Sometimes I wish my best friend would be my boyfriend.

[Tamika Olivia]

This might be kinda rambly, but if I can't ramble on a forum called ARGHHH! Then where?

I've known my best friend for nearly 12 years, and I've been in love with him for at least half that time. Not continuously, it comes and goes, but sum total. He is smart, funny, kind, hard working to a fault, and we are almost always on the same wavelength. He is the first person I ever told I was trans, he held me as I wept last November, he takes care of me when I'm sick or sad. I can think of no one I would rather do literally anything with, and everything I do is better when I do it with him.

The problem is that I've known him for 12 years, and for at least 9 of those years, he only knew me as a person he thought was a guy. I'm worried that on some level he will always think of me as a guy, and that will bar him from ever wanting to be in a relationship with me. I think that if I met him in another life, as a cis girl, we'd be in a relationship. I think maybe, if I'd met him post transition, we could have an easier time getting past any barriers that exist. But as things stand now, I don't know if it can ever happen. And I'm afraid to bring it up, because I don't want to risk what we do have.

I'm also not sure it's a good idea, even if he did want me. He wants kids, which I don't want and cannot give him. He wants to live abroad, I'm a homebody. There are long stretches of my life where I firmly believe that I don't want a relationship with anybody, and where I'm fine with my future being eternally single. Other times I want to be with another woman, which he probably isn't.

So here I sit, right now in love with a man who may not even see me as a woman. I feel stupid and angry and sad and damn cliché, living the stereotype of a queer woman attracted to her best friend. And I don't know if I want to bottle it up until it fades again, or let it out and see what comes. I don't know if I need advice, though if you have some, toss it out there. I think I just wanted to see the big, dumb, stupid mess written out in plain English. Or plain ramblish.

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[Kylo]

Not much advice to give, even though I had two relationships with my "best [male] friends".

You can never control how someone else sees you. After 10 years and another 6 on top of that with someone else, I still have no clue how these guys truly see me. Or how anyone truly sees me to be honest. And they probably can't fathom how I see them. Maybe it's not that important anyway, provided two people give each other the kind of support that makes a relationship worth the work.

Even with best friends who enter relationships... it definitely becomes more work than just being friends. There are heightened expectations... the stakes can feel incredibly high the closer the bond is. Not trying to discourage you, but sometimes some people can be too close, they can not be escaped from, in a sense. So I'd be sure it's what you really want. I thought the same sort of thing in the past, all I wanted was someone to care about and share things with, but there does have to be that romantic attraction as well and if kids are important, I don't know what to suggest there. I suppose there are ways.... I just don't know how easy they would be to make happen.

I know that I wouldn't be in either of those relationships if I hadn't been seen as a cis female beforehand, but given that I was "already involved" it got complicated. You just never know with some people, how attached they really are. But I guess striking up a conversation on the subject casually might tell you what you need to know about the possibilities.

I suppose all I can really say is that friend relationships are great for when you just need someone to have your back, but you have to be prepared for the depths these kind of relationships can go to. If they're working out it's great, but when there's trouble, man, I have never felt the kind of despair I felt when a person I invested that much into and gave that much to decides to shut me out. It can be the pinnacle of loneliness in the presence of the closest other. Everything has to be paid for, I guess.

As someone who tends to jump into things and used to believe that love can bridge any gap - it doesn't always, and sometimes people are just better as good friends. Even if they seem perfect friends, they can be very difficult lovers.   

[natalie.ashlyne]

I am not good for relationship advice I once said no to a girl that asked me to marry her because I knew she deserved  better than me and we both resent that I said no at the time she is starting to understand it but is still hurt by it. So I would say take a chance talk and explain it may work out. If you don't take a chance you may regret it listen to your heart. That is my opinion

[Lady Sarah]

Sometimes, having an intimate relationship with a best friend that knew you as male can be a bad thing. I did that, and it almost cost me my life, as he became more and more abusive to the point where he stuck a gun to my face in order to teach me how I need to be. He had never acted that way until we started being intimate.

Fortunately, I escaped with my life, and disappeared from the face of the earth for all he knows. Even better, I found someone whom treats me right.

Perhaps it is time for some serious evaluations to figure out what is right for you, versus what you believe you want.

[Sarah_P]

I know how you feel, since deciding to transition, I realized I have feelings for a guy that's been an incredibly good friend for 18 years. He's cute, smart, friendly, and always gets things done. As incredibly supportive as he's been to my transition, I don't know if he'd ever really see me as a woman (I suspected he may be bi, but I'm starting to doubt it). Or is it lack of confidence on my part? Right now we live 80 miles apart, but I'm hoping to be moving to the same area he's in soon (I'm really not moving just to be closer!), so maybe we can hang out more often, and see if anything happens.

Sorry I really don't have any advice for you, but It's good to know I'm not alone in this situation.

[amrisa loftus]

Hey Tamika Olivia.

I was in the same boat as you for the longest time during my transition. I have a best and close male friend I grew up with. He would do all of the things you described. He is very caring and always saying, I'll be here if you ever need me. He has been and will always super supportive of me. He is very straight BTW. 

About 8 years into my transition and 5 years of HRT, I told him I've fallen in love with him. He rejected the idea at first but about a year later, we started to date. Now a year and a half later, we are living together and enjoying being around each other everyday.

I was so worried about losing him as friend that struggled to tell him how I've felt. You can see the post here. https://www.susans.org/forums/index.php/topic,179135.msg1581810.html#msg1581810

My advice, is to find a good quiet place to where it can be just the two of you and tell him. If he is a decent enough of a guy like how mine is, the worse that could happen is he says no. I chickened out and emailed him. The email I sent him is in the topic I linked you.