When to tell her?

[Jill]

This question came to my mind because of my thread, "some friend" because the "friend" featured in that post told me that I should tell a woman that I crossdress on the first date or earlier, basically, right when I meet her. I don't think that's a good time frame, especially when you're talking about dating very conservative women.

So what does everyone else think? When you meet a woman, when is a good time to tell her?

[Sigrid Cutie]

Hi Jill.
well i can only talk by my experience, and i didn't told my SO i crossdress untill after 2 years of marriage, and after a few conflictive months we kept talking about it, and answering every question she had she accepting and all, now a few months ago i told her that i wanted or needed to transition, again after a bit of time for her to accept this fact, i ask her if i would have told her before we had a good loving, stable relationship woud you have accepted me as crossdresser and now as a TG, and her answer was NO. but like we build a great relationship and love, she is able to accept it now.

it is very important to be truthfull to your other half about it when she asks all kinds of questions.

by this i don't mean it will happend to every one this is just my very particulat case.

well i hope this helps you a bit.

[Melinda G]

How many women do we date only once or twice, and find there is nothing there? Do you really want a dozen or more women running around telling the world you are a crosdresser? I don't.

And how about all those women you date a few times, and it doesn't work out. Some of them get kind of angry when you stop calling.

[TSchapes]

I don't think this is required on the first date since you are more than your gender(s). I advise people to tell before you get serious in your relationship, especially before you are married. This I say to CD's.

I also believe if you might suspect that you are heading for transition or wanting to be TG 24/7 that definitely needs to be explored prior to dating. Maybe that's a controversial stand, but I know I wish I had counseling prior to being married.

-Tracy

P.S. I'm a fine one to talk, my first date with my wife of almost 20 years was on Halloween and I went out with her dressed as Elvira. I still had to explain to her months later (when things started getting serious) that I was a CD.

[Karren H]

There's only two answers for me.. Either the first date. Or if you didn't on the first date..... never..

[PretzelGirl]

There's only two answers for me.. Either the first date. Or if you didn't on the first date..... never..

I find that an interesting answer. Don't you think that human nature would take hold and they would always run on the first date? My assumption (and this is a hard thing to really know) is that unless a woman is into CDs, there never would be a second date because you haven't developed the relationship to the point where they think "he is the one I want and the CDing is just something that comes with him".

How well do you know someone on a first date and if there are any signs of something out of the ordinary, doesn't that most often keep a second date from happening?

[Sheila]

From a GG viewpoint, as soon as ytou think this is leading somewhere, will be different for every relationship, but well before she falls in love with you hun, nowt like feeling you have been played for a fool if you leave it way too late :sad:

[cindym5_04]

I wouldn't tell her on the first date. That's just way too soon. You should definitely wait to see if it's going somewhere, then tell her before it gets TOO involved.

[BarbiB]

During the first post coital cigarette break, would seem to be about right.

[JulieC]

Somewhat agreed with Sheila.

I think first date is too soon. If you're looking for a spouse, the reason you date people is to get to know them before getting engaged. Getting to know them doesn't mean one date, and that's it. To me, one date is to see if there's mutual attraction, enough to warrant having another date and learning more about the person.

There's a zillion things I've learned about my wife after I married her. You just can't know everything about a person, try as you might. In dating, you try to learn about the biggies that you know would affect your ability to be with that person in the long run.

With crossdressing, it's a bit reversed. I knew, and many of you know, that crossdressing is something a prospective spouse needs to know about. It might not be something she thinks to ask; it's just not that common. But, it can affect her decision to be with you.

I don't know precisely when the right time is, but for me it was when things were obviously serious and to spend any more time on the relationship was wasting her time and mine if she didn't accept me as a crossdresser. I wasn't 20 anymore, and the prospect of wasting years on a dead end relationship wasn't something I was willing to accept.

