This person told my wife years ago, but kept it hidden from me because they were worried about how I'd feel towards them if I knew. In their mind I was this macho type dude who might think less of them. When I found out they were dressing as a woman often it didn't phase me one bit, same person I've always known.

I'll be honest. It's harder to transition later in life because hormones effect people differently. So just be as supportive as possible for her. I'm currently going through the same process at age 30. The emotional toll will occur because it's like going through a second puberty.

..as this is a journey for you as well

Since you’re so close, you may feel comfortable telling them that you fully support her decision and want to support her in ways that work for her. It may just be hanging around with her and being there for her in a variety of situations.

We have a friend who transitioned a little over a year ago. Her biggest challenge was transitioning in the work place where she had worked for years. She said it would have been easier changing jobs, but her entire career/seniority could be jeopardized.

Just be a good friend.

We go on outings together, do church stuff together, we help her with her transgender outreach initiatives that she has been working on, etc.

Good for you for asking, but it sounds like you have a pretty good handle on it.

My youngest child announced they were non-binary a few years ago, shortly after puberty. The hardest part for me, honestly, is the singular "they/them" (I'm a grammar nazi of the highest order). But I make it work because I love them and want them to be happy.

Pronouns aren't the most important thing, but they are important, so make sure which ones your friends prefers (and it's okay to ask), and then use them.

Cute story: When I was talking with my NB child once about the difficulty transitioning, they said, kind of tongue in cheek, "For me, it's all about boobs and pronouns."

it took a little getting used to, but if anyone i know is a true fae, it is faer,

you watch a trans person transition, you often get to see them "blossom". My child was always precocious and smart, but once they came out, they took on this new confidence and awareness.

I couldn't be more proud of them.

(Better yet, ask what he pronouns are, and then use them). I noticed you used they/them and male. Most trans feminine friends of mine use she/her. Try to use her new name (using her dead name is even rude than mis-gendering her). One trans friend of mine said they tolerate clearly accidental use of the wrong name/gender for the period of time you knew her under a different name/gender.

Don't assume there will be any surgery. It's expensive, and generally not covered by insurance. Not all trans individuals want to have surgery. If there is surgery, don't assume how extensive it will be. And unless you are in the habit of discussing anatomy with your female friends, don't go there unless invited.

You've actually known her as a woman for three years. You were just mistaken as to her gender. Especially older trans woman have usually known most of their lives, but never felt free to be something other than how the world perceived them. My high school sweetheart transitioned at roughly that age - and had known since she was 5-7, and had largely given up on being able to live as herself. It is somewhat akin to learning that the light-skinned friend you assumed was white is actually black. That friend is exactly who she was before she revealed her true gender to you.

And on that note, you may well have said things in the past that you would have chosen not to say in the presence of someone you knew was trans. I believe I remember sparring with you about trans women in sports, for example. (I am pretty sure we've sparred recently - and I noticed a strong overlap between the groups i was sparring with over both trans women in sports/puberty blockers and mask wearing. My search only times out this morning, so apologies if you weren't among the former group). Anything you said is mostly water under the bridge, but there may be a measure of things said that can't be unsaid, that may come out when things get tense if she gets comfortable enough around you to let down her hair.

Try not to be defensive. Listen. Listen at least twice as much as you speak.

Offer your support, and continue to see her in the same ways you always have. She may be sensitive to changes - including those based simply on assumptions that her tastes changed with gender disclosure, because LGBTQI individuals can never assume our friends will remain friends once we reveal ourselves.

Educate yourself, rather than expecting her to educate you. Asking here is a good first step. I'll send you a link to my high school sweetheart's mid-50's transition blogs by DU mail, once I get back to my computer. (She is relatively well known in some circles, and would easily lead back to me in a way I'm not comfortable with in an open forum.)

And I most certainly would have come down on the side of let them play. The Republicans are creating laws for a problem that simply doesn't exist.

Must have been the mask threads. They were going on at the same time - and I know there was some overlap (but I'm generally pretty bad at remembering names).

chances are you will make some small slip. just dont be defensive.
your heart is clearly in the right place.

maybe send some flowers if it's that kind of friendship.
you'll be fine.

It leaves me with a funny feeling. I believe this is honestly where some people are in their feelings about it. While I am completely accepting of my friend, and so is my wife, I also know that I will be uncomfortable explaining to my family or other friends what is going on with my friend who is transitioning. It's not a comfortable thing to imagine if my elderly dad asks me what the heck is going on with my buddy? It's not a comfortable thing to imagine questions from co-workers. But when I think of this, I think of how little courage it actually takes from me to tell someone it's really none of their business, or to tell them that's who that person is now and leave it at that compared to what my friend is struggling with and has been struggling with. But yeah, that's not something I look forward to, but it's what's right. I'd prefer not to have to explain anything to anyone, that'd be easiest for me, that's my honest answer, but that also would not be fair to everyone.

That's not something I should be struggling with, but it is none the less. I know what's right. But there are still very conservative sentiments about gender identity built into the world all around me. I'm not resentful , because this is an opportunity to grow and help others grow, but I am apprehensive about how to go about things. I get it, this is not about me, stop making it about me, but I did mention that this is very public, everyone knows how close we are to this person, they've spent Christmas with our families. This person will very likely be on local TV this Fall as a woman talking about their transition, that's already in the works. So this isn't something I can ignore. I'm not going to pretend it's no big deal, I'm going to be an advocate, because that's who I am as a friend. Just not sure what works best.

Transition leaves every transwoman a mess of one sort or another, for the first five years or so.

It’s probably Among the most difficult things to undertake in life, even if you don’t have a family or other commitments.

Your friend will struggle w things that you can’t fix, or might even think are impossible for her to fix, and ultimately what will help most is reliably being her friend and keeping your boundaries intact.

I'd add a few items.
1. Realize that this person has most likely been dealing with this their entire life, frequently starting in puberty if not earlier. It's not just obstacles likely to be faced, but it's obstacles faced.
2. Use your friends preferred name and pronouns.
3. Don't assume anything about her plans regarding transition. Medications and surgery are very personal and frankly it's not necessary to talk about unless it's brought up by her.
4. Please watch your terminology. "Tranny" is offensive. "Transgender Woman" is acceptable, but I prefer "transgender".
5. Remember we all make mistakes in life. Relax a little and don't stress about assumed things.

It would make me feel better about becoming feminine and be out.
She is lucky to have you as a friend!
I have transitioned a little and love the way I feel but besides wearing jeans and tops and growing my hair I've made liittle progress in years.