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My Boyfriend Discovered I’m Trans, And Now He’s Not My Boyfriend

Tonight I wiped away tears, waiting for a phone call I knew would never come. Phil, a handsome man in his early 50s with salt and pepper hair and dazzling, deep blue eyes, had promised to call me, to talk about what he had discovered about me online.

Phil learned the truth that I had hidden from him: I am a transgender woman.

And so today, on the cusp of a romantic weekend we planned to spend together, he dumped me in a text message.

“I can see us as friends in the future, but not intimate.”

He made two main points, and said he’d give me a chance to respond when he called me tonight. The first was his chagrin that I had kept him in the dark.

“I am not angry or upset, just disappointed you elected to not be open and honest from the start,” Phil texted, and my heart sank. “I had a gut feeling you were holding something back, and now it makes total sense to me. Intimacy for me requires trust and honesty above anything.”

I can’t deny it; he’s right. I did keep this from him. But the reasons didn’t seem to matter.

As for the second part: by not disclosing my “transition from a man to a woman,” as he called it, I had wasted his time. Wasted those kisses. Holding hands. Calls and texts and plans and dreams. We had hit it off so well right from the get-go, we dubbed the Connecticut taco joint where we had our first date “our place.”

Coming into this as a widow meeting a divorcee, each of us having married our college sweethearts, each of us with three childrentwo boys and a girlwe shared sorrows and joys, stories and secrets just not that big one.

“Realizing what I know now,” he said about my past, Phil declared he actually wasn’t attracted to me after all! Um WTF?

“I think you are an interesting person with an engaging personality,” he texted, “but honestly I have not caught those kinds of feelings I get when I meet someone I find attractive physically and emotionally.”

Oh, okay; he now says he didn’t find me attractive. Then I guess scenes like this were just accidental lip-lock. Riiiight.

Of course I knew that by keeping my gender identity a secret that this might happen. I was ready to tell him I was trans at several points during the 20 days, two dates and 120 texts since Phil connected with me on a dating app. But each time, I hesitated.

Why is complicated.

Maybe He Already Knows?

“My hometown is very LGBT-friendly,” he told me out of the blue on that first date. “And I myself am very progressive.”

Oh? “Who says that on a first date?” I thought. The most likely answer, I figured, was that perhaps he had “clocked” me as trans and that it didn’t matter to him. If I knew this to be true, I would have told him right then and there: “Really? That’s great, since I’m transgender!”

But I didn’t. Instead, we split the tab, braved the crowds at Hartford’s St. Patrick’s Day parade, and held hands as we walked and talked, before sharing a first kiss as we said goodbye. We agreed to a second date right on the spot.

Date two was this past Sunday in his Massachusetts hometown, his treat. Phil got tickets to the wonderfully romantic Irish play, Outside Mullingar by John Patrick Shanley. We laughed, I cried. We enjoyed wine before the show and split a carrot cake at intermission, then dined on calamari and fancy schmancy pizza and much more wine. I felt a buzz, and it wasn’t just the alcohol. We confided in one another that we were not interested in seeing anyone else.

But I still didn’t tell him about my past. Other secrets I kept to myself that night: I hadn’t had a second date with any man, ever, and I knew I was falling for Phil.

Staring into those deep pools of azure blue that were his eyes, I realized that for the first time in my life, I had a boyfriend. He was mine. And I wanted him to fuck me.

For weeks I had been consulting my girlfriendsa circle of eight other widows, all of them cisgender and straightwho agonized with me as I tried to make sense of my decision to hold off telling him I’m trans.

“I think you are putting too much pressure on yourself not telling,” said Donna. “I’m just curious why aren’t you saying in your profile or the minute you meet? I want to understand your thoughts and feelings in this.”

This issue of disclosure is controversial both inside and outside the transgender community. And as I explained this to my widow sisters, I knew that to someone who never questioned their gender, even these most sympathetic friends, it seems nonsensical to conceal the facts about my past.

Not Your Typical Trans Woman

In a nutshell, I was assigned male at birth but I knew by the age of five I was a girl, and at the age of 12 my mom helped me start living part-time as a girl. For all of my childhood, I was an actor and fashion model, and eventually modeled as a girl, too. I developed breasts, due in part to a hormonal imbalance and five years taking 1970’s-strength birth control pills.

