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Thread: I'm in need of some dating advice....

  1. #1
    NEVER go bare-legged! Kimberly A.'s Avatar
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    I'm in need of some dating advice....

    Hey y'all!
    Well, I may be in need of some dating advice..... First of all, I have said in the past that I am a straight man, but I'm looking for a girlfriend. I'm on a dating site called Plenty of Fish and I don't have any pics of Kimberly posted there, just my regular, male self. LOL

    Anyway, I haven't had much luck there as of yet but when I do have a woman who shows interest in dating me, how should I go about breaking it to her that I'm a CD'er? I would be VERY nervous to tell her, especially if I really like her, being in Mississippi and any man doing anything even remotely feminine in my neck of the woods isn't considered to be the best thing in the world..... So any advice would be much appreciated!
    I may be crazy, but I'm BURIED in your memory!

  2. #2
    Silver Member Micki_Finn's Avatar
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    In my experience and opinion, it’s best to be upfront about that in your dating profile. A lot of modern dating sites have in-depth gender options.

  3. #3
    Junior Member Larissa Cassandra's Avatar
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    I do agree with Micki that the upfront approach is probably best, but it could turn some women off in a knee jerk kind of reaction (especially in conservative areas where CD'ing is more taboo than elsewhere). But if you don't include it in your profile, and you start dating the woman who has shown an interest, you should know early on whether this is someone you want to pursue a more serious relationship with. If she knows you're a decent person, then she might be open to your crossdressing even though it might have caused her to reject you before even giving you a chance. Totally up to you. You might want to try putting it on your profile first. If you get any hits, you'll know right away that any woman who shows an interest has already accepted your crossdressing. Good luck!

  4. #4
    Administrator Di's Avatar
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    My opinion follow Mickis advice .
    Saves a lot of time and heartache .

    Best Wishes



    ADD …there are women that would see that as a plus
    Last edited by Di; 08-27-2021 at 11:21 PM. Reason: Add
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    Sherlyn,My beautiful sweet girl
    You forever and always will be my one and only true love . ❤️

  5. #5
    Life is more fun in heels Genifer Teal's Avatar
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    I've always felt there's no easy way to bring it up. It's best to be clear when you first meet or in this case on your profile. This way you're not wasting anyone's time.

  6. #6
    GG Dutchess's Avatar
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    Micki's advice is best ,put it in the profile .
    IG : Knightress Oxide

  7. #7
    Gold Member
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    Micki's correct; Do it up front, who knows, you just might find that special person.

  8. #8
    Super Moderator char GG's Avatar
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    I echo all of those who say to follow Micki's advice.

    If you are up front, you won't have to "break it to her" later. Why waste time with someone who you find out later is not on board with CDing?

    Best of luck on your search

  9. #9
    Senior Member Geena75's Avatar
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    Question: how open do you want to be about your cross dressing? Would putting it in your profile effectively "out" you to any number of persons, who would also know your male self and where you live? Just wondering?

  10. #10
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    In principle, you should be upfront in your profile.

    The problem is, mention it in your profile and you will probably never even get your foot in the door, it will drive the vast majority of women away. At least if you get to know them first, and then tell, you might stand a chance.

    Of course, you absolutely MUST tell before you get married, have children or mix your finances and assets, or you are setting yourself up for a potential nightmare. (A pre-nup is also a very good idea regardless.)

  11. #11
    Weirdest woman ever! docrobbysherry's Avatar
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    I disagree with most here, Kim. If u r in the closet and have no desire to dress in front of anyone? U can do what I do. Tell people only on a "need to know basis". I didn't mention Sherry to any of the girls when I was dating because I never developed a relationship with any of them!

    However, if u go out or plan to out as Kim? U may need to tell a woman if and wen you're serious about her!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  12. #12
    Member Kris Burton's Avatar
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    In my opinion, it's gotta be full disclosure right up front in my opinion...in your profile, upon first meeting, wherever. Anything else is deceptive, and a big time waster for all involved - you might be surprised at the good result if you are totally honest .
    Best,
    Kris

  13. #13
    Feminaut Julie MA's Avatar
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    Being too open could put yourself in danger. In our controlled forum here, we often push each other to come out and be open. But, you mention that may not be accepted where you live. Just be open, verbally, once you meet someone.
    Inside my heart is breaking
    My make-up may be flaking
    But my smile still stays on

    C'est la vie CD

  14. #14
    Silver Member giuseppina's Avatar
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    Thank you, Julie. I disagree with most of the above posters advising placing crossdressing in a profile anywhere. That is just asking for trouble with a Capital T, IMHO. That is the primary reason I don't post pictures online of any description for any reason.

    I've heard rumours that some dating sites have been known to delete non-heterosexual postings. In their eyes, that means anyone outside the gender binary in heterosexual relationships.
    Cheers
    Giuseppina

  15. #15
    Gold Member Crissy 107's Avatar
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    I agree with Vickie and Julie, no need to put yourself in a not so good position in the area you live. I feel letting her know after meeting may be a better idea
    Crissy

  16. #16
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    Have a few dates with the woman. If you think that you find her as some one you would like to have her in your life and she you. Don't broad cast to the world.

  17. #17
    Administrator Di's Avatar
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    Quote Originally Posted by lingerieLiz View Post
    Have a few dates with the woman. If you think that you find her as some one you would like to have her in your life and she you. Don't broad cast to the world.
    What I-wrote above in my comments ( earlier in your post) is exactly how I would want to know . If would see that in a profile I would think how intriguing.
    Just remember the telling her after you get to know each other will be necessary but stressful.Is there a way you can made a Kimberly profile without broadcasting to the world?

    If you do not feel comfortable doing that then I like Liz advice above .
    Last edited by Di; 08-27-2021 at 11:26 PM. Reason: Correction
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    Sherlyn,My beautiful sweet girl
    You forever and always will be my one and only true love . ❤️

  18. #18
    Aspiring Artist Kelly DeWinter's Avatar
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    I was up front with Jeannie, even showed her photos dressed. She admitted she did not know much about it. She when to the internet and found the good and the bad info web sites on TG people, but she could sift the info well. The first date was watching "Just like a Woman" She asked a bunch of questions and we have been together ever since. The great thing about ten years later is that most of the crappy info on the internet seems to be going away. I'd sum it up by saying.
    . Be an open book
    . Be specific about things as they pertain to you.
    . Give anyone time to form their opinion
    . Have your life in order. No one like to be on a slow motion train wreck
    . When it come to topics like dressing, going out and transition make sure you don't make up answers on the fly. "Know thy self"
    . Don't rush into a relationship, If you end up with someone who will expect