Jerry is pretty much how I know coming out to my mom, eventually, is not going to be easy. Of everyone in my family, she'd be the most tolerant to it, and... it's not going to be an easy go. If I were simply gay, she'd be fine with it. But transgender and gay? She'll end up asking me "why not just stay male?" Just because it might be easier doesn't mean it feels right, you know?
The good news, I guess, is that at least it's not going to be a question of how she'll react.