In an effort to build confidence, the writer tried on makeup. Here's what he learned.

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I wonder if everyone at this bar thinks I look like a geisha — a dude geisha. Are the other patrons sneaking glances at me, judging the guy alone in a booth? I’ve come prepared for a date, dressed in the standard-issue San Francisco uniform: dark jeans, desert boots, crisp button-down.

I’ve also added the sheen of makeup on my face.

The girl I’m meeting is late. Her online profile was funny, and she’s much cuter than me, which makes me nervous. I need to be confident, charming and witty. I need to impress her. The makeup begins to feel unnatural, like a plastic film over my pores. They aren’t used to a layer between them and the outside world, and I start to itch. I scratch the side of my face.

Is there now going to be a line on the side of my face? Also how does this foundation look in this dim lighting? To my date, will I resemble a 9-year-old girl who got a hold of her mother’s makeup kit, or a responsible 29-year-old man who pays rent and appreciates rye whiskey? I weigh the benefits of verifying that I look fabulous by whipping out my cellphone camera, but what if my date walks in and sees me doing so?

I begin to regret this self-inflicted stress, but then I take a deep breath and remind myself why I decided to put on makeup in the first place.

Making a decision

The author is ready to face the world with foundation and BB cream applied. (Photo courtesy Benjamin Yu)
The author is ready to face the world with foundation and BB cream applied. (Photo courtesy Benjamin Yu)

It all started with the fact that I am not an attractive man. I’m not fishing for pity here. Sometimes you have to accept that you didn’t win a particular life category. The biggest flaw is the acne that popped up to say hello in middle school and then made permanent residence on my face, despite the efforts of dermatologists, antibiotics, Accutane and expensive skin-care products. A decade-plus of acne has left scars that I tell myself build character. I don’t let them stop me from being happy. I have a good job in marketing. My personality is fine; I have decent social skills. I even found someone who loved me for who I was. Until she didn’t.

Feeling inadequate is a common side effect of being dumped. Newly single, every morning in front of the mirror was a battle for self-esteem. I saw only the things I disliked about myself. It would start with any new zits on my face and bleed into feelings about other parts, such as my hair (I look like a Chia pet!) and facial structure (one eye looks asleep and the other like it saw a ghost). One morning, this battle escalated into an all-out war. I was going to do something about feeling this way. I swallowed my burly man pride and went nuclear. I decided to wear makeup.

Entering the makeup world

“You really should go to Sephora and try some swatches,” a female friend said when I told her my plan.

I imagined going into the store and asking some teenage girl working a summer job for help. Just the thought filled me with shame. I debated what was worse: a doting and sympathetic “aww” or a silent judgmental look. It was too much.

The internet wasn’t much help. I did learn that I’m not the first straight man to experiment with makeup; several news outlets have written about the trend. But 14-minute YouTube videos on how to apply makeup are like watching a foreign-language movie with no subtitles. The most popular videos and message boards are filled with advanced topics. Masters of their craft discuss undertones, compare brand shades and consider what products to mix together to form the perfect blend. I just wanted to know the difference between foundation and foundation primer; whether I needed to buy a brush (also, are there different brush types?); and whether I’d like matte finishes in makeup if I liked them on cars.

It was overwhelming. But feeling ugly is a great motivator. I spent more than $100 on BB creams, foundation and concealer. I picked Asian brands with the logic that these products should work well for me since I, too, am Asian.

At-home practice

When the makeup came in, I smuggled the products into my bathroom, locked the door and made up for a lifetime of not taking bathroom selfies. The photos were clinical, to evaluate before and after applications from multiple angles. If my face ever becomes disfigured in an accident, my doctors will have ample reference material for my facial reconstruction.

Mistakes were made in the process. I learned that, unlike sunscreen, makeup can’t be applied haphazardly. It gets crusty and stuck in hair. It requires the skill of “coloring inside the lines.” Applying makeup can also require eyes to readjust, like they do when you step into the sunlight. At first, I thought I looked pale and dehydrated, as if I were recovering from food poisoning. It wasn’t until closing my eyes and opening them again that my skin looked natural. At the end of my experiments, for the first time, I looked at myself, smiled, and thought: “I look good.”

Then I noticed the bags under my eyes and thought about buying eye cream.

Taking it to the streets

Before my first foray out in public, I had to prepare. I took selfies in different lighting conditions: in the bedroom, in the kitchen, next to a floor lamp, outside in direct sunlight and outside in the shadows. I worried my co-workers would notice, and so I came to work ready to claim that I was doing it out of curiosity. I prepared myself to laugh and brush off comments and practiced philosophical arguments on the relationship between masculinity and vulnerability.

As I walked into a Monday morning meeting, though my heart pounded, I tried my best to appear casual. I braced myself for the questions and strange glances. Instead, my co-workers proceeded in a banal fashion: good mornings, questions on everyone’s weekends, and an awkward transition into project updates. No one mentioned my face. Nobody sent me clandestine messages about it afterward. Nobody noticed. No one cared.

I put on makeup every day now. That “I look good” feeling every morning is a much better way to start a day than trying to run away from the mirror. Makeup helps me stand a bit straighter and be a bit more bold. Makeup helps me think about the things I have (a sense of humor, slender build, a passionate heart and analytical mind) instead of the things I lack.

Back at the bar, I whip out my phone to check and see how my makeup looks before my date arrives. How could these bar patrons notice, if my co-workers don’t? Why does it matter if I were to say, “I was just checking my makeup” to a date? It certainly makes for much better conversation than generic icebreakers about our work, food or childhood homes. There’s no reason to be afraid. I’m not wearing it for her. I’m wearing it for me.