But by my teens, my father tired of mocking my femininityhe’d call me “Mary” and direct me to “cut those nails, or paint ‘em!” and to stop fussing with my long hair. He told me to ignore taunts from other boys who also called me names, including “Tits.” He sent me to an all-boys high school and tutored me on how to date girls (or try to).

Girls invariably told me, “I don’t know what it is, but I feel closer to you as a friend, than as a boyfriend.” One even said, “It’s like we’re sisters!” But I kept following the script my dad had written, and managed to put aside my feelings. A former girlfriend who is now one of my closest friends reminded me I was a raging homophobe, most likely the byproduct of denying who I really was. I married the first woman I had sex with, and we started a family. She said she liked that I was a “sensitive man,” unlike any other guy she’d known.

I even grew a denial beard in my pretense of being a man.

It was not until a decade later, following my father’s death and the birth of my youngest child that I finally considered that I did not have to keep pretending to be someone I wasn’t.

In fact, I breastfed our son. But that’s a story for another time.

Fast-forward a dozen years and here I am, having more success in attracting men than I ever did any woman the last time I dated back in 1994, when we placed ads in a newspaper with a code and a phone number. To meet your prospective date, you’d first listen to them describe themselves, then leave them a voicemail.


Full Disclosure Can Be Dangerous

The more bold friends of mine who are also trans and looking to find a male partner have taken a different approach to online dating. They disclose right up front that they are trans women. And the result is an onslaught of hate from mean-spirited lonely men who punch down with hurtful messages, disgusting insults and anti-transgender bigotry. “Chicks with dicks,” “man in a dress,” and worse. My friends also must deal with “chasers:” those men who get their thrills dating and having sex with pre-op trans women. No thank you to both.

If Phil had played his cards right, we’d be having sex this weekend, but not until I told him the truth. If I didn’t, he’d never guess just looking at my body, but I couldn’t be that intimate without sharing my secret. And he might complain that I was too tight and lacked proper depth, problems I’m having addressed in major surgery soon. Funnily enough, that’s one thing I did tell him on our last date.

So why not disclose that I’m trans, too, as Donna suggested? First because it’s my personal, intimate business, not his. Would it be fair to ask him about his most recent prostate exam? That level of intimacy, to my mind, takes awhile. Same goes for my gender identity. I’m a woman, and being trans is perhaps the 6th most interesting thing about me after mom, widow, Irish, journalist, and terrible driver.

Another big reason to delay disclosure: Out of fear for my life.

In 2017, 28 trans people were murdered because of who they were. In the majority of cases, the men who killed them claimed they felt deceived by their victims. It’s been dubbed the “trans panic defense,” and in some places it’s outlawed as a legal defense. At least six more trans people have been killed as of March 2018, and as is true every year, most were trans women of color.

While I’m not a POC and didn’t think Phil capable of such a horrendous crime, I don’t know him well enough to totally rule out what any man might do if enraged.

In August 2017, the nationally syndicated radio team called the Breakfast Club made headlines when guest rapper Lil Duval suggested trans women are trying to “trap” straight men and trick them into gay sex. What was worse was what he said he’d do if that happened to him. “This might sound messed up and I don’t care,” he said on the show, “but, she dying,”

So it’s not uncommon for men to think that if they have an intimate relationship with a trans woman, it means they’re gay. “You manipulated me to believe this thing,” Lil Duval said. “My mind, I’m gay now.”

Because they cannot see trans women as women. We’re just men who look like women. They don’t understand gender is what’s between our ears, not what’s between our legs. And here’s a newsflash: Not all trans women have penises.

Waiting For The Right Moment

Phil never considered my side in all this. Then again, he is a man.

“If you are out professionally and with your friends,” he texted, “why not with me?”

Well, after two fabulous dates, I was indeed ready. Had I not been enjoying myself so much, I can see now that it might have been easier for me to tell him at the end of the second date, or over the phone or via text following that wonderful afternoon and evening.

Instead, I planned to tell him about my past in person, on our third date this Sunday, which also happens to be my birthday.

