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Thread: When should I tell my girlfriend....

  1. #26
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    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.

  2. #27
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    Quote Originally Posted by Ayame View Post
    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.
    Julie

  3. #28
    Silver Member DebbieL's Avatar
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    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.
    Last edited by DebbieL; 07-14-2012 at 12:17 AM.

  4. #29
    Aspiring Member Amy R Lynn's Avatar
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    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.
    "Oh my God, I realized, it's not that we're screwed up; it's just that we've been trained to thnk so."
    ~Rick Novic, Alice in Genderland

  5. #30
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    Quote Originally Posted by DebbieL View Post
    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.

  6. #31
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    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.

  7. #32
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    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.

  8. #33
    Silver Member BRANDYJ's Avatar
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    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.

  9. #34
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    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.

  10. #35
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    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.
    Last edited by jillleanne; 07-14-2012 at 09:26 AM.

  11. #36
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    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.

  12. #37
    Senior Member Jacqueline Winona's Avatar
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    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.

  13. #38
    Aspiring Member Amy R Lynn's Avatar
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    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!
    "Oh my God, I realized, it's not that we're screwed up; it's just that we've been trained to thnk so."
    ~Rick Novic, Alice in Genderland

  14. #39
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    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.

  15. #40
    Senior Member 5150 Girl's Avatar
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    I told m,y SO the day we met,,, but then again, it was Holoween and I was Sarah Palin that year.

  16. #41
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    Quote Originally Posted by Rob1329 View Post
    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.

  17. #42
    Lipstick Lez at heart! celtic.blue.eyes's Avatar
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    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.
    God's finest work of art is that of a beautiful woman.

  18. #43
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    Quote Originally Posted by 5150 Girl View Post
    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!

  19. #44
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    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.
    Reine

  20. #45
    TS Living full time Elizabeth's Avatar
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    Quote Originally Posted by Rob1329 View Post
    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
    [SIZE=3]It is always our choice, who we are-Waking Life[/SIZE]

  21. #46
    Aspiring Member Amy R Lynn's Avatar
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    Quote Originally Posted by ReineD View Post
    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.
    "Oh my God, I realized, it's not that we're screwed up; it's just that we've been trained to thnk so."
    ~Rick Novic, Alice in Genderland

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