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It could be your prototypical 21st-century love story. Boy meets girl on an online dating site. Boy loves girl. Girl loves boy. And after realizing that they can't live without each other, boy and girl get engaged.

But there is one small catch; the boy was born a girl.

Rebecca, a 34-year-old administrative assistant, immediately knew that Alex (not their real names) was different from other guys she'd dated. But it wasn't until the 32-year-old teacher nervously disclosed the truth over a drink that Rebecca fully understood the extent of that difference.

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The world of online dating is fraught with judgments, biases and dead ends. It's difficult terrain for many people, who often feel it's like an exercise in marketing. To cast themselves in a favourable light, some online daters get professional photos done; others fudge about their height, weight or age. They may also withhold details that could drastically limit their chances.

But for transgender individuals – those who have physically, mentally and/or emotionally made a transition from their born gender into the opposite gender or gender role – the online dating world is a minefield. The question of how much to disclose in one's profile is a difficult one.

The inclusion of Chaz Bono as the first transgender contestant on Dancing With The Stars has brought transgender people into the spotlight of popular culture on a more human level than ever before. But mention Chaz's impending nuptials to partner Jennifer Elia, and eyebrows are raised. The sexuality of transgender people continues to be met with confusion, and their dating lives are rarely discussed.

"With few exceptions, people don't go to a dating site looking for a transperson," Alex says. "And most transpeople who aren't out wouldn't want to date someone who is openly looking to date a transperson."

There are also issues relating to sex and the need for medical intervention if pregnancy is something the couple wishes to explore down the road.

Some transgender people report that their online profiles have been deleted; they wonder if their gender identity played a role.

According to Markus Frind, CEO of popular online dating site Plenty of Fish, this is simply not the case. "There is no policy," Mr. Frind writes in an e-mail. "To give you an idea of scale, we'd need to hire close to 2,000 employees if we wanted to moderate/review users' profiles."

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But that does not mean that transgender people are not discriminated against by potential suitors.

For Angie McAvoy, who is at the beginning of a transition from male to female, honesty is the best policy. Still called Andy by most friends and family members, and undaunted by pronoun slips, Angie says she has always been extremely upfront about her impending transition when communicating to potential love interests on the Internet.

"I'm pretty much open," she says. "I think that's the best way to go about it."

Ms. McAvoy is currently seeing a woman she met on Craigslist, and believes that transgender people should be as frank as they are comfortable with in their online profiles, though she concedes this puts them at a disadvantage. For one thing, there are only ever two options for gender available on these sites. For another, singles are not often open to the idea.

"I think that it's different for everybody," says Tami Starlight, 46, a transgender woman and activist who lives in Vancouver. "I don't think that a person should necessarily have to disclose right away."

Ms. Starlight says some people are afraid of disclosing, or being "out," and also worry about being fetishized.

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"The dynamic is quite complex," Ms. Starlight says. "I don't want people to want to date me …[where] it's just all about sex. … I'd rather have it be way more organic and find a person who is interested in me and the things that I believe in."

For other online daters, personal information of such a calibre can be a lot to process. Rebecca says a million things went through her mind when Alex told her about his previous life. "I was floored," she said. "But all I could think about was how wonderful he was and how much I'd come to like him."

Says Alex, "I remember this amazingly sensitive and kind thing Rebecca said, later in the date. … She said, 'I've been thinking and, had I told you what you just told me, I'd want to hear this: You should know that this does not change how I think of you at all. You're still this amazing guy I'm dating.' "

Rebecca's willingness to get to know Alex better paid off – the couple will be married next summer. There will be obstacles in their path, but they hope to overcome them together.

"He's an amazing human being," says Rebecca. "He's caring. He's hilarious in a dorky, nerdy, really fantastic way. He makes me laugh so hard, I cry. … He's the love of my life. I can't wait to see what the future holds."

Special to The Globe and Mail

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