Things You’re Too Afraid To Ask A Singaporean Trans Person


If you’ve stumbled across posts on Reddit, you likely know what a subreddit is. Subreddits are little communities or forums within Reddit that have a spectrum of topics. You’ll find subreddits that are about film and also subreddits that are about cats looking like loaves

Amongst these, there’s one called r/TooAfraidToAsk where well-meaning Reddit users have their questions (that would typically be deemed offensive) answered. This subreddit is often littered with questions relating to sexuality and gender perception; no surprise, given that these topics are often personal in nature. 

An image of a question from r/TooAfraidToAsk about trans people.
Read users’ answers on the Reddit thread.

In this article, I’m sharing my engagement with Sherry, a transgender individual in Singapore, a country where topics of sexuality are subject to constant debate. Within the LGBT+ community, trans individuals are arguably the people most shrouded in mystery. 

This is an article for you if you’re curious and TooAfraidToAsk. You may fear to ask these questions because they’re objectifying, or maybe because you don’t know enough trans people. Being too afraid to ask is a good thing.

But that doesn’t mean you shouldn’t have your questions answered, because a lack of knowledge is sometimes what contributes to discriminating objectification. Maybe you’ve got excuses, and I get it: life is a tiresome drag. Here’s a cheat sheet of sorts:

Image describing how stressed people make ideal workers but distracted citizens, where citizens are too pressed making a living to contribute to social issues.
Before writing this article, I ran an Instagram poll about questions my minimal following would like to ask a trans individual. 

Some of these questions are shallow, dehumanising and stereotypical. I’m actively apologetic that I had to ask Sherry these, but they also serve the purpose of clearing minor misconceptions so we can all start to focus on and fight for issues that actually matter.

Some of these are also questions that will incite different answers, depending on who you ask. 

Here goes nothing. 

Meet Sherry

Sherry Sherqueshaa’s a 28-year-old Muslim transgender woman (to clarify, she was born a biological male and is now female).

Sherry, photographed by Leslie Kee for Out in Singapore. Source.
Sherry, photographed by Leslie Kee for Out in Singapore. Source.

Sherry is a researcher and writer with Project X, an organisation in Singapore that focuses on outreach to support sex workers in Singapore.

I know what some of you are thinking: “So, is Sherry completely a female?”

You may want to rethink pinning someone’s identity to their sexual organs – but back to the point of this article. I asked Sherry about where she was in her transformation.

Trans women awareness. More than meets the eyes.
Comic by Julie Kaye. Source.

“Stage of transformation? For trans women, it is breast augmentation and gender reassignment. I have done my breast augmentation and have no plans for gender reassignment.”

Sherry is still a woman. Sherry started feeling like a woman back in her teens, though she only learnt about the term ‘transgender’ when she was in her 20s. 

Did you experience gender dysphoria?

Gender dysphoria refers to the emotional and psychological distress or unease that an individual feels with regards to their physical gender and the gender that they identify it with.

Picture it to be like a specific type of existential crisis (but far less pretentious).  

An image accompanying an article titled "You Can Still Be Transgender If You Don’t Feel Physical Dysphoria – Here’s Why". Source.
An image accompanying an article titled “You Can Still Be Transgender If You Don’t Feel Physical Dysphoria – Here’s Why”. Source.

Sherry says yes, and no. Sherry found her dysphoria to be normal.

“I didn’t confide in anyone about my feelings and needs.”

Transitioning: Was There a Beginning and End?

Sherry began her transition with fluidity when she stopped exemplifying the actions of her male cousins or friends, whom she couldn’t relate to anyway.

Instead, she chatted girls up in a different way, becoming fond of them rather than looking to court them. 

She gradually progressed with makeup, attire, and then living as a woman. 

How Do You Feel Looking At Yourself In The Mirror? 

When it comes to the question of changing looks and modified features, many say that they’d never do it simply because they’re afraid their personal familiarity will never quite make an exception for their physicality.

For Sherry, transitioning just helped put both aspects together. 

Sherry looking stunning in a mirror selfie.
Sherry looking stunning in a mirror selfie. Sweet christmas!

In fact, there’s an expression that she chose to describe how she feels when she does, and it’s “sweet christmas!”

“Every time I look at myself in the mirror I feel so satisfied. From the infancy stage until now, I was proud of the changes, whether small or big. The more I look at myself in the mirror, the more I become very confident and empowered.”

When Did Sherry Start Using Female Toilets?

This was a very recurring question that I got from the people that I interacted with when collating questions.

I believe this is to ask Sherry and other trans people when did they start abiding by societal gender classifying standards, a materialisation of the gender checkboxes in forms.


“I don’t remember at which stage or age I started using the female toilet and affirming my preferred gender. 

All I can remember was that I’m very shameless and proud of myself despite actually not being passable at the beginning of transition. 

I only got pissed when others purposely misgendered me or shamed me in front of others.”

Misgendering and Shaming? Does That Actually Happen?

While that’s something you may never resort to, there are those who think it’s okay to shove their notions down others’ throats in abusive manners.

Sherry has dealt with it in ways that have changed over time. 

Posters at the University of West England in Bristol. Source.
Posters at the University of West England in Bristol. Source.

She’s quick to clarify that discrimination and frequency are subjective things. Sherry has had to deal with discrimination socially, professionally, and in relationships.

“Trans folk have it worse,” she tells me. 

Contrary to what many (myself included) may think, Sherry seems to see living in Singapore as a semi-positive thing. 

