How to tell a lifelong friend?

[prettytoes]

There are very few people who know of my crossdressing. My wife, and a close friend who was a female impersonator years ago are the only ones I have told. I have a female friend that I have known all my life (lets just say it's over 45 years!). I guess an important bit of information to add is that she's gay. I am going on a vacation with her, her brother (who is also a lifelong friend), and his 13 yr old son. She and I are leaving a day in advance of her brother and his son, due to flight availability (I just hate to have to spend an extra day on a tropical island...darn airlines! lol).
I really want to let her in on my secret, but I'm not sure how to even approach the issue. I know she will be OK with it, I just don't know how to start the conversation. Do I just blurt out "I wear women's clothes"? Maybe I could just appear the first night in my bright pink Looney Tunes pajamas and say "guess what"?
I now understand how difficult it was for her to tell me she was gay so many years ago. I do not want to reveal it to her brother, just her. Her brother and I drifted apart for a while, but are now reconnecting due to a common interest his son and I share...scuba diving. The trip we are going on is a dive trip, and will be their first.
I will have time to tell her the first night, before the others arrive. Any suggestions would be appreciated to help me approach a conversation that will be difficult for me.

[Katy120]

It seems to me that all elements required for a good conversation are already in place. Perhaps you could use the memory of her conversation about her secret many years ago as the springboard for telling your secret.

[Marcelle]

Hi there,

I am going to start with a few questions for you . . . "Do you have an absolute need to tell your friend?" If so, can you live with others knowing? The reason I always start with these questions is that once the information is out to others . . . you can't undo it and you loose control of that information. Good friends may have a deep desire to share that information with others in order to process it, it is not facetious it is just human nature for some. In my case I have told friends but then I don't care who knows as I prefer to be able to be me around others boy or girl.

Now to your question. If you have the time, I would approach your friend and tell her you want to discuss something important before the others arrive. Perhaps over some coffee/wine or whatever. In my case I simply told my friends I am "trans" and then went on to explain what that means (CDing, not TS, straight etc.). I find there is no real way to slowly introduce this into a conversation so I set the stage "I have something both personal and important to discuss" then have at it. When I am done, I let the person process and wait for questions. After question period, I ask them if we are "okay". If you want discretion, you may want to add "I need you to keep this between us for now".

The one thing I will add is that if you even think this could go bad or awkward, I would not use a fun time trip to come out as it could spoil you whole vacation. Perhaps save it for after the vacation if you think this may occur.

Hope this helps and good luck.

Isha

[kimdl93]

I think after all these years of friendship, and in light of her candor about her sexual orientation, you're entitled to share this core aspect of yourself with your friend. With a day extra, just arrange for a quiet lunch or a picnic on the beach...someplace where you can talk freely. Preface your reveal as you wish, but it might as well be simple and to the point...something like "I've something I need to share with you. It's nothing bad, at least I don't think so. But here it is...." Then let the conversation take its course.

[Rhonda Jean]

I think a big coming out statement is unnecessary. Why not just reveal a bit of it and answer her questions as they come. I mean, you're going on a tropical vacation. Seems pretty obvious you'd at least want to get a pedi and wear a tropical color on your toes. If you wear earrings, wear hoops or dangles. A sarong is certainly appropriate, and a sarong with flip flops and polished toes with shaved legs will probably at least cause her to comment. Seems like "I have a bit of a girlie side" would be enough of a coming out statement then. And I wouldn't worry a bit about her brother and his son. You won't be the only guy down there in a sarong with shaved legs and painted toes. You're on vacation. You're entitled to let your hair down a bit.

Like Isha said, though. You have no control over what anybody does with that information. You're one Facebook post from everybody knowing whatever she knows. If you do as I suggest, you can bet there'll be a picture on somebody's Facebook. Being a vacation photo, I don't think it'd be a big deal.

[Robynts]

I recently came out about Robyn to a dear friend. The context of the discussion was that my daughter has decided, after knowing about Robyn for many years, that Robyn is bad (evil, sinful and all that crap) and if she stops talking to me that will cure me.

Anyhow, I told my friend that "this is the issue" and showed her a picture of Robyn on my phone. Her first question was "who is she?" I explained that it was me.

She was very accepting and has mentioned going out for lunch together.'

The point of this was that I found the smart phone pictures to be a great way to break the ice for the conversation about Robyn.

P.S. my gills are drying up! I have not been diving in the tropics in several years. I am soooo jealous.

[Beverley Sims]

Talk about your acceptance of her being gay and then tell her you have an associated secret that you would like to share with her.

