"How was it coming out to your family?"
If there's such a thing as a Universal LGBT Experience (and I'm not at all sure there is), then the phenomenon of "coming out" - disclosing one's sexual and/or gender identity - would be a central pillar of that supposedly archetypal Experience. After I came out as gay, in mid '90s Scotland, I was frequently asked by other gay people how it had gone. Were my parents accepting? Had I encountered any flak?
Everyone had their story to tell, and some were comical. My first partner described how his father had reacted with bemusement. "But you can't be," he insisted, "you've got a beard." Dad, bless him, had been under the impression that gay men lacked sufficient testosterone to grow facial hair.
Of course, this took place in those mistily-remembered pre-Internet Days of Yore but, social media notwithstanding, many of the anxieties around coming out are as pertinent now as they were then, particular for trans and non-binary people. As increasing visibility of LGB people in the mainstream gave a frame of reference for straight people, so the current Trans Moment (and I use that phrase with at least half a tongue in half a cheek) provides a starting point, at least, for disclosing gender identity to cis family. If they've seen Riley Carter Millington, as Kyle in EastEnders, coming out to his screen half-sister Stacey, there'll be inklings of how this might unfold.
I'm sometimes asked for advice on coming out and, truth to tell, it's hard to give a definitive answer. Every family is different (some would say "differently dysfunctional"), every dynamic unique. Also, I'm ever-wary of edging into patronising psychspeak or, worse, cissplaining. I do think it's possible, however, to attempt some broad generalisations:
There is no Perfect Time. This means that those with a tendency to procrastinate (and, as a supreme procrastinator myself, I can understand this) can find reasons to put it off indefinitely. If you're repeatedly telling yourself the time isn't right, a little self-examination may be in order. Are there reasons concealed behind reasons? A degree of ambivalence?
Telling them face-to-face? Myself, I think this is overrated but, if you're going to do it in person, pick a quiet time, when there isn't too much else going on. Allow them time to ask questions and try to be tolerant of some of those questions being naïve, stupid or intrusive. You've had years to make sense of your gender identity; they may be dealing with it for the very first time.
All at once or piecemeal? It can be useful to have an ally in place (siblings are good for this) but, on the other hand, beware of what I've come to recognise as a somewhat invidious dynamic whereby you tell one family member, who responds that they love you just the same, and that they simply want you to be happy... BUT.
After the BUT comes an attempt at controlling the flow of information in regard to your coming out. The whole situation can probably be represented in quasi-equation form:
I'm fine with it but don't tell (X) because ---> (Bad Thing)
If (X) = an older generation, then (Bad Thing) tends to = "they won't be able to handle it", "their generation don't understand" or "they'll have a heart attack".
If (X) = a younger generation, then (Bad Thing) commonly = "they'll be confused", or there's the vague but alarming intimation of some kind of harm.
Sometimes, this is a conscious attempt to suppress disclosure of your identity for selfish or frankly transphobic reasons. More commonly, it's borne out of genuine, if misguided, concern for you.
Family members are, however, terrible at predicting how other family members will react to a disclosure of trans or non-binary identity. When you do eventually get round to telling (X), nine times out of ten, (Bad Thing) fails to materialise. However ignorant or even outright transphobic a family member might appear when sounding off about Caitlin Jenner or Kellie Maloney, they're more likely to consider and moderate their views when it's their own flesh and blood. With kids, the younger they are, the more readily they tend to adapt to what is, after all, just another fact of the Universe, no more or less exciting than what's for tea tonight.
One of the most lazily damaging lies about transition is the assumption, propagated by certain social workers who ought to know better, that a parent undergoing transition is automatically a matter of concern in terms of child welfare. There is absolutely no evidence for this. In his 1998 paper, Transsexuals' Children, Professor Richard Green interviewed children of transitioners and concluded that
All live with or have regular contact with their transsexual parent. No child has gender identity disorder. No child has had extensive conflict with the peer group. All continue positive relationships with their transsexual parent.
In other words, no harm done. Take any "you mustn't tell (X)" insistence with a pinch - nay, a pillar - of salt. It usually reveals more about the person doing the insisting than anything else.
It needn't necessarily be face-to-face. Personally, I think there's something to be said for the written word in the coming out situation: letter, email, even text. While some might consider it impersonal, telling family in writing gives them space to reflect before getting back to you. They're less likely to say something knee-jerk that they might later regret.
If doing it in writing, do follow up later, in person. Family have an amazing ability to avoid seeing what they don't want to see, and it may well be necessary to ask, "Did you understand what I was saying there?" Depending how you've worded it, they may think you're simply telling them you want to change your name, or to wear different clothing.
Spell it out. If you want them to address you by different pronouns, tell them. They may or may not go with it but, if they don't know it's important to you, they won't know to try. Typically, parents struggle with new pronouns because they've known you longer than anyone on the planet, and therefore have more to "unlearn". Visible and audible physical change, possibly with hormones, can help them make that cognitive shift.
Reassure them that a) you're happy, b) they're not "to blame", and c) you're not becoming a different person, you're still yourself but more so.
Most of all, think of your own safety and comfort. Prepare a bolt-hole to which you can retreat if necessary; if you're unlucky, things turn out badly and the reaction isn't positive. First and foremost, look after yourself.
Tl;dr version: do it on Facebook.