I'm considering coming out, but I'm not sure how I should do this. Is there a method to coming out or am I overthinking this?
There are different methods. In person, over the phone, over skype, on video, hand written letter, typed letter, e-mail, sms, the list goes on. What is your usual/preferred type of communication that you use when you're talking to the person that you're thinking of coming out to? If this isn't what you meant, feel free to clarify.
I'm still in high school, so really I'm trying to find out how I should come out to my best friend. I'm going to come out to him first because my family is more conservative and my friend is more liberal and more likely to accept me.
Do whatever comes naturally. Although face-to-face is more difficult, I feel it's more rewarding in the sense that you get their initial reaction as well as their thought-out response. If that's not something that you're comfortable with, sending an email or a text or even a phone call is a perfectly normal way to come out.
What I need to know is how should I say it, obviously I'm not going to suddenly say I'm trans. But how should lead into it?
That's a difficult question and one that you will probably have to find the answer to by yourself. Nobody can really put into words exactly what's happening in your circumstances. The easiest way to do it is to just be blunt and honest, speak from the heart and it will show. The hardest part, for me, is saying the words out loud and I often find myself stuttering and trailing off halfway through a sentence because it's so nerve-wracking. Be brave x
Maybe then it would be better for you to just send a text message or an email, whatever you main form of contact is other than the telephone.
I think I need to come out face-to-face for self confidence reasons. Because I don't think I would be able to come out to my family( which is going to be very difficult) if I can't come out face-to-face to my best friend.
Do it in person, otherwise you leave yourself open to the "no reply, tormenting" situation. You need to know/see their answer, in person... and answer any questions they might have. Online, they can simply ignore you and drift away, depending on the person they are. It's not personal enough. That being said, just be casual about it. If you make the atmosphere tense, then expect a similar reaction. To one of my friends i was like this... We walked and were talking about girlfriends and shit... me trying to avoid male or female pronouns and when he asked me... can't remember what exactly, i just went - "oh yeah, btw i'm gay" (since, easier to explain than pansexual). And he was quite okay with it, in fact... later that day, got somewhat "mad" that i didn't find him attractive, as compared to a mutual friend we had. As said, be casual, don't make it a big deal, tell them, like you already expect them to be accepting of it. If you show them that you anticipate a rejection... then, yeah, you get the point, i hope.
If you're pretty sure they know what trans is, that makes it a lot easier. I'd keep it pretty casual for a bff situation. Someplace you hang out together regularly, no big surprise outing or they will be suspicious and may make it weird.