“We are not led by a single faith or beliefs. We move along firstly by civil laws. Though they can be more helpful to the marginalized community, as of now, the law somehow protects everyone.”

How Do You Deal With It?

In the infancy stages of her transition, Sherry was constantly on the lookout for other people staring, whispering and laughing. She’d react by giving them a piece of their own medicine, scolding them and sometimes even shouting. 

She has now resigned to a more passive approach because her former approach is “actually tiring and pointless”.

Her friends and family seem to have struggles dealing with it more than she does because they haven’t been able to cope the same way. 

“I still remember when someone related to me stood up for me in public. He was pissed that passersby kept looking at me. He felt that our personal space had been intruded.”

For Sherry, moments where friends and family stood up for her have empowered her and helped her come to terms with who she really is. 

How Can I, A Cis Person, Be A Good Friend To A Trans Person?

If you’re cisgendered, it means that your sense of personal gender identity corresponds to that of your birth sex. 

Sherry says the best way to be a good cis friend is to be a normal, good, human being who sees your trans friend as just the same. This means being genuine and unintrusive.

“I mean, it’s a common trait in any friendship.”

Friends help friends.
Friends help friends. Source.

Beyond that, Sherry tells me that being a good cis friend means accepting the baggage that comes with being friends with a trans person.

With how stigmatised trans individuals are in society, it sounds like no mean feat, and according to Sherry, part of it involves “being questioned on why you’re friends with a trans person, being stared at in public, etc”. 

“I get attention – good and bad – when I’m in public, so those who with me they may have to bear with me being approached, being stared at, and much more”.

What About Family? 

This is likely something that varies based on every individual. I mean, we’ve all had that friend whose folks drank alcohol with them during their teen years.

We’ve also all had that friend whom you’ve never seen at class chalets and after-school outings. Maybe you’re one of those friends. Point is, to each friend, their own set of folks. 

And as far as Sherry’s folks go, they’re now always plugging her from the sidelines of her achievements, like attending her beauty pageants (which she has won, by the way). 

“Imagine this: from having a son to a daughter who’s now competing in a beauty pageant? Having their support is already a win for me.”

Sherry in a video by The Straits Times. Source.
Sherry in a video by The Straits Times. Source.

Do Your Dates Know?

Trans women are VERY commonly fetishised, and the psychological reasoning for this is something you can go look up on your own if you’re interested. 

I understand when Sherry tells me that she chooses not to reveal that she’s trans at the very beginning of a romantic relationship. Oftentimes, it has changed the intentions of many when speaking with her. 

“Most will not take me out for a date but only for sex or they won’t be interested at all.”

Angel and Stan from Pose on FX discuss Stan's attraction to Angel because of intense objectification. Source.
In an emotional moment, Angel and Stan from Pose on FX discuss Stan’s attraction to Angel because of intense objectification. Source.

In Sherry’s time dating and using Tinder, she has typically only disclosed her identity in the event of suspicion or when the pre-planned occassion is sex, rather than a date. Sherry finds that this helps her keep conversations more casual and realistic. 

If you’re wondering how Sherry feels during sex after transitioning, she says she feels far more comfortable now than she did before.

It’s Honestly So Tough. Why Don’t You Just…Pass?

In the trans world, “passing” is a term that refers to an individual’s ability to be perceived as the gender that they identify with. After you’re “passable”, choosing to publicly identify as trans is an additional active choice.

By choosing to make this addition, trans people are practically subjecting themselves to additional negative repercussions from society. 

I ask Sherry if she ever feels like just passing as opposed to being an activist. Her initial answer is “no”. Discrimination only empowers her desire to own her identity. 

Sherry shines with confidence in a selfie.
Sherry shines with confidence in a selfie.

On second thought, she tells me there was once a part of her that wished she could pass, though her reasons are very personal. 

“..Because of my family and friends. They don’t really understand the world of discrimination and transgenderism, and I hate myself for putting them in the limelight. Relatives question them about my decision, and people don’t know how to respect us. I’m known for my success and recognition. Leave my family alone. This is why I wished I could be passable.”

Comic by Julie Kaye. Source.

In Sherry’s world, where discrimination makes living a struggle, it terrifies me to think that those closest to you might have to be shunned just so they aren’t put through your pain.

So What Makes It All Worth It?

“What makes it all worth is that I know I rely on no one to stand up for me.

I stood for myself first before expecting others to do so. From being a sex worker to an activist, each milestone has made it worthwhile.”

Sherry’s confidence in her sense of individuality is something that many of us (myself included) can only dream of achieving.

Being a Muslim, Sherry weathers on as a mouthpiece for a community that is silenced in ways she isn’t. It is for reasons like this that she embraces her identity fully.

Art by Julie Kaye. Source.
Comic by Julie Kaye. Source.

Understanding of this topic can never be demarcated by the reading or writing of an article. We’ll never actually understand until we’re in the very shoes of a trans person. The best that we can do is to be supportive, to stamp on discrimination, and to stay educated. 

If there’s something tangible that your friends or you wonder about trans individuals, don’t let these grow into toxic slivers of doubt. Don’t let these become the slivers that lead to you objectifying a trans person and discounting their humanity. 

Sherry is a brave, sparkling firework of a human, as many others are, and as we can all try to be.

“Being trans is like a living gallery of Grammys. We work hard for all that others see us – courage, confidence, looks, passion, and you complete the list.”