The term "Paradox of Privacy" usually refers to the disjoint between expressed privacy concerns and actual online behaviour. We bemoan about how big tech companies like Facebook and Google harvest our personal data and insidiously selling it to advertisers, yet we still willingly let them do so in exchange for convenience (google maps) and desire to show off our lives to the rest of our friends (sharing of photos/videos on Instagram and facebook).

I think crossdressers also suffer from their own paradox of privacy, albeit different from what I just described. We express privacy concerns and worry about the impact should our crossdressing inclinations be made known to our partners, relatives, friends and colleagues, yet we keep wanting to show our female selves to people, be it on Facebook, Instagram, Reddit, private chat groups, etc. This paradox is only faced by crossdressers who have not yet come out fully to the rest of the world (which is a lot of us in Singapore).

The crossdressers' paradox of privacy stems from the deep desire to accepted by others, to be told that you are beautiful/pretty/successful as a woman. Although the desire to be praised in this age of social media applies to everyone, for crossdressers the desire runs a lot stronger because acceptance is less easily available. Family and friends may not be understanding, while mainstream society has a tendency to brand a crossdresser a deviant (Crossdressers generally are viewed as perverts who get off from wearing women's clothes. It is really difficult for a crossdresser to explain that he likes to wear women's clothes because it makes him feel sexy or turns him on. A good parallel would be people who are into BDSM). Because acceptance and praise is in limited amount from a crossdressers' immediate circle, he turns to social media for likes/comments/praise. The way we "show-off" is also very narrow; usually it is a photo of ourselves dressed in out latest purchase, asking on social media if we are pretty or outright stating that we are. I am guilty of that measuring my success as a crossdresser by this same narcissistic metric.

Isabelle has social media accounts which a restricted group of crossdresser friends has access to. At times I think to myself: Why am I being so scared? I've taken so much effort to level up my skills to look sufficiently convincing as a girl, shouldn't I just make my accounts public or post my photos on more public platforms like reddit? This way I could be admired more, feel a sense of success, drive more viewers to my blog. But then my risk-reward alarm bells go off and my guy self slaps sense into Isabelle, reminding that such "recognition" that I seek on social media is ultimately meaningless and will not solve the deep rooted self-esteem and gender dysphoria issues that I face. And in exchange I flippantly squander away my privacy.