Apologies for the long post!
The short version is: in April I'm planning on coming out to my best friends, and I'm wondering how this went for other people.
A bit of background - we all turn 50 in the next year or so, we've all known each other since junior/comprehensive school (that's UK, think this'd be from middle school if you're in the US).
We're the kind of friends that can go a long time without seeing each other but then pick things right back up when we do as if there'd been no gap. And during the late 00's and 2010's that was prety much the case, families and careers meant we rarely met up, life just got in the way. One good thing that came of the pandemic was that we started to have regular Zoom calls, catching up and doing things like group movie viewings together. Once covid died-down we agreed we should have a regular meet up of just the guys at least once a year.
There's six of us, but one moved to a different country so regular meetups are tricky (we went to his surprise 50th birthday party last year) and one has slowly distanced himself from the group over recent years (I think his wife doesn't approve of us for some reason).
That leaves the four of us. We've booked rooms at a country hotel in a nice scenic part of England at the end of April - a two night stay from lunchtime Friday til Sunday afternoon with the plan of going off on scenic walks during the day and good food and drink in the evenings. Yes, we're basically middle aged
You'll never meet a more enlightened group of guys in your life. I think. One of the guys recently said, after having seeing a comedy routine on the subject, that he didn't "get" how identifying as a different gender "works". Which was the first time I think anything trans related had ever come up in conversation and was a bit of a surprise. In contrast one of the guys, who's a big-wig at his company, is a (straight) LGBTQ advocate.
I want to come out to my oldest, dearest friends because if I can't be myself with them, who can I? Though I currently only dress in private - I've never been out in public before - I think this could be the nicest, safest first time for me. And I'd be in a place where the only people who know me are them.
I was thinking of having "the conversation" with them during the day while out walking, which should be a private enough setting for it. I feel a bit nervous because I've been dressing since we were teenagers but have kept it from them... it's wierd because it feels like it could be a hard conversation to start, but they're my closest friends and I know we can talk about anything. After the reveal I thought I'd suggest that I might turn up for dinner wearing clothes that I feel more comfortable in and leave it at that.
I'm pretty sure their first immediate response will be laughter, but that's ok. If any of them told me something about themselves that was completely unexpected I think I'd laugh first - and that's exactly the kind of friendship we have, we laugh about everything. So I imagine I'll tell them, there'll be a laugh and maybe some jokey questions about bra sizes or some such and the conversation'll be over until the evening.
I'm 100% sure that nobody will object to what clothes I wear for dinner.
I've already decided what I want to wear - I've got a favourite long sleeve top which looks good with or without a bra. I don't want to overload them for my first time so think I'll go bra-less. My favourite boot-cut high waisted jeans go lovely with that top. Then my cat-eye glasses (in contrast to my men's letterbox type spectacles) with some subtle eye makeup - eyebrows, liner and a little mascara. I've never been a fan of heavy makeup! I've just started growing my hair but it won't be particularly long by then, and I'm not going to wear a wig - rather I'll just see what I can do with it when the time comes.
I'm positive it won't change anything between us, but I'm still a bit nervous.
I still need to run this past my wife - she's the only person who knows so far and although she's been completely supportive I'm not sure whether she'd want my first time in public to be with her or not.
Does anyone have stories of how they came out to their closest friends they'd like to share?
I plan to post back to this thread after the event with how it went, if anyone's interested.