I started transitioning last summer (2017) in early July. I had broken the news to my own mother in a somewhat awkward fashion immediately after receiving my first round of prescription hormones. While she was shocked at my revelation, she promised to never stop loving me. My father said the same thing.

Parents (and siblings) are generally the more accepting family members based on my own experience and hearing testimony from my other trans/non-binary friends. However, when it comes to older generations it can be more dicey and rocky. If you are thinking of coming out as trans to older family members and relatives, there is no going back. If you truly value your relationship with them, telling them may feel you're being honest with them and they should appreciate it. But if you feel they won't accept you, ask yourself if having them in your life is worth the pain of them rejecting you. Depending on how religious or conservative they are, that adds into their reaction too- but I feel all family should be given a chance.

My case and point:

I had difficulty coming to terms with my grandfather (my grandparents are divorced, and my grandma was easier to talk to) and his mother in her 90s (my great-grandmother). Both of them are staunch Republicans who voted for Donald Trump in the 2016 elections and still support him as well as using FoxNews as their primary news channel. I'll never forget the day I told him 6 months into my transition. On a visit to his mother's house one weekend, he and I went out for lunch out a local diner. Upon ordering, I broke the news to him. To say he was shocked is an understatement. He didn't reject me or react negatively, but he felt completely blindsided. I love my grandfather dearly and he knows it, but I felt I was lying to him by not telling him and leaving him out of the loop. He appreciated me telling him and promised to never stop loving me. After he assured me of his continued love and support, we both agreed to not tell his mother. At that time, I was pleased not to deal with that reality with her advanced age and conservative views.

The next morning, he told me he had trouble sleeping- waking up five or six times. I felt so bad to make him lose sleep and I apologized for springing this on him. He said I had no need to apologize for something out of my control- he mentioned it because he was going to need time to process and learn more topics about transgender people. I promised to always answer any questions he had as well as being patient and understanding with him. It's been almost a year since I told him. He still slips up now and then with my old name, but he then quickly corrects himself. I've grown comfortable with older generations still referring to me by my previous name- but I also feel I don't need to correct them because they know and accept me. Even if it is a slip of the tongue, everyone regardless of their age, background, religions, views, etc. should, to be a decent human being, respect someone's pronouns and name. Always kindly remind them if they slip up and do not correct themselves- remember to not get too annoyed with them and be patient. We're all learning new things every day and trying to better ourselves.