Coming out to a best friend

[Camfer]

I think your idea will surely work, but why wait? You could use your draft letter as notes for your talking points and just call him up tomorrow and tell him. That way, by the time you take that trip next month it's all been processed and you can just enjoy your time together. You don't have to be good at talking about this, just say what you need to say as awkward as it may come out. You don't get points for eloquence as there are no judges listening in on the conversation.

From the contents of your letter it seems like there is some chance of rejection, perhaps just all made up in your mind, or perhaps real. Coming out during a two hour journey and getting rejected would make for a long, strange journey.

You should certainly drop the stuff about not holding his potential rejection against him. Why say that? If I lost a friend because I was other than straight, hell yes I'd hold it against him. It sounds like you still have a lot of internal shame, that it would be just perfectly understandable for people to reject you because you are gay. That is something worth overcoming. If someone rejects you because you're gay, that person is the one with the problem, not you!

Now, why can't Eileen know too? You are trying to pull other people into your closet with what you think is some big secret. Tell them both. Not sure what the big deal is. You already know that they know, so just go ahead and talk about the elephant in the room. They may be relieved to hear you finally say it.