So, I told her after a few months of dating. She didn't run screaming for the hills, accepted it, and bought me pantyhose a couple of days later (I'd purged, because I didn't want her to find out on her own, but on my terms).

[Shikyo]

There is no need to tell the girl straight away. The best would be to wait until both of you feel like there might be more behind this relationship. The moment of time when you are starting to become serious about the whole relationship is when you should reveal the secret of crossdressing. Earlier than that I do not think it's necessary just because at that point of time you are not sure if you really want to continue the whole relationship or if it is already over.

By telling her your secret you will also show her that you really trust her and you are really serious about the whole situation. This should give a nice start for a serious relationship, but you have to be careful how and in what kind of situation you tell about it to her. It would be very helpful if you are ready to answer any questions about it after you have told her. Also you should give her some time to get adjusted to the matter as it is quite a shock for someone who is not used to matters like this.

[DonnaT]

IMHO, you should tell when things start to become a touch more serious than one or two dates. Like when you begin to think it may turn into a longish relationship.

No need to wait longer than that. If you do, and she bails, then you'll have wasted time you/she could have spent finding another GF/BF.

[Ralph]

This question came to my mind because of my thread, "some friend" because the "friend" featured in that post told me that I should tell a woman that I crossdress on the first date or earlier, basically, right when I meet her.

Good grief, no. I'm all for making sure the person you marry knows exactly what she's getting in the package, but I wouldn't advocate outing yourself until you have a good idea that this could turn into a lifetime commitment.

You start sharing potentially damaging secrets when there is a level of trust that goes beyond casual friendship... when you're fairly certain she won't use your information as a weapon against you.

I would no more tell a first date that I'm a crossdresser any more than I would tell her I pick my nose when I think nobody is watching, or I snore like a freight train, or I voted for one politician or another. There's a time to make a good first impression, and a time to start exploring each other in more detail.

ralph

[Sophia de la luz]

Well, if crossdressing is "inner demons lite", that is to say, you have much nastier stuff inside, underneath the gender issues, then maybe talking about your clothing/gender identity issues would qualify as "small talk". If not, if in fact the crossdressing is a deep concern, akin to being molested as a child, please spare the world your drama circus, and wait until you have them in your clutches and they can't get away... because they "love" you.

[Di]

I think it is best after you think things are getting serious she already knows you and you know her.

[Jessica Who]

I told two girlfriends, one of whom ended up becoming my wife. Both of them were informed of Jessica about one month into the relationship; I think that the first date is way too soon, unless crossdressing is something that she brings up and is enthusiastic about, which would probably be extremely rare.

[Gabrielle Hermosa]

...especially when you're talking about dating very conservative women.

So what does everyone else think? When you meet a woman, when is a good time to tell her?

I think the sooner you can tell her, the better.

It's tricky, no doubt about it - especially if conservative women are all you have to choose from. The chance that their minds have already been filled with the lies, cliches, and misconceptions about us is probably higher among the conservative bunch.

I'd say you need to either tell her, or terminate the relationship (if you feel you can't tell her for whatever reason) as soon as you begin to feel as if she's long term material. One can usually tell fairly on in the relationship if that is the case. TRUST and RESPECT have a lot to do with that.

If you believe you can trust her and that she respects you, sit her down and let her know about your prettier side. When you tell her, be sure to let her know it is a beautiful gift and NOT some condition or affliction you suffer from. How you tell her will directly affect (to some extent) how she takes the news.

The rest is up to you. She may need time to digest it, or may immediately let you know whether or not it is a relationship killer or a relationship strengthener. As I'm sure you already know - do not waste your time with a woman who cannot love ALL of you. It's not fair to you, or her. If she needs a 100% masculine man - let her find one. Trust me when I tell you that there are plenty of women who would actually prefer to be with a crossdressing man. Do not settle for anything less. Not always easy to find them, but if you don't "settle", you WILL end up with one. :)

[ReineD]

I agree with not telling on the first date. Wait to see first if it is going anywhere. If you date a few times and realize you do not wish to see each other anymore, what would have been the point of telling her?

