When should I tell my girlfriend....

[Amy R Lynn]

I'm certain this topic has been covered in here before, but I can't seem to be able to find a thread that addresses this. There are plenty of "How To" threads, but I think the "when" is pretty important too.

I have been dating a girl for about a month now. I have done some internet research on the subject of when should I spill my feminine secret, but have not come up with very good sugesstions. I have seen in some posts that it would be best to tell her early on, and others have stated that its best to wait. I don't want to wait too long. I don't think it would be good to wait until we are engaged and suprise her with Amy. However, I don't want to tell her too soon and scare her off. I plan on having a heart to heart with her. I just need to time it right. I am fully prepared to accept the possibility that she may reject me, but its better than being divorced.

I am aware that every situation will be different, but I would love to hear the communities sugesstions here. How do you know when the time is right to tell her about this?

[prene]

This is a hard question.

I have lost 95% of my girlfriends over this.

I have always told them to early and to late in the relationship.

[Melissa Jill]

Probably about 2 weeks ago. She's either going to be accepting or not. Putting it off it just going to delay the inevitable whatever that may be.

[ronda]

i think that most wait till they are sure that they in a serious relationship and that you can trust the person you are with not to out you to people that you can not afford to know such as some employers but do it as soon as you think it is important to let her know so she can make up her own mind that she can handle your cding.good luck Hugs Ronda

[Diana Bain]

Only you can tell when the time is right. I can only tell you from my perspective...I'd been dating her for about a month, I felt compelled to tell her...though we've had tough times in the past...I'm now considered her girlfriend...18 years married this October. Good luck, but don't wait to long.

[Alice B]

I have always said the sooner the better. If it is going to be a deal breaker it should be before emotions get too involved. If she proves to be accepting it will lead to a stronger bond. You have to be fair to her and yourself.

[sissystephanie]

Amy, I told my late wife when I proposed to her! She did ask me some questions, mainly concerning how far I wanted to go with crossdressing as a female. I told her that I only wanted to wear feminine clothing, but did not want to actually become a female. I wanted to be her male!! she accepted that and we were married for almost 50 years before cancer took her.

I have always believed in honesty, and felt then and still do that hiding something from the person who may become your wife is not proper. Unless of course it relates to a gift of some sort! The timing of telling her is totally up to you, but the longer you wait the harder it will be. I started crossdressing when I was 6 years old and met my wife to be when I was 9. So I did put it off for some years, but when I decided that she was the right one for me I told her! You are coreect, it is better to be rejected than to be divorced!! I say, tell her!!

[Beverley Sims]

Get the relationship on a reasonably firm grounding and then tell her.
Consider the worst case scenario and find the Right time, not necessarily on a dinner date or some romantic situation.
Tell her before you both get too serious, you can test the water carefully by asking her views on alternative lifestyles.
Try to be tactful and sympathetic towards her.
I consider you have about a 20 percent success rate.
If you wish to continue dressing, "You have to tell her".
All the best in your relationship and keep researching the subject and take note of what others will advise you.

To Prene. I don't think you have told them too early or too late. They did not want any part of it or did not understand.
What about the other five percent?:)

[Kayla C]

You should tell her when you believe you are heading for a long-term relationship. But you should also brace yourself for the strong possibility you may lose her. Kelli is right - if she rejects you she is not the girl for you. But making a long-term commitment without her knowing is looking for grief down the road, especially if she discovers this on her own. As you'll see from other threads, it's usually the perceived hiding and deceit later on that creates problems, not the crossdressing itself.

[bridgetta]

immediatly.. also.. ask your self if she is the kind to understand or not..

[cyndigurl45]

I had an unusual set of circumstances I had to tell one of my girlfriends I was a guy, we meet in a gay bar, I hung out there they were accepting as most gay bars are......

[kimdl93]

A month isn't very long. Have you known her for some time before you started dating? Have you learned anything about her attitudes towards transgendered people?

I don't think its so much a question of days or weeks, but rather how well you know her and how serious you are about a long term relationship.

[UNDERDRESSER]

Sigh.

I'm in this situation now, or I hope I will be. I've been "seeing" this girl for 2 months now? We aren't...dating as such. She has issues to work through, but I know she likes me, and I'm prepared to give her as long as it takes. I KNOW, this one is going to be for the long haul, serious keeper.

