrors creating infinite reflections of myself.

I realize there's so many ways of seeing yourself and the world around you beyond the flaws, beyond black and white or even shades of grey. And I realize how richer the world is when you look through that lens of acceptance, like the multi-coloured variance of a MAC colour palette with all the brilliance and vibrancy of a Pride rainbow.

CBC Saskatchewan's weekend team is heading out of the newsroom (and their comfort zones) this summer for our In Your Shoes series. Reporters will be trying a range of activities in Saskatchewan and reporting back. They will be taking nominations and suggestions from readers, so let us know what you want to read about next. Email with your ideas!


Janani Whitfield works on CBC Saskatchewan's Morning Edition. Contact her at or on Twitter, @WhitfieldJanani.