How can I tell my closest online friend that I'm actually male?

Question

Preface: Some folks will think I'm a terrible person after reading this, and perhaps they're right. In truth, there were several points early-on when I'd thought about breaking things off, but something always drove us together. What I've detailed below is simply the product of wonderful happenstance.

Background

I'm a guy in my early twenties who loves to write, and as it happens, I enjoy pursuing online roleplays with other writers. As it also happens, most of the characters I'm inspired to write happen to be female. In days past, this hadn't presented a problem, right up until I met Jay.

Jay isn't his real name, of course. Like me, he's a writer who's comfortable with depicting both male and female characters. Unlike me however, he had the courage to disclose his identity from the get-go. I myself was skittish, as most of my past partners would've found it rather unsettling for a guy to depict female characters. When the topic came up, I lied and told him I was a girl.

Meanwhile our characters interacted, fell in love, and eventually even proposed to one another. The story's all but fallen by the wayside, but I'm entirely certain our actual friendship was the chief reason it occurred.

On that note, Jay happens to be bi just like me, and even had a husband till he passed away in tragic circumstances. I only mention this as it might make him more accepting of the real me.

The Problem

After a brief lull to finish university, I started talking to Jay again in January of this year. From the start, we'd both known that real life would be a purely platonic affair between us, yet by some turn of luck we've grown incredibly close to one another. I've even told him I love him, albeit explicitly as a friend. He's served as a lodestar in those terrifying weeks after I was diagnosed with chronic pain, and I've helped him through some of the worst days of his own life. In fact, aside from a pseudonym and a fake ethnicity, every aspect of my interaction with him has been completely genuine.

On some level, I'd honestly like to believe he already knows. Our conversations usually segue into economics and military history, two rather uncommon pursuits for the fairer sex. And though neither of us has ever asked for photos, insofar I've drawn the line at interacting with him outside of the IM app we use. He never even knew my (fake) first name till a few months back, and only since I mentioned it offhand.

Why I'm Afraid

Ever since another of my internet-friends confessed to me about wanting to transition, the thought of coming clean has weighed heavily on my mind. When Jay asked me if I could play video games yesterday, I found myself awash with guilt and grief for the better part of ten minutes. I want to tell him - a great part of me needs to - but I'm deathly afraid he'll react poorly. Even if he doesn't immediately distrust me, I fear the magic would be gone. Jay would soon take his leave, and my world would become just the slightest bit colder.

The Question

I've already made it my mind to tell him who I am. The question is, How can I approach letting him know my gender in a way that's more likely to end with us remaining close friends?

Answer 1

When I was younger I was in a similar situation with an online friend. In my case, I'd told them I was far older than I actually was. I still vividly remember how bad I felt every time I continued the lie and the tight feeling in my stomach when I thought about how I'd tell them.

When I finally told them, I focused on these points:

1. Be straightforward and honest

   Don't draw this out. He'll probably be in shock after you tell him. You won't be able to get that much information across since he'll probably immediately start thinking about the entire friendship. As such you need to clearly and concisely get your points across.

2. Make it clear that you still want to be friends

   Since, again, he probably won't have the capacity to take too much of this conversation in the moment, I'd focus on getting this one key point across. Let him know how much you value the friendship and that you're telling him because you want this friendship to last. This is what you want him to focus on when he's thinking about the situation.

3. Give him time to think

   After you tell him, you need to give him space. He's going to have a lot to think about, especially with how long you've been friends. Don't try to ask him how he feels about it. Don't try to reach out to him asking if he still wants to be friends.

   Let him know that you'll give him the time and space to think about things and that you'll be waiting to hear from him if he still wants to be friends.

   He will make his own decisions, and when he does, you'll find out. It will be very very stressful on your part (believe me, I've been there), but remember that you'll only be hurting your chances if you try to rush him.

Ultimately it's Jay's decision whether or not to continue this friendship, and it's a decision he'll be making himself. All you can do is make sure that he understands that you care about him.

For what it's worth from one internet person to another, I think you should be proud of yourself for taking this step. This is not at all easy, but regardless of what happens, you're coming clean and being honest about the situation, which is more than many people have the courage to try. Congratulations on making this decision and best of luck!