I'm working up my nerve to tell her soon. I think a decision point is approaching for her. Our conversations are almost painfully honest, subjects covered at this point, are ones you don't normally get into before physical intimacy, or at least when you are somewhere on the field if not yet having scored a home run, to use a common phrase.

I've thought about just burying this part of me, and just pretending. it would mean a total purge and shopping for expensive mens briefs. Don't think it would work. The subject of crossdressing was raised yesterday, I jokingly suggested wearing a skirt to work to be cooler, her response was jocular, and suggested I pass it off as a Summer kilt. etc


The stress of holding this back from her is beginning to tell. I don't WANT to be dishonest with her.

My view is tell her, in a controlled manner, in an appropriate setting. I have NO idea what her response will be, this is just my opinion.

[JamieQ]

Now! If you loose her over this then wait until you can get one that will accept it, life would be MUCH more easier! I know its hard to let some go....:)Amanda

[Ayame]

In my opinion the best time is before you are dating. There are lots of open minded people that don't care. So its not worth investing months or years into a gamble of whether or not someone will accept you from waiting to tell.

[JamieQ]

In my opinion the best time is before you are dating. There are lots of open minded people that don't care. So its not worth investing months or years into a gamble of whether or not someone will accept you from waiting to tell.



Ayame, you said it the best! BTW I do know what it feels like to let a girlfriend go, but surely it would be worth the wait for one who is accepting? Would it not?

[Sandra]

Coming from a GG......Do not leave it until things get serious, if you do then she may feel that she cannot trust you and will probably question everything that you say to her.

[max]

Tell her soon, that way if she doesn't really love YOU for YOU then you can start moving on.

[Engendered]

The sooner, the better. It will get much harder as time goes on. Good luck! :)

[mikiSJ]

I would suggest you tell her as soon as you feel confident that she won't go running down the street telling everyone your "secret" and also as soon as you feel there is something there in the relationship. Each relationship is different, but it is up to you to screw up the courage to share your "secret". If this relationship fails because of your "secret", keep trying and trying and trying.

My first marriage was on the rocks for a couple of years, but when I told her, that was the proverbial "straw". I was very up front during my next intense relation. She was accepting and the relationship failed because she was on the rebound from a failed marriage.

I told my current wife the same night I proposed to her. I trusted her confidence, I trusted her "openness" and I suggested she talk with a counselor she had been seeing previously. The counselor was a very European Dutch man who gave her reading material and "acceptance" of her choice to marry me. That was 37 years ago and I still share part of her closet.

[reb.femme]

A month isn't very long. Have you known her for some time before you started dating? Have you learned anything about her attitudes towards transgendered people?

I don't think its so much a question of days or weeks, but rather how well you know her and how serious you are about a long term relationship.

Hi Amy,

I totally agree with the above.
Posts have often mentioned sounding her out for TG/TS/CD feelings too, so why tell if she is heavily against? Maybe then, better to find a way out before anyone gets hurt.

A little simplistic in short but surely this consideration must be weighed up first.
Hopefully, if she is at least sympathetic, then you have a basis upon which to advance.

Rebecca x


I

[Msora]

I am an avid reader of Dan Savage's weekly sex advice column. He gives six months as a deadline for when you should disclose any potentially deal-breaking kinks. Basically, she needs to know you well enough to be willing to try it, but before any long term commitments are made. I don't have any experience using this guideline, but it seems well-reasoned.

Also, I know that CDing isn't really a kink, but it's similar enough from the SO's perspective in this case.

[Lorileah]

Coming from a GG......Do not leave it until things get serious, if you do then she may feel that she cannot trust you and will probably question everything that you say to her.

and there you have it. I have said many times that there is equity you build in a relationship. the longer the relationship the more equity. When you wait then you start to have things that you didn't before. Feelings get stronger and thus the hurt gets deeper. People resent it when you waste their time. They resent it even more when they believe they have a solid relationship with you. You want to see a hurt look? Wait until your GF thinks that everything is sunshine and roses, That you ride a white charger. Then tell her. Watch the look of confusion and then hurt. You are building trust. Think of trust as a huge wall (or tower) and you pull the lynchpin block out. If that wall is only two layers high, you are disapponted but you say, "hey that isn't much to rebuild" If that wall is 50 layers and you pull that brick, then you watch as everything you have worked for crumbles. Some will rebuild from this, some will rebuild better. Most will walk away shaking theitr heads and mumbling.

