I've been out to everyone close to me with exception of my father for about 9 months now.  My explanation to him for why I was coming home from the Navy was a depression diagnosis instead of saying the truth that it was gender identity disorder that disqualified me.  When I told him it lead to a bonding moment as he opened up about his own bouts of depression and therapy that I had never known about until then.  He told me he was still proud of me and there was no shame in having to deal with depression.  Despite that bonding moment, I still couldn't open up to him.

I moved back to my hometown in mid-December, and since then I have only seen him in person three times.  Every time we're together I feel awkward now.  I've hidden it from him my entire life, but no that I am out to everyone else I feel like I can't talk to him.  On top of that, the VA is ready to start me on hormones, but I've said I feel like I need to tell my Dad before I start.  It's not like he can change my mind, but I feel like he is owed a discussion before I start, and not telling him about something so important isn't fair to him.

Because I am distancing myself from him because of not telling him and it is my only barrier to starting HRT, I need to tell him now, but that terrifies me.  I'm not so much worried about him rejecting me, but it destroying our relationship.  I am his only son and named after him.  We've always had sort of a stereotypical father-son relationship.  And while I know transitioning won't change who I am at my core and I can continue to bond with him over the same things, I don't think he will see it that way on his end. I just don't know if I can take seeing his reaction, and I know the best way to convince him that everything will be fine is to tell him with confidence, but 'm so scared I know I won't be able to. 

Would it be lame if I told him through email? Would getting sloppy drunk and then calling him to tell him via liquid courage be a bad idea? Anyone in a similar situation have advice?

I think that "packaging" is important. Can you let him know that the depression is linked to trans stuff instead of saying that it wasn't depression? Or were you going to do that anyway? I just think that you ought to try to maintain that depression connection because of his struggles with a mood disorder.

I would not advise you to come out while drunk. That can go very badly.

Start writing a coming out letter to him. Later, you can decide how to use it. You can mail it, e-mail it, read it in his presence, let him read it in front of you, or use it as a way to get ready to come out verbally. I'm sure there are other options as well. But you can't go wrong if you start writing now.

Do you have plans to maintain that name link? You can take a female version of the name or maybe even leave it as is and use it as a middle name. Depends on the name.

FWIW, I envy you in a way. I cut myself off from my parents and am only now reestablishing contact after nearly three decades of estrangement. You already have a relationship. So I have little to lose, but I don't know how to proceed. No idea. You, on the other hand, have something to lose, but you have the possible advantage of the preexisting relationship. I think that if you look at this as an advantageous situation--something to build on--instead of as something to lose, you might be able to find the courage to see it through.

Coming out to my dad was probably the hardest talks I ever had with him. Guess I was afraid of disappointing him and being disowned. You never really know how they will react. Mine told me he would always be my dad and love me, that would never change, but he really didn't understand all of it. That's been nearly 6 month ago and neither one of us have mentioned since until two days ago I had gone to his house to have breakfast with him and my step mom. As I was leaving he made the comment about how much happier I have become and then he said I was looking a lot like my mother and my sister. If you have a good relationship with your father I would say face to face is best. And absolutely DO NOT do it while drinking that almost always turns out bad. I tried this one with my adult son and it turned into a huge fight. We're still patching things up from this. Can't help but think things might have been better if we had been sober and doing stuff we had always enjoyed doing together. 

I appreciate the advice, but I just drunkenly sent him an email.  Oopsies