Answer 2

Aww this takes me back... It reminds me of getting to know the first non-cisgender person I ever dated. We met on an online dating app. They were honest about their identity. They were agender. I was just too hetero and ignorant to fully understand what that meant. Looking at their profile picture and talking to them I assumed that they were assigned female at birth, and were just androgynous.

We got to know each other chatting online, over the course of a couple months, in a long distance relationship. Then I finally worked up the nerve to ask them out on a proper date. I was excited, we'd been hitting it off online, really getting to know each other, way beyond the typical small talk nonsense. They were brilliant and playful, and I really liked them.

We decided to meet up at a pool hall, I arrived early because I was worried about traffic and wanted a chance to shake the first date jitters before they arrived.

When they showed up I recognized them instantly, they looked just like their profile picture. But then they spoke, and I'm ashamed to admit that I was a little taken aback at first... I realized that my assumption was incorrect. I realized that the person I had been falling for online wasn't who I assumed they were...

I could tell that they were aware of my shock, and felt awful. This wasn't their fault, it was mine. So, I decided to be a decent human about it. If nothing else I could give this person I'd gotten to know online a chance and a nice night out.

That was the first crack in my hetero facade. I wouldn't say I was closeted, I just thought that plumbing mattered, and this was the moment that I realized that for me, it really didn't. I liked them, their quick wit, their playful nature, their heart. They were the person I got to know, they just weren't what I thought they were.

I bring all of this up because it seems like you find yourself in a very vaguely similar situation. Very vaguely similar you really should have been honest. But it sounds like you may have been talking to someone who wouldn't have cared about your gender to begin with. You're both bisexual, so you're a little less likely to run into a wall of homophobia.

The wall you're more likely to hit is that one concerning honesty and trust. Admittedly, that's a pretty important one. I'm not going to beat you up over it, you're already doing that on your own. Live, learn, and don't do that again.

So... What can you do about it, beyond not doing it again?

Well... This is one of those fall on your sword and hope for the best situations. You did the wrong thing, you know you did the wrong thing, all you can do is confess and hope for the best.

Probably better not to try to hide behind caveats and excuses for why you did what you did. Just be honest.

Bringing this answer full circle, you may be pleasantly surprised, if you decide to do the right thing. They may not care as much as you think. I was a "straight dude" and I didn't. They'll probably be a little put off that you weren't honest, but you may luck out and they may forgive you. That's the best you can hope for.

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Also... And I know you didn't ask... But...

This whole collaborative story writing thing sounds like an epic flirtation. If that's the case, you probably ought to be honest about that too, it may pay off ;)

Answer 3

Had a very similar experience even if the reason was different, I faked to be a girl because I thought it was easier to make friends on the chat I used to write in (at some extent it was actually true).

One of my friends was a girl (Jane) of my same nationality and I very liked her. I had to see her date other guys while I was stuck in a golden prison I did built by myself: I was popular in the chat, everybody liked me and I felt so good being appreciated for my personality without the burden of my physical body that never made me feel confident in my social relations.

I was friend with another girl (Alice) that was a good friend of mine and we understood each other.
One day Alice asks me if I'm okay if she turns on the webcam, I agree and a visibility shaken emotionally guy starts to tell me his story and why he faked to be a girl and talked about some problems he was having in real life.

At that point I felt obliged to tell the truth as well and we spent the night talking about our own experiences.

We became good friends and even started to hang out in the real life for some time.

Meanwhile he helped me to tell the truth to my other friends, included Jane.
Some of them were pissed of by the situation while others, included Jane, accepted it and decided to stay friends for the time begin, even thanks to the help of Jane that took my defenses, years are passed and we are still good friends.

Just for completeness, I'm going to marry with Jane in September!

I hope my story helps you to understand what may happen. I don't think there's a magic recipe to maje more likely to stay close friends. Every person will react differently, depending by what you did while you were behind your avatar they will accept the reality more or less easily. But staying in your situation is not going to help you in any way, what you get in the virtual life remains there, you deserve more.

Possible advices based on Alice's and mine experiences:

If you have commom friends in the same online community, try to tell to your closest one the truth, then she/he will be able to help you with Jay reaction like it happened to me maybe.

If you are in very close relation with him (like, sexting or similar) try to reduce or stop it and wait some time before you reveal the truth, it will make less likely to him to react very badly if he feels betrayed by you.

If you want me to articulate better some part of the answer please just leave a comment.