Continuing the analogy, you tell her early in the building process, you can make sure that brick is in there solid. That if it is a problem you can either work around it or make it stronger.

It may or may not be an issue but really wouldn't you want to know earlier so you can move on if needed?

[Jenniferathome]

There is a point in every relationship where you go from dates, to dating. We all have a feel for when the change happened. That point where it's serious. That is when.

[il.dso]

Always hard to give advice since there are some many variables at play.
Also, there never seems to be a perfectly "right time" to share such an important personal and private part of your life.
Regardless, please know that MANY if not all of us have gone through this at some time in our lives.
It's takes a lot of courage and is scary.
Fortunately, you have many friends here in cyberspace to help you along the way.

[Davena Doll]

Take her on a cross check. I mean take her to the mall gander at one of those cute dresses in the window and say "I wonder how I would look in something like that". hear what she says. At this point she thinks you will be joking. If she says somthing like "you better not dare", you know. If she says something like "lets find out" Its game on. NOTE if she is atracted to the loud, obnoxious, machismoed out, tatted up biker type, you dont stand a chance.

[Julie8181]

In my opinion the best time is before you are dating. There are lots of open minded people that don't care. So its not worth investing months or years into a gamble of whether or not someone will accept you from waiting to tell.

I agree 100%. You may need to put yourself out there in new social circles, but there are indeed open minded people.

[DebbieL]

Quite simply - the sooner the better. I put pictures of Debbie on my profile, along with pictures of Rex. I also included it in my description. It read something like:

I'm a cross between Robin Williams, Jim Carey, Bill Gates, Sean Connery, and Madonna. I'm as weird as Robin, as crazy as Jim, as Nerdy as Bill, a Geezer like Sean, and dress like Madonna.

900 women saw the profile, 10 expressed interest, six wanted dates, and one ended up being my wife.

Hopefully you've already given her some "clues" very early on. Both ears pierced with very visible CZ stones or loops, a woman's ring on your right hand, making comments on wardrobe including naming some designers, and using the proper terminology for various types of shoes. She's figured out that you're not gay because you're dating her, but she would know there is something different. She may even suspect, but she might be afraid of offending you.

Many women fantasize about feminizing a man, and if you have given her some kind of hints, she may just be waiting for you to come out with it.

Here's what you DON'T want to do. Wait until AFTER she has fallen completely in love with you, moved in with you, and maybe even married you, and THEN you tell her, and she feels like she HAS to accept it, but hopes it's just a "Phase", and you'll "grow out of it", then you assume that she's OK with it, have a couple of kids, get to where the youngest is in kindergarten and THEN she tells you she hates your dressing, hates you, and wants to marry her boyfriend who is a REAL MAN. Of course, you still have to pay child support, and day care, to her and her new husband, while her new husband physically and emotionally abuses your children. You'll ALMOST be free to dress and even transition if you want, but you will have to give up visitation.

Been there, done that, got the T-Shirt. I'd rather get No's from 150 women to get a REAL "YES". It was worth the effort.

[Amy R Lynn]

Wow, As always lots of great advice!

So a little more info to help here. She has some very close friends (males) who are gay and bisexual. She is very accepting of their life styles. To me this could mean a couple of things. Either she is just good being friends with them and wouldn't want to date them. Or she is accepting of an alternative life style in general. From everything that I have seen, I think she would be very accepting of this.

I think I'm going to wait for a couple more months just to make sure that she is someone that I could spend a long term relationship with. I suspet that she is. The tricky part about this is that it is a pandora box. Once you open the lid on this thing, there is no way to close it. Once this is out, its out. It can't be unsaid.

[UNDERDRESSER]

Quite simply - the sooner the better. I put pictures of Debbie on my profile, along with pictures of Rex. I also included it in my description. It read something like:

I'm a cross between Robin Williams, Jim Carey, Bill Gates, Sean Connery, and Madonna. I'm as weird as Robin, as crazy as Jim, as Nerdy as Bill, a Geezer like Sean, and dress like Madonna.

