My emotional dumping this morning (thanks to everyone who answered and shared advice! 
) has really solidified my belief that not being fully out is the source of a major chunk of my distress at this time.
It's going to take a little while to properly set up this conversation with my family, but I feel like I need to prove to myself that I'm not just going to delay these difficult conversations anymore.
It's time to tell my closest comedy friends. The ones I'm afraid to lose.
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@aprilkirby
If coming out trans is anything like coming out gay, you may lose people, and it may hurt a bit. Until you realize the people you "lost", you never really had in the first place, and the peace and strength you get from being honest and open is worth the pain.
@ScottSoCal @aprilkirby I agree, if they walk away from you for revealing your true self then they are demonstrating that they were never really friends