It being, well, you know.
All this.

(TL;DR as hell in advance)

This guy...he's gotta be the strangest person I've ever been friends with. I swear, me and him could be twins sometimes. We're way too much alike. A few months ago I broke down a bit because my binder wasn't showing up, I was freaking out about coming out, everything was getting to me and I called him to see if I could buy painkillers off him. He more or less told me to shut up and vent, wouldn't leave me alone until I told him why I was crying and calling him at 2 AM. We talked for a while, I vented the whole thing out and he said something along the lines of "So? So you're messed up, we're all messed up, and we're all family". It really, really upped my hope. It made me happy as hell.

A few weeks/months/X amount of time later, he'd call me my legal name just to piss me off. Little bit more backstory here, Frank (my friend) is one of those guys who picks on EVERYONE. That's just how he is, that's his way of saying he loves you. When nothing's going on, he's always light-heartedly ragging on everyone, and we all do it back, and it's all good. He said that name, and I snapped at him. I've got serious anger problems, so I try to suffocate that down as much as humanly possible so when he asks me-sincerely-why it bothers me I just keep telling him "Because." It turned into a bit of an argument, and then he apologized, changed the subject and that was the end of it. He also has a habit of yelling "lesbians" whenever we (my girlfriend and me) see him. Admittedly, when I first met him (and most of my friends) I thought I WAS a lesbian. But I've told him so many times, not only am I barely even attracted to women anymore, I AM NOT A DAMN GIRL.

And so it goes back and forth. I'm horrible with non-violent confrontations so a few weeks ago, when it got to the point where I was flat-out avoiding him, I begged Ben to talk to him for me. Because Ben's both better with people and better with explanations than me, and he did, and it seemed that everything finally registered. Apparently not, because today at Wal-Mart today he more or less outed me.

I can't even remember the context because he made some comment, Ben gave me the "Oh ->-bleeped-<- are you gonna be okay?" look and I started getting light-headed. I started getting panicky as hell and shaking, trying as hard as I could to keep it together. Above everything, I will NOT freak out in public. I'm giving everyone a free show of "Watch the freak have a nervous breakdown". I would've rather went into the bathroom, fainted and broke my neck than to embarrass myself in front of everyone. I wish I could remember what the hell we were talking about... Me and Ben were goofing around, I was humping his leg or something and the clerk was laughing her butt off, we're all joking and ->-bleeped-<- and then Frank says -in response to something else- "Yeah, but he's still a boy".  (Pointing at Ben).  The clerk, amazingly, seemed to either miss it or completely ignore it because when me and Ben paid for our separate stuff, she said (and it sounded completely sincere) "You boys take care".

So I was pissed for quite a while, and then some totally unrelated BS made it worse. As Frank's driving me and Ben home (I've calmed down and was at least able to fake a decent mood by then) we're all talking about random sex-related things, and my transness comes up. Frank asks me, genuinely, if I "go through with it" will Julie still stay with me? I told him that I'm pretty sure, that she's taking it better now, and that I don't care if we're not "dating" as long as we're still as close as we are now. He makes that weird "Interesting, I acknowledge that" face and goes "Well, no diggity. That's great to know, man."

So...WHAT THE HELL.
Frank, for all of his posturing and badassery, is one of the most over-emotional guys I've ever known. He's also one of the sweetest and sincerest, when he's being sincere. He's also confusing the living hell out of me. I talked about it with Ben for about three hours, trying to figure out wtf is going on and wtf to do, and I'm wondering if he just needs to be constantly reminded of it. After I blew up at him, he was great about it. After Ben explained just how badly my legal name hurts, he hasn't said it at ALL since. Maybe he's just...incredibly dense?

I don't know, guys. Sorry for the massively long post, I'm just really stumped on this one. I'm not gonna ditch the guy because all awkward moments and pissing-me-off aside, he's a great friend. When things finally sink in, he's good about it. It's just...getting them to sink.

That's really strange.  I don't know.  this seems like it goes beyond regular friendly teasing, and yet sometimes he's supportive?  Is it possible he's not aware how much it bothers you?

I've been friends with people like that.

Basically, the issue is that some of their social skills are underdeveloped. I don't mean that as an insult, just an observation: people (especially boys) who have trouble reading other people often discover that insult comedy is a fairly easy way to make friends and put people at ease, so they rely on it pretty heavily, especially in group interactions.

The problem comes in because they don't have a strong natural sense of the line between "funny because it hurts" and "not funny because it hurts." And because they often have trouble reading people's nonverbal responses, they often don't know when they've crossed it - some don't even learn it exists until well into adulthood.

The solution is to be extremely direct. When they say something that hurts and isn't funny, get them alone, look them in the eye and tell them very bluntly "Please don't (call me a lesbian/imply that I'm a girl/whatever), it's not funny and it upsets me." If they ask why, stay calm and assume that they're genuinely curious - that they really don't know why this one particular thing is in the "bad" category while other things are in the "OK" category. Assume good faith, and try as best you can to actually answer the question. For instance, explain that you wouldn't have gone to all the trouble of changing your name and coming out to all your friends and risking your relationship if you were OK with being seen as a girl and a lesbian and called by your old name.

I think that kyril has nailed this one (as usual ). I think that males who have been brought up in a male society are far less concerned with emotional understanding than a guy brought up in a female society, where there is an 'expectation' to analyse emotive problems and deal with them.  In male society such things are either dismissed or treated as a joke etc. Guys displaying emotions are thought to be a bit strange, unless it's at a loss of sporting event

I think that females brought up in male society have similar problems of being regarded as non-empathetic with other woman.

You need to tell him the boundaries.

Good Luck

Cindy

Thanks Kyril, I'd say you're definitely right, and I'm realizing that's really my only problem with this guy. He's so smart, she's got infinite potential to be an amazing person but it's like he's spent so much time downgrading himself he lost himself somewhere along the way (I'm sure the 15 years in and out of jail didn't help).

I'll absolutely try this, when it's NOT directly relevant. One of these days I'll text him (as much as I hate texting, he never answers his phone) and explain it all our.
I love you guise (and gals), I'd lose my mind without all the advice.