900 women saw the profile, 10 expressed interest, six wanted dates, and one ended up being my wife.

Hopefully you've already given her some "clues" very early on. Both ears pierced with very visible CZ stones or loops, a woman's ring on your right hand, making comments on wardrobe including naming some designers, and using the proper terminology for various types of shoes. She's figured out that you're not gay because you're dating her, but she would know there is something different. She may even suspect, but she might be afraid of offending you.

Many women fantasize about feminizing a man, and if you have given her some kind of hints, she may just be waiting for you to come out with it.

Here's what you DON'T want to do. Wait until AFTER she has fallen completely in love with you, moved in with you, and maybe even married you, and THEN you tell her, and she feels like she HAS to accept it, but hopes it's just a "Phase", and you'll "grow out of it", then you assume that she's OK with it, have a couple of kids, get to where the youngest is in kindergarten and THEN she tells you she hates your dressing, hates you, and wants to marry her boyfriend who is a REAL MAN. Of course, you still have to pay child support, and day care, to her and her new husband, while her new husband physically and emotionally abuses your children. You'll ALMOST be free to dress and even transition if you want, but you will have to give up visitation.

Been there, done that, got the T-Shirt. I'd rather get No's from 150 women to get a REAL "YES". It was worth the effort.I like this post. I have given "my" girl, some heavy hints. I've told her I'm more than a bit narcissist, I like, the idea of being a "sex object" as a man, ( true ) I shave my legs, I wore some outrageously bright bike shorts the other day, I've plainly stated I have a strong feminine side, ( also true, but not actually a lot to do with my CDing ) I said I was jealous about one of the other guys at work dressing up as hooker for Halloween. ( AT work, mind you! )

The response has not always been...enthusiastic, but there has been no withdrawal, and I'm pretty certain she still considers me a potential BF, once she has her own issues under control.

[Vickie_CDTV]

You need to tell before both of you put a large investment of emotional energy into the relationship and before you make any commitments. Ideally, you tell before the relationship gets serious, certainly before marriage, and most certainly before having children together.

[mscatie85]

In my opinion, one of the worst mistakes in telling someone about crossdressing is telling them too early in a relationship.

I would suggest you wait and tell them sometime 3-6 months after you started dating. By this point the initial awkwardness of getting to know someone should have gone away. This also give you an opportunity determine for yourself if this is the right person for you. Obviously if someone is not right for you, why would you tell them something so personal. Also since there is a little emotional investment from both sides, when you drop the bomb, your partner is less likely to cut and run.

When you do tell them, the key is to give yourself plenty of time to talk about it and always in person. Be prepared for plenty of questions, criticism of your gender, criticism of your sexuality and to be patient waiting for their final response (this may take days or weeks).

I hope this helps you.

[BRANDYJ]

Dating for one month? What does that mean? What, one date a week on Saturday night, or that you and her talk every day and see each other socially several times a week? One month is such a short time unless you sense that the chemistry is right for the BOTH of you. Have you BOTH committed to dating exclusively, or has that not been discussed yet?
I have more questions then advice at this very early stage of your "dating" this girl. My suggestion is to wait and see if she shows signs of wanting an exclusive relationship with you as much as you may want it exclusive with her. I'd also want to figure out just how accepting she is. You said she has bi and gay male friends, that's a hint. But the real question would be if she would ever consider a bi guy in a relationship and dating. Not that you are bi, but many women befriend bio and gay men, but those male friends remain in the "friend only zone" and are never considered for more then friendship. So as accepting as she is about her gay and bi male friends is a hint about how accepting she'd be for other alternate lifestyles,, but telling her to soon could land you in permanant "friend zone"
So without knowing if she is a serial dater or a girl seriously looking for something permanent, it's hard to give you any good advise. When it gets to the stage of you BOTH talking about dating and seeing each other exclusively because you BOTH are looking for someone for long term, then and only then, it's time to tell her.
In my past I only dated girls/women I knew I wanted something long term with, or why date them at all? I have never been one to date for the sake of a one or two night good time. Dating to me had a purpose, that was to potentially find the ONE and ONLY. Is this who she is to you? At this early stage. would you commit to her and would she commit to you? Give it a little more time and I think you will know when it's the right time. I wish you luck.

