The best way to tell someone?

[Briana90802]

So maybe you want to tell your friend or coworker that you're a crossdresser. What is the best way? Or should I ask what is it that you have told others? And I'm not talking about your SO. Friends or coworks.

[Angela Campbell]

The first thing I would do is determine if there is a need or reason they need to know. If you are not sure what to say and how to tell them is it possible they are not close enough for them to need to know?

[linda allen]

Why do you want to tell them? As almostalady posted, do they need to know?

There's no one "best way" to tell someone you are a crossdresser. It depends on you, your friend, your relationship with that friend, circumstances, etc.

You could sit them down, tell them you have something to tell them, and then say "I just thought you should know I'm a crossdresser." That's one way.

Another would be to just wait for the appropriate situation. Say you two are watching a movie and there's a crossdresser in it or you're in a restaurant or other public place and your friend comments on the crossdresser. You could say "Yea, I am one of those too."

Or you could just whip out a photo album of you dressed and say "Do you want to see photos of me dressed as a woman?"

There are dozens of ways, you have to pick what seems right for you.

[BLUE ORCHID]

Hi Briana, It's on a need to know basis.

[Carla Stevens]

I don't think there is a right or wrong way. Only you will know how, depending on who you are telling.
I told my best mate about Carla last November. He has told his wife as they don't keep secrets & I was happy for him to tell her.
I was having 'issues' with stress & depression at the time & part of the problem could be put down to my Gender Issues. Bottling up all those feelings & emotions for so long was getting to me.
I had to share it with someone I knew, not just other CD'ers.
I'd planned what I wanted to say to him, but when it came down to it I really struggled & burst into tears infront of him. I struggled to get it out, all I'd planned to say went out of the window & I managed to say him "There is another side to me that no one knows about & she's called Carla". I was extremely emotional.
He was suprised, but not shocked.
We chatted & he asked me questions & I told him a little about how I felt etc.
All I can say is that it was such a relief to share this with someone & for them to be understanding & supportive.
I guess I already knew he'd be alright with this, but it didn't make it any easier telling him.

[Stevie]

First there has to be a need to tell someone. I would find a way to bring up the subject and see how they respond to jokes or just dressing in general. Then if felt comfortable with their answers you go from there.
I have personally tried this and without them ever catching on got them to express their real opinions which was rather disturbing to me. So I concluded not to say anything to anyone. They might sound supporting but when you ask them a direct personal question about it they express a very different view point.
Look at the ones that told their wives. Something told us that they will be supportive but when it hits home they sing a different toon.

[Beverley Sims]

It is so easy to share dressing with strangers than those close to you.
I do not want feedback so the only ones that find out are desk clerks and shop assistants.

[PaulaQ]

I told my best mate about Carla last November. He has told his wife as they don't keep secrets & I was happy for him to tell her.

"Three can keep a secret - if two of them are dead."
- Ben Franklin

[Lorileah]

I have told many friends. I have even just showed up someplace as a way of coming out. Would not advise the latter unless you are really positive that the friend is accepting. Almost exactly one year ago I walked into a bar where my friends were. Maybe two or three already know but the other 10-12 or so didn't. Result? Everyone loved it and they now expect Lori . But I would never have done that without knowing that most of them had no problem with it.

Usually when I tell someone new (which now is rarely) I either just say "Hey, guess what?" or I say "See this photo???"

[wilt575]

First there has to be a need to tell someone. I would find a way to bring up the subject and see how they respond to jokes or just dressing in general. Then if felt comfortable with their answers you go from there.
I have personally tried this and without them ever catching on got them to express their real opinions which was rather disturbing to me. So I concluded not to say anything to anyone. They might sound supporting but when you ask them a direct personal question about it they express a very different view point.
Look at the ones that told their wives. Something told us that they will be supportive but when it hits home they sing a different toon.

I'm not one to just come out with it, as far as those you want to of feel comfortabe with knowing. I just give a subtle hint, like wearing something fem but not overly fem. Something like sweater or tee, girl cut jeans (not overly bling) even wore fitted shirt once.Then wait and see if they react or comment, then go slow, don't say to much just be relaxed, don't be defensive.

[Joanne f]

I personally think that it is best not to directly tell anyone just let them come to their own conclusions and then answer them if they ask anything but it might be wise sometimes to mention it if you are expecting someone to see you in a dress for the first time and they have no idea as to what you are like , which is a bit ironic coming from me after the way I done it

[Genifer Teal]

I would speak positively about it and not be the least bit ashamed. Talk to them as if they are eager to learn more about this special trait of yours. The whole feel like a girl thing might be easier for someone to accept than trying to explain underdressing. Don't talk it down by saying, I only do this or I never do that. If you are telling a woman, use it as a way to connect with them on things they deal with every day. Let them know you will aswer any questions they may have. Don't rush them into deciding how they feel. Give them time to process this new information.

[GinaD]

I was at lunch with a female friend i worked with and she brought up the topic of crossdressing. She had a few other friends who she would occasionally meet who crossdressed. I didn't let on I had been doing the same since my pre-teen years but it got me thinking. So we planned to meet for a few drinks. I showed up fully made up in my favorite black mini skirt and heels and my favorite long wig. She was standing outside waiting for me and I just walked up to her and greated her like normal. It took her a few seconds to realize it was me, then she started cracking up. She gave me some great compliments and we had a "girls" night out. She playfully talked smack if I got more attention than she did. It worked out great.

[NicoleScott]

The best way to tell is something you'll have to figure out, as there are factors we can't possible know about. But I think the worst way is to show up en femme.

[Aylineira]

I agree with another poster that you should weigh the reasons why you are doing it. Remember that if you tell one person, almost certainly another person could find out and then another within that circle. Just be as prepared as possible.

[Briana90802]

Well I guess what I'm looking for is a good way of approaching it. What conversations should I have that help bring the topic to a front?

[Cheryl T]

Except for my wife I have only told one other person. This was someone who I was very close to years ago and when we reconnected I wanted to tell her. While she didn't judge me or react negatively she did surprise me by making her first question..."Have you had sex with a man?".
It appears that no matter how close we are to someone and how well they know us the sexual component is what they perceive to be the prime motivator.

How to tell someone? I don't know that there is a truly GOOD way to do it. Each person will react in their own way and I think that we must tailor our discussion to that person at that time and not search for some generic method of broaching the subject.