Now if you do decide to continue seeing each other, either romantically or if you discover there are no sparks but you both agree you would like to be platonic friends, then by all means reveal who you are.

Very few people reveal their complete life histories, issues, etc. on the first date. Trust, born out of mutual caring, needs to grow before you should share your more vulnerable inner selves. This takes time.
:hugs:

[julie w]

I told my ex about 20yrs into the marriage I though she was ok with it but
she wasnt
I told my SO of 8 years about a month or two into our relationship she
knew something was going on , and kept asking , I guess she thought
It was worth putting up with to keep me, we are still together
The most important thing if you are planing to tell ( which only you can
decide ) is that you dont let her meet your work or personal friends as
if it goes badly ,you could find yourself outted
as you can bet your bottom dollar that she will tell all her friends if she doesn,t. approve
If you dont care then nothing to worry about

[sissystephanie]

I told my dear late wife when I asked her to marry me. BUT, I had known her for about 15 years at that time. We grew up together! She had actually seen me wearing my older sisters clothes as a young boy! My grandma sometimes dressed me that way to play, so I wouldn't ruin my school clothes. Of course, I didn't mind at all!!:heehee:

First date with a new GF? No way, Jose! Not unless you knew right off the bat that this is the woman you wanted to spend the rest of your life with, which is highly unlikely. The only one you should think of telling is the one you plan on spending your life with. And in the interest of all concerned, when you do find that one person, do tell her upfront and in full. Honesty is always the best policy, because she will find out sooner or later!!

[WandaRae2009]

I agree with Melinda G. It could be dangerous to tell somone before you know them well and have gained trust in that they would keep such information private if you are not out publicly, especially if that person may out you where it could cause you to loose a job or something critical.

[Jilmac]

I can only speak for myself but I told both my first and second wives about my dressing while we were dating. It was probably around the fourth or fifth date that I mentioned anything about crossdressing. I wanted to be as honest as I could but my honesty backfired because neither one approved and I stayed in the closet for many years.

After my second wife passed away, I met a woman who is now mt SO. I told her about my dressing, again around the fourth or fifth date. Up to now she has been very supportive although she prefers not to ever see me dressed. I am ok with that because I'm not hiding it anymore. I honestly don't know if there is a right time to tell a person whom you are dating that you are a crossdresser, all you can do is take your chances and hope for the best.

[Bobbi Lynn]

During the first post coital cigarette break, would seem to be about right.

What if neither one of you smoke??

[TSchapes]

I would also hesitate to actively look for someone that is into CDs, because that maybe the only thing they like about you! For me anyway, there should be more to the relationship than the CDing. This is another reason to hold off from the start... IMHO.

-Tracy

[cdbrandi]

I told my wife on our 2nd date because I did not want to invest the time if she was unwilling to accept all of me.

[Dana Lane]

Personally I think it depends on how important it is to you. The longer you wait the harder it is. If it is a new relationship I think it would be much better to try and expose her to that lifestyle in some way shape or form. Mention a latest court ruling or some kind of news article and see what her response is. If she pops right out as anti-whatyouare right off the bat move on. If not, hang around a bit and decide a bit later.

If being with a partner that accepts you for what you are entirely then make sure that is considered very early in the relationship.

[BarbiB]

What if neither one of you smoke??

I was speaking figuratively. To put it another way....

While basking in the afterglow of consummating a perfect enduring friendship.
"If it flies away it was never yours"...
"If it stays it was always meant to be so" ...

Either way, you will at least have been laid one more time.

[AKAMichelle]

I personally think you should get connected to the woman in a personal way before telling her. Sometime after you develop a friendship but before sleeping with them.

I have told several conservative women and some accepted and others ignored it. My wife is the only person that I didn't tell and she is the only one who totally flipped out