[Annie D]

The sooner you tell her about yourself, the sooner that you can start looking for another girlfriend OR the sooner you can start to develop a deeper relationship with her. Did anyone say "the sooner the better"? As you get older, the sooner you realize that the truth is ALWAYS better in a relationship than not telling the truth (I didn't say telling a lie), that you start to develop more trust and faith with one another. Omitting personal things about yourself is not lieing but it is not being truthful either.

[jillleanne]

Well first off, you mention 'one month' , 'engagement', and 'divorce' all in one paragraph. Not good. Therefore I will tell you, Monday evening at 7:23 pm is probably not the right time. Having said that, you might want to consider the following:

1. Has the , " Oh baby, Oh baby " feeling subsided yet?
2. Has she seen the inside of your house yet?
3. Has she mentioned she likes a guy with lots of chest hair?
4. Have either of you seen each other first thing in the morning yet? Did you recognize her? Did she recognize you? Did you/she remember her/your name?
These could be construed as signs necessary for a heart to heart.

I would suggest you just take your time, find out over more time if she could be the one, all the while putting out 'feelers' along the way, i.e, asking things like how do you feel about a certain type of people? You'll know when the time is right, just be patient as it will just come to you when it's ready in the not too distant future. The key for you is knowing she has a right to know who you are if she is to commit herself to you. and you already know that.

[Tracii G]

I told my current early on and she was fine with me being transgender.
I had been on a few dating sites and let it all out in my description and got lots of positive hits and had a few really good dates.

[Jacqueline Winona]

I think you have the right idea. Like Megan said, wait until you are pretty sure this is going somewhere. Having gay or bi friends may not mean that she wants a CD in a relationship, so work on the relationship first. I'm a big believer in timing is everything, and also think that you will know when it's time to talk about it.

[Amy R Lynn]

BrandyJ,
We have seen each other several times thoughout the week. So we have been on about a dozen or so dates. I agree that I don't think I want to let her in on this without knowing that she is someone that I would want to be with long term. I am looking for long term, but I have to know that she is one for a possible long term. I agree that it probably is still too early to figure that out.

I like the idea of putting out the feelers and seeing how she responds to some hypothetical situations. Like.,.. Did you ever consider dating (her bi friend). Or would you? I think those could be some good indicators prior to having a heart to heart about my femm secret. I really haven't given her many hints that there is a femm side to me yet. I don't shave my legs in the summer, and I haven't pierced my ears yet (would love to someday). So... I'll keep my feelers out for a little while more.

I also have to agree that I don't want to wait too long. I don't think a couple of months (4-6 months) would be too long.

GREAT ADVICE! I love all of the advice you can get in this forum. I would truly be lost without all of you!

[Annie D]

What if she told you tomorrow that she was bi-sexual and had a girlfriend that she has been seeing for the past 2 years? What if she told you 6 months from now that she ........ for the past 2 years? You can live with that in either scenerio, right?

What if,tomorrow, she told you that she had a sexually transmitted disease......what if she waited 6 months to tell you? It depends on each individual scenerio; a crossdressing boyfriend may be somewhere in the middle of those scenerios to her......best to find out where you are before you commit to a certain route.

[5150 Girl]

I told m,y SO the day we met,,, but then again, it was Holoween and I was Sarah Palin that year.

[BRANDYJ]

BrandyJ,
We have seen each other several times thoughout the week. So we have been on about a dozen or so dates. I agree that I don't think I want to let her in on this without knowing that she is someone that I would want to be with long term. I am looking for long term, but I have to know that she is one for a possible long term. I agree that it probably is still too early to figure that out.

I like the idea of putting out the feelers and seeing how she responds to some hypothetical situations. Like.,.. Did you ever consider dating (her bi friend). Or would you? I think those could be some good indicators prior to having a heart to heart about my femm secret. I really haven't given her many hints that there is a femm side to me yet. I don't shave my legs in the summer, and I haven't pierced my ears yet (would love to someday). So... I'll keep my feelers out for a little while more.

I also have to agree that I don't want to wait too long. I don't think a couple of months (4-6 months) would be too long.

GREAT ADVICE! I love all of the advice you can get in this forum. I would truly be lost without all of you!

