Everyone in my friendship circle knows but one, help?

[Ollie]

As title states, everyone in my friendship circle knows about my transition except one person.

I don't know if he knows or may have an idea of my transition or not. The reason I haven't told this one person in particular is because he fancied me before my transition. It was never overly full on flirting, but he got the point across that he wanted something more than friendship. Anyway, I didn't lead him on or show any interest and eventually he gave up, but I'm pretty sure he resented me for it for a little while...least, at a party he said I was a dick for some reason (and I see no other reason for him to call me that other than he felt hurt that I rejected him).

We stopped talking for a while but then we ended up moving past all that and became friends when he moved into the house I was sharing with my other friends. By then I had my hair cut short, was on T, wore my binder a lot and was dating a girl, everyone in the house knew I was dating a girl. He pretty much saw me as a lesbian because the T effects hadn't changed anything much yet.

I moved out of the house a few months after because I was moving in with my girlfriend. I'd still like to visit my friends occasionally. Everytime I plan to go visit them I always cancel whenever this one person is attending the same event, because I could never show up and be like "yo...I have facial hair and I sound like a man now" knowing that he used to sort of like me or whatever that was.

I have a friend's leaving party to attend in 3 weeks and I really want to go as it's a huge deal, but I don't know how to go abouts telling this person that...well..I'm a guy now. I'm scared to death, partly because if he did resent me for shutting him down then maybe he could easily turn against me when I tell him. I have no idea what to do, it's hard making friends in a new place and I don't want to lose my current friends. I certainly don't want him seeing me differently cause I thought we got along quite well as buddies after the whole thing.

Any tips on what to say to him or go about it? I have 3 weeks before the event so if I tell him I would like to do it soon to let him digest the info before I have to see him. Gah and I thought I'd never have to come out again >.<

[Jessica Merriman]

If everyone in your circle knows and he is in that as well, he knows.

[wheat thins are delicious]

If everyone in your circle knows and he is in that as well, he knows.

This.  Odds are he knows.  Go to the party, if he mentions it, which he likely won't, deal with it in a short and efficient manner "I'm [name] now, that's all you need to know."

[Kreuzfidel]

I'm with the others.  Unfortunately, if he reacts badly - that's on him, mate. He's ONE person - your other friends clearly accept you for who you really are and still care about you.  If he doesn't, then he's a) not your friend and b) certainly not going to turn anyone else against you.

[Darth_Taco]

If he's mad, it's not gonna be because of lingering feelings or your transition. He knew he had no shot as soon as he saw you dating a woman. What would make him mad or even hurt him is the fact that you've been avoiding him and that you told everyone else you two are friends with except him about the major life change you made. Even worse, you've been avoiding him because you don't trust him enough to tell him about your major life change.

All of us here have been through what you're going through right now, so we know you weren't trying to be a jerk. We know how terrifying it is to have to come out over and over again to all the people in your life pre transition. Your friend might not see it like that though. He might think that you didn't think of him as a good enough friend to tell him yourself. Don't forget that he has probably never had to go through something like this, so he really doesn't have a point of reference as to where you're coming from. He needs you to tell him where you're coming from.

Ok, so here's how you try to work things out. Don't wait until the party to see him again. Call him up and make sure to meet up with him as soon as possible, just the two of you. Don't wait until the meeting to suddenly surprise him with your new found manhood either. Make sure he knows about your transition before and that this meeting is to clear the air. Make sure he has a current picture of you so he knows it's you and not your evil twin brother or something. Tell him how scary this whole process is, how hard it still is to come out over and over again, and how you didn't want to hurt him. I don't know anything about your friend, but considering you two were good enough friends to live together, I'm going to assume he's gonna try his hardest to be cool with your transition and understand why you didn't say anything sooner. Then compare beards.

[Ollie]

Thanks a lot guys, that makes sense, I guess I'm just making the fear worse for myself. I feel more confident telling him now.

[Jessica Merriman]

I guess I'm just making the fear worse for myself.

We all did that at one time or another. The good thing is it is perfectly normal to feel that way.