Online Dating: Transgenders Seek Love with Confidence

They say that there’s a match for everyone online, but what about those who don’t fit under the conventional categories? Every straight man can find a woman, every gay man can find another gay man, every woman can find their preference, and every divorcee can find someone who understands what they’re going through. But when it comes to transgender people, do they have the same chance of success as others do online? Not only do they have a place in online dating, they have just as good a chance of finding a successful relationship than anybody else using online dating sites.

“It’s like going to AA meetings,” says online dater and trans-man, Kevin Buckley. “You know there are other alcoholics besides yourself looking for people to relate to, but you rarely bump into them in your everyday life. But then you go to an AA meeting and you’re surrounded by all these people who are doing the same thing you are and are looking for the same support. There are countless transgender people in the world and just as many who would date them, but unless you know where to look, you spend a lot of time feeling alone.”

Many trans-men and women have abandoned conventional (and, let’s be honest, painfully traditional) ways of dating and turned to an online community that isn’t just OK with their gender affiliation, but attracted to it.

Buckley, a 34-year-old who has been living as a man since he was 15, found his fiancee, Debra Wellington, through online dating in 2003, and says he believes he’d still be single if it wasn’t for online dating.

Buckley admits that before meeting his fiancee, he spent a lot of time getting rejected and feeling depressed. “It’s a hard subject to broach, and the stigma attached to it can be a deal breaker for most people. Do you tell the person on the first date, before they get to know you? Or do you wait to see if you want to pursue the relationship further?” In his experience, Kevin found disappointment either way. “You either never get to see where things could go, or you end up getting called a liar for keeping it a secret.” So he went in search of a place where people were actually seeking him out.

“The LGBT community has a great support system, but even still it’s hard to find someone to connect with in a romantic capacity,” Buckley says.

One of the most common problems for the transgender community is the roadblock of not having easy access to knowing who would be interested in a relationship.

“It’s much easier to tell which men will date men, which ones want to date women, which women are straight, which ones are gay—people are pretty forthcoming about these kinds of preferences,” says Sarah Spiers, who has been dating a transgender man named Louis Kendall for three years. “It’s not as simple to know who is open-minded enough to date a transgender person. But with online dating sites, there are full communities of people who are actively looking to be matched with a transgender person.”

Spiers says Louis was surprised at her candor and understanding. “I never had to ask all those particularly sticky questions, because my sister is transgender, and I grew up knowing all about it. I was raised to ignore the overwhelming majority’s discomfiture with the transgendered community.”

The online dating world is often segregated into websites that help you narrow your search. There are dating sites for straights, dating sites for gays, and dating sites for transgenders looking for dates, and people who are looking to date transgenders.

Studies show that one in five relationships for straight couples start online. A staggering number, but these stats don’t necessarily exclude transgenders—many don’t reveal their gender status on the mainstream dating sites until they are messaged privately. For some, being transgender is a deal breaker, and a quick message allows both parties the opportunity to respectfully decline. On those sites that are specific to transgenders and those who are open to them, everyone is up front.

This isn’t to say the online world is void of the negative stereotypes you find offline. “There are people who join the sites just to ridicule you, but they are a very small percentage of the dating pool,” says Kevin, who maintains the positive results make up for any negative encounters along the way. “Those cowardly people need to do that to make themselves feel better—I’m not going to let it get me down.”

The biggest step in a transgender person’s life is making the decision to live in the body they were supposed to be born with. But the second is deciding to let themselves be loved.

Buckley, of course, took the leap and never looked back. “I could finally go on a date and meet someone, and not be completely preoccupied about whether or not I should tell them about my past, it was the most freeing experience.”

It seems there is not only space for transgenders in the world of online dating, but it may certainly be the safest way for transgender couples to find each other without fear of societal persecution. At least until acceptance and understanding makes its way into mainstream norms—a feat that we come closer to every day.

Jesse Woods is a resident Sexpert at’s Adult Personals blog. A writing major from NYU, Jesse is currently completing a second degree in Gender Studies.

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