How I Found My Place as a Female, Part 2: The Dichotomy Between Masculinity and Femininity

This is part 2 of my 3-part series on my struggles finding my identity as a female and how I found my place as a female in today’s world. If you are new here, read Part 1: Growing Up with a Repressed Femininity first.

Girl behind leaves

18 was the start of many changes. One, it marked my graduation from traditional, classroom-style learning and matriculation into tertiary education. Two, it was the start of adulthood, where I began gaining autonomy over various areas of my life. My gender identity was one of them.


Evolving in My Appearance

Up until I was 18, I had been blindly following my mom in terms of how I should conduct myself as a female. Since my mom is somewhat androgynous, I grew into quite an androgynous girl. It was only when I was 18 when I started thinking about how I wanted to look, speak, or act as a female.

Reaching 18 and entering university made me more conscious about increasing my feminine appeal. After all, university is a time when you meet an influx of people–including people of the opposite sex. Like other teens, I wanted to appeal to the opposite gender and perhaps meet the guy of my dreams. (Apparently I did meet him (Ken) when I was in university, but it was only ten years later (this year) when we got together and became engaged.)

Since physical appearance is the most visible part of a person, I began working on my looks first, starting with my hair.


Having been forced into a short hairstyle when I was a kid, I became accustomed to having short hair. Coupled with the fact that my mom would bitch at me whenever she saw my hair growing longer, I would get my hair cut short very often. My hair never grew beyond my neck.

Then when I was 18, suddenly I realized that I can have long hair if I want to. Even if my mom is to insist that I have short hair, my hair is mine. It’s up to me to decide how long it should be.

So even as my mom repeatedly insulted my hair as I grew it out, I ignored her and grew it beyond my shoulders. (I never had short hair since then, except once when I was 25 and wanted a change in my look.)

A girl's back view



Dressing was the next thing I worked on.

As I mentioned in part one, I had friends in junior college who were highly image-conscious. One of them often read beauty magazines, checked out makeup when we walked past drug stores, and shopped for clothes. These friends got me thinking about how I should be more fashion-conscious too.

Shopping became a personal pastime. I would shop on a once-to-twice weekly basis, each time looking for clothes that would make me look good. Gone were the old, unisex clothes I had as a child; in were the nice and fashionable clothes which complemented my body. Whenever my clothes stopped looking good on me or went out of trend, I would throw them out and switch to a new wardrobe. Looking my best was a priority over conservation.


I also began putting on makeup–something which I wish I looked into earlier. For makeup was great for concealing my pimples which I had many of when I was in JC and university (the large and painful ones too). Not only that, makeup also improved my complexion and enhanced my looks.

Hence, makeup became part of my daily routine. As I grew older, I became better at using makeup to enhance my natural looks and look more attractive to the opposite sex.

Becoming Prettier; Yet Continuing To Feel Unfeminine

With these changes, I easily became prettier and more feminine. Guys began to pay attention to me; pickup attempts off the street, restaurant, or even bus were not uncommon. People–friends and relatives alike–often dropped compliments about my looks.

So it seemed my efforts had paid off. I worked on my hair, dressing, and makeup to increase my feminine appeal and it worked. I should rightfully be happy.

However, I wasn’t. Despite now looking prettier and more feminine, I continued to feel unfeminine as a woman.


One of the reasons was because I felt that I didn’t look pretty enough. The media constantly projects an ideal image of beauty. In my country (Singapore), this ideal image of beauty consists of large eyes, a small and sharp face, thin legs, a flat tummy, snowy complexion, pearly-white teeth, and so on. While I knew that I looked good–even pretty, I felt that I didn’t look good enough and couldn’t be recognized as a female until I achieved that ideal image of beauty.

Hence, I kept working on improving my looks.

Another, bigger, reason was my character.

A girl's back view, at the field

Breaking Down My Character: Dichotomy Between Masculine and Feminine Traits

For a long time, I felt like a masculine woman. That’s partly because I possess traits like drivenness, decisiveness, resilience, sharpness, outspokenness, persistence, and boldness–all of which are often regarded as male-traits.

Another reason is because I tend to supersede guys around me in terms of personal achievements and capability, which I’ve covered before in: Why I Used to Be Afraid of Intimidating Men and Why It Does Not Faze Me Anymore.

It wasn’t that I didn’t want to be soft, dainty, and demure. The issue was that firstly, I live in a meritocratic society like Singapore, where achievements form the centerpiece to one’s worth, and secondly, I’m passionate about personal growth. In order to excel in life and be the best one can be, one has to embody power traits like the above, which was exactly what I did. 


For what it’s worth, these traits served me well. I would achieve one goal after another, from being the top student in my area of study, to landing a coveted job in a Fortune 100 MNC, to excelling in my job, to setting up my blog/business, to achieving high traffic in a short amount of time, to turning my blog into a passive income machine, to being continually featured in the media. Without them, I would not even be half the person I am today.