Rob, you said that you think she is someone you want a long term relationship with. So at this point you are not even sure. But do you know if she is also thinking of you for a long term relationship? It takes two. Nothing wrong with your not being sure and going slow in considering if she is or isn't the ONE and only. The same can be said as to going slow in telling her until you know she is the one and when you know her goal with you is to think of pursuing a long term relationship with you. It's all about chemistry and it takes a little time to he sure you both have the right mix of those love chemicals.
Perhaps let her bring it up again. But this time, if she does, by all means sit her down and tell her how you feel about crossdressing and how it plays a role in your life and who you are. Don't put a time frame on this. When to tell is more about knowing it's the right time based on several factors including that chemistry and knowing for sure you and her want to pursue a long term relationship....As in being in love or falling in love.
It's when you start talking about being exclusive for each other. Again, I wish you luck.

[celtic.blue.eyes]

For both your sake, the sooner the better. The more she gets hurt, the more she will vent to her friends. How much you want your CDing activities advertised will be in directly related to how much she will be hurt.

[UNDERDRESSER]

I told m,y SO the day we met,,, but then again, it was Holoween and I was Sarah Palin that year.I just lost all respect for you! :p

[ReineD]

People normally disclose more and more personal things about themselves as the relationship deepens and the bond between you grows. Are the two of you beginning to talk about the more personal stuff, i.e. your deeper feelings about life, your goals, your childhoods, your past loves, your past joys & hurts, your disappointments, the more vulnerable things about yourselves, etc?

How serious is this relationship? Do you talk to each other every day and is there a mutual agreement that you are not seeing anyone else? If you're at that point and there is chemistry between you, then you should tell her now.

If you're still in a casual sort of arrangement with more general types of conversation, then it's not yet time. No one can put a time limit on this. It's a question of how serious you feel about one another.

[Elizabeth]

I'm certain this topic has been covered in here before, but I can't seem to be able to find a thread that addresses this. There are plenty of "How To" threads, but I think the "when" is pretty important too.

I have been dating a girl for about a month now. I have done some internet research on the subject of when should I spill my feminine secret, but have not come up with very good sugesstions. I have seen in some posts that it would be best to tell her early on, and others have stated that its best to wait. I don't want to wait too long. I don't think it would be good to wait until we are engaged and suprise her with Amy. However, I don't want to tell her too soon and scare her off. I plan on having a heart to heart with her. I just need to time it right. I am fully prepared to accept the possibility that she may reject me, but its better than being divorced.

I am aware that every situation will be different, but I would love to hear the communities sugesstions here. How do you know when the time is right to tell her about this?

Rob,

There is no time certain day when one should come clean. However, every relationship reaches the "is this serious?" or it does not. That is the time to say something. If you are serious about the relationship, or your partner is, it's time. As far as the 95% listed above? I'd say that is going to be the numbers game. 95% want a "real man" and 5% are going to be cool with it. From my experience, there is absolutely no way to know who will be in which group. It defies any kind of logic or rationale.

Love always,
Elizabeth

[Amy R Lynn]

People normally disclose more and more personal things about themselves as the relationship deepens and the bond between you grows. Are the two of you beginning to talk about the more personal stuff, i.e. your deeper feelings about life, your goals, your childhoods, your past loves, your past joys & hurts, your disappointments, the more vulnerable things about yourselves, etc?

How serious is this relationship? Do you talk to each other every day and is there a mutual agreement that you are not seeing anyone else? If you're at that point and there is chemistry between you, then you should tell her now.

If you're still in a casual sort of arrangement with more general types of conversation, then it's not yet time. No one can put a time limit on this. It's a question of how serious you feel about one another.


We have started talking a little more about some personal stuff lately. But the relationship is still very early. I can't really say whether this is going to be a long term relationship as of yet. There does seems to be some chemistry that I haven't felt with any of my other dates. I like to think that it will be long term, but its still early. We still have a lot of getting to know each other I think. Our conversations are mostly general conversations, and haven't gotten into deep feelings. We have talked past child hoods, goals, and past loves. I think I'm going to wait a bit longer. I just don't feel that the timing is quite right yet.

As for worrying about her telling all of her friends that I'm a girlie boy, I'm not too worried. I don't know very many of her friends on a personal basis. They are her friends and don't really have much connection to anyone I know. So... if it blows up in my face, I'll live to fly again.