“Do you think anything would have changed if you told him earlier?” asked my widow friend Sally. “And does that change your desire to wait? I feel men in particular are not as open to this.”

I agree, I told her, but had I told Phil earlier, I have no doubt we would not have enjoyed these three weeks of romance.

The Numbers Don’t Lie

Based on recent polling, the prospects for me having another relationship as a transgender woman are getting slimmer.

The May 2017 survey by YouGov found 27% of respondents would not even want to be friends with anyone who identifies as trans. That’s more than 1 out of 4 people who would turn their back, rather than be my friend.

Even fewer people, just 17%, said they would consider dating a trans man, trans woman or non-binary individual. Only 18% say they would consider a “serious” relationship with a trans person. Those willing to have sex with a trans man or non-binary person amounted to just 15%, and only 13% said they’d get intimate with a trans woman like me. Trans lesbians like my friend and YouTube personality Maia Monet face even stiffer odds, a smaller dating pool and the same transphobic misconceptions from their potential same-sex partners. It’s not just straight men who see us as fake.

Adding insult to injury, pollsters reported only 4% of Americans surveyed admitted to having gone on a date with someone trans. Even that dismal number seems generous, given my personal experience.

When I set the filter on my dating app to screen for men who answered the question, “Would you date a transgender person?” I have to zoom out the search to 200 miles from my hometown to find anyone. Right now there are only two guys who said yes; one of whom is himself trans, and the other is looking for a polyamorous partner. Yeah, no.

My Own Bias

Is that unfair of me? Am I not as bad as Phil if I won’t date a trans man? Well, my very clear preference is to date straight cis men, so I’m not looking to meet a trans man. But trans men are men. So, if I were to date a guy and develop feelings for them, then learn they were trans, I would not automatically dump them. Same goes for a bisexual man, because I know plenty who form happy monogamous relationships. I’d give either man a chance. Having already fallen for the person, I wouldn’t focus on the label or their past.

But that’s me. That is clearly not how Phil thinks, and I have to respect that at least he didn’t just ghost on me, and that he let me know what he was feeling. Even if he did it via text. Even though he never did call.

I’m done crying over him. I’m not interested in being friends with someone who doesn’t tell the truth about their feelings or changes them upon learning something that makes me different from all the other women he’s dated. The life I led before I came out makes me a stronger woman today.

Google Is My Enemy

Searching for “Dawn Ennis” on the internet yields dozens of stories about my coming out as the first trans journalist in network TV news, about my mental health crisis and frightening delusion and detransition, then getting fired by ABC. Prospective dates can watch my talk show on YouTube and read my blog and the hundreds of articles I’ve written about LGBTQ rights. They will see photos, many of them of me before and after, or with my late wife. Our nightmare of finding reporters hiding in our bushes, ambushing our children and harassing our neighbors about “the tranny next door” endures forever on the tabloid sites that turned me into a laughingstock, and cost me my award-winning, 30-year career in television news.

Transitioning, I tell those who have invited me to speak at conferences and on panels, is hard enough; to do it without screwing up while under the bright spotlight of the media is next to impossible. I wasn’t a celebrity but I was robbed of my privacy just the same. And because nothing goes away on the internet, anyone who even considers dating me has all this dirt at their fingertips.

I was foolish to think Phil wouldn’t find it eventually.

What I had hoped is that he was someone who didn’t care about all that. I hadn’t told him my last name. I didn’t invite him to be my Facebook friend. But found me he did. Game over, man (in a dress).

Since he didn’t call, I wrote Phil one last text tonight, and hit SEND.

“If my past is enough to rule out your potential future with me, fine, keep your distance, and frankly I feel that’s your loss.

And even though part of me felt sure you must have known I was trans and weren’t letting on, I’m convinced if I had told you up front, you’ve made it pretty clear you would never have given me a chance.

That was all I had hoped for. Not to deceive you or play a trick: to have you see me for who I am first, rather than a label. I leave you with this thought: ‘a difference that makes no difference is no difference.’”


Dawn Ennis

Dawn Ennis is the host of 'RiseUP With Dawn Ennis,' as well as a writer, editor, producer, and blogger.

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