However, these traits ran counter to feminine traits I wanted to build, such as softness, daintiness, and demureness. For example, being resilient is odds with being soft. Being swift and decisive run opposite to being dainty. Being outspoken and assertive do not exactly sync with demureness.

So I would flick back and forth between striving for my goals and being feminine. Whenever I strove for my goals, I would be my natural self, but I would feel upset for not being feminine enough. Whenever I tried to be feminine, I would feel good for not coming on too strong onto others, but I would sad for having to repress my real personality. I felt like a spring pulled and stretched to meet two ends.

Fruitless Attempts to Resolve the Conflict, Be it via Character or Appearance

While I was attempting to meet my contrasting desires of success and femininity with limited success, I was simultaneously increasing my femininity through my appearance. I would doll myself up further, wear nicer and more fashionable clothes, and put on trendier accessories. This probably helped spark continual male attention; I also continued to receive compliments from people about being cute/attractive.

The funny thing was that I disliked receiving male attention (which I wasn’t looking for). There were two reasons.

Firstly, my mom*–through my childhood experiences which I shared in part one–made me subconsciously feel that I would be a slut if guys were attracted to me, even if I did not solicit for the attention. Hence, attracting attention from them–especially lewd attention like guys whistling at me from their cars, neighborhood or coffee shop uncles trying to hit on me, or even molestation encounters–would made me feel grossed out (at myself), like I was a whore.

— Insert side note —


I just want to make a quick note that while some of my childhood encounters with my mom caused my femininity to be repressed as a child, this was by no means her fault; neither was/is there anything wrong with her. Many of her beliefs (which gave rise to those encounters I shared in part one) are very, very common among people from older Asian generation. If anything, I see this as an issue with the Chinese culture and some of its beliefs — which are fundamentally backward, misogynistic, and dehumanizing in many ways (for example, corporal punishment and death penalty are accepted in the Chinese culture). Many traditional Asian parents have much more backward and female-repressing views than my mom. I personally am thankful to have her as my mom and that she did the best she could, within her circumstances.

At the end of the day, whatever experiences I had as a child have helped me learn and be who I am today. There’s nothing wrong with my mom and I don’t wish for this series to cast her in a negative light in any way, because she is a great woman and she has raised me in the most beautiful way she possibly can. After all, if I had a different set of parents, I’m not sure if PE would have existed today? 🙂 I respect and love her for raising me and I hope all of you will think the same way about her as well. Thanks! 🙂

— End abrupt side note —

Secondly, I didn’t want a guy to like me based on my appearance alone, even though I would always be flattered by that. I wanted guys to be interested in me for the finer aspects of my personality, such as my intellect, resilience, and drive. I had been on dates before where the guy’s interest was driven by superficial things such as age compatibility, my looks, and so on, and the dates were always empty; hollow (because there were no deeper areas of compatibility to build a connection on). They were always a waste of my time (and also the guy’s time) because it was impossible for us to build any meaningful type of relationship together.

So imagine the ironic situation I was trapped in where (a) I wanted to be feminine as a person but couldn’t because my passion for growth and success kept leading me to traits which are more masculine, and (b) increasing my femininity through my looks led me to loathe myself because I felt like I was being some kind of slut for attracting unwanted male attention.

It seemed that I couldn’t win no matter what I tried to do. It seemed that I was stuck with my developed masculine self with nowhere else to go.

Sad girl at window

Conflicted about Who/What I Should Be as a Female

Thus, for a long time, I was confused about who/what I was supposed to be/do as a female.

On one hand, I was expected to be the best that I could be and to achieve my goals with excellence. To do so would require me to cultivate male-associated traits like drivenness, ambition, self-assuredness, and so on.

On the other hand, I felt that I needed to be submissive, tame, quiet, reserved, conforming, unassertive, etc. to be recognized as a feminine female. This is especially so in the at-times-non-liberal Asian culture.

What am I supposed to do? Who am I supposed to be? were statements I kept asking myself. I had no idea who or what I was supposed to be as a female in today’s world. I had no idea what exactly society was expecting of me to be as a girl, a woman, a lady. I felt I was trying so hard to fit in but I was unable to.

It was later in my late 20s that I came into my own and found my foot as a female. Much of it has to do with my revelations surrounding beauty, men, and my body.

Read part three, where I share how I came to realize my place as a female: Part 3: Coming Into My Own as a Woman

This is part 2 of my 3-part series on my struggles finding my identity as a female and how I found my place as a female in today’s world. If you are new here, read Part 1: Growing Up with a Repressed Femininity first.

Images: Girl behind leaves, Girl with long hair, Girl’s back viewSad girl at window 

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