[Tracii G]

+1 Beverley makes a good point with the acceptance angle.
I hooked up with an old friend of 30+ years and I just came out and told her.
She had all the normal questions so I answered truthfully and to the point. She has many close gay friends and me being trans was a non issue.
If this person has known you for many years I think she will see that you are the same person.

[Stephanie47]

I absolutely do NOT know why it is necessary to tell a secret of this nature to someone and burden them with the responsibility of keeping it. What is there for her to gain with this knowledge? It's not just this thread. There are many threads I've read echoing this issue. I just do not understand why anyone needs to 'out' themselves to others. For whose benefit? What will this knowledge lead to? Any expectations on your part?

Why do you feel it is necessary to share this secret with her?

[prettytoes]

Thanks for all the replies! I'm positive she will be okay with it; we have always been very close.
I really don't want to come out to anyone else, I just feel that I want her to know. My legs have been smooth for 3 years now and I never had any comments about it at all. I have become friends with many of the resort's staff (this will be my eighth trip there in 5 years) and I do not see a need to share this side of myself with any of them. I'm quite sure she will keep this between us, we have shared secrets in the past that have always stayed between us.
Robyn, sounds like you need some nitrogen therapy! Nothing helps all my aches and pains like a week of breathing nitrox! I usually do 25-30 dives in a week at the resort I go to. It does a body good!

[effemin8]

If you tell her early on you can then spend the time before the others arrive dressed how you want to be, not how you think you should for them! Above all have a lovely time.

[KaceyR]

If you are thinking it will be easy for the friend to accept then it should be OK..
As long as you've really analyzed the person well. (And it probably helps because
of her alternative life to begin with).
I can see the fact that with several 'coming out' stories it can be a bit like the 'Pink
Fog' which can cloud judgement and the CDer can get _too_ impatient or rush to
tell everyone in the world. But only you can judge. So if it's seeming good and you've
Done heavy thinking (not rushed to judgement) and feel it'll be ok to involve them
with your CD life then that's great and I wish you great success...
(And a great trip too :) )

I just successfully came out to my best friends myself today actually.
It went well... Although it actually took a bit of time to finally do it.
I had wanted to for awhile, but then after a couple visits and 'aborting the mission',
I then rethought better hold off until I told my mom about it and figure from there.
So had Xmas where I told my mom (that went well) then with some anxiety still I didn't
bring it up on New Years with the friends. But I finally did today.
Was easy once I got started, (and had figured they were suspicious to begin with).
For my friends it was somewhat easy because the one had mentioned about "unless
Your hiding a secret life" statement a month ago which I didn't respond to back then...
So I just stated that there was something I wanted to talk to them about... You know back
when you said... :). Then I held up Kacey's pic on my iPad and said "meet Kacey" :)
So that intro was pretty much already set.
so now at least most friends and family now know (a few are not so progressive so didn't plan
To tell those) and I don't have to 'hide' from them at least.
Basically they're the ones that might stop over sometime.. So if they do, and Kacey's
home it won't matter. :) none of my friends are ones that really would call up and say 'let's
go do something' though, so I doubt they'll be that really help me push the envelope as
Kacey (unfortunately) but I wanted to set things straight with them.

For your friend, it may be more of the way I told my Mom..
Just said outright, "there was something serious I needed to talk to you about..."
And then just got into it leading with info about how long, and so forth.
I still took it easy and just gauged her reaction, and let her ask whatever without
plowing thru the info full speed, which might cause her panic or unease.

Anyways, good luck and good trip! I envy your trip...such an awful place those
tropical islands are. And here were coming up to balmy 0-degree high (f) weather....
Just don't know why you'd want to go down there :). LOL

[LaraPeterson]

Pretty Toes, first of all--good luck to you whatever you decide to do.

I understand Stephanie's POV and I've wondered myself why I want to tell people who would otherwise never have a need to know and might never find out. On the other hand, the reason for wanting to tell, at least in my case, is because I care deeply for the person(s) who I share this with. In fact, I just posted a reply about telling my own sister on another thread.

It sounds like you have several things going in your favor with your gay girlfriend--so I'm going to throw in my two cents about how I'd "tell" her. Make yourself pretty and walk in the room! First, she's not going to be as surprised as you think and second, she's going to be really excited for you.

Just be aware that what Isha wrote is always going to be true. Once the cat is out of the bag with anyone, it's gonna meow loudly.

[I Am Paula]

Just remember the golden rule of coming out. It is not your friend who will gossip this all over, it's the blabbermouth people she tells who will.