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Transgender Dating Online

Dating is difficult enough when you fit into society’s most basic sexual conventions; when you’re gay or straight, lesbian or bisexual. In fact, it’s difficult at best. Many hate the process of misses and hits, repeated efforts, making the same mistakes and meeting the same people over and over again. It can seem utterly hopeless, and never-ending.

But if you self-identify as transgendered, as an out transgendered male or female, as transitioning, or simply identify as a gender different from the one assigned by the conventions of your birth and childhood, dating can present more and very different challenges.

Away from online dating, in the real world of blind dates, friends-of-friends, dating services, and singles’ events, the elephant in the room being invisible doesn’t help: at least online, everything is out there in clear terms, and anyone pursuing a transgendered person’s dating profile has already made a decision about those terms.

Online Dating for the Transgendered

With online dating, a significant part of the problem is the lack of mainstream dating sites that cater to–or are even prepared to serve–transgendered people. The transgendered will feel marginalized by most mainstream dating sites: few categorize for transgendered dating as they do for straight, gay, and lesbian; and fewer still offer gender identifiers beyond the binary Male and Female. And those dating services that do cater to the transgendered are as marginal as the transgendered are underserved. Many transgendered people enter the dating world identifying as gay or lesbian, even if they are seeking the opposite of the gender with which they identify. Some identify themselves as transgendered in their dating profiles; some do not.

To Disclose or not to Disclose

Many transgendered people who are actively dating believe it’s better to wait for a meaningful connection with a potential partner before disclosing that they are transgendered. Others believe it should be disclosed right away.

Potential partners of transgendered people can be misinformed, or uninformed: the mainstreaming of transgender issues is practically brand-new in our culture, and there is very little reliable information making its way to where anyone but the most socially concerned can find it. The transgendered always risk being accused of dishonesty; they risk facing confusion about their anatomy; they risk simple homophobic ignorance from those with whom they have not disclosed that they are transgendered. From those with whom they have disclosed that they are transgendered, they risk distraction, being treated as a novelty, and a ceaseless struggle to secure validity as their gender.

Fine, In Theory

The west has taken great strides in accepting and extending rights to the diverse range of gender and sexual identities. There’s no doubt about that. And though the steps that have been taken cannot be dismissed, it also cannot be overlooked that there are many more steps to be taken: Nearly any transgendered person who has ventured into the dating game is aware of that. People sometimes consider themselves a great deal more open-minded, more culturally adjusted, than they actually are. The transgendered person who has struggled with dating will tell you about last-minute cancellations from apparently “comfortable” potential partners; about sexual cold feet; about awkwardness, about marginalization. Even among some of the most progressive potential partners there is a comfort gap when it comes to the transgendered: they are fine with it, in theory; in practice, they can feel very differently.

Social Media

A potential course for the transgendered who are struggling to date is social media. Sites like Facebook represent opportunities to convene in online groups, even geographically, among like-minded, truly accepting, or transgendered users. Twitter and Instagram represent filter-friendly ways to connect; Reddit has a number of transgender-friendly subreddits, including one just for transgender dating and another popular one at r/asktransgender. Social media sites like these can be used to make new connections, develop them, and ultimately to arrange meetings in the real world.


Dating is difficult for almost everyone seeking love, or at least a meaningful, sustained connection (or series of connections) with the potential to turn into something greater. It is even more difficult for the transgendered, who must validate, defend, and even prove elements of their identities before, while, or after meeting a potential partner.

The same things that can encourage and inform the straight, gay, lesbian, and bisexual people in the dating world can inform the transgendered: make a home for yourself in your body; make decisions that reinforce your identity rather than expose it to scrutiny; and don’t lose hope. Everyone struggles to find the right one; but that means the right one is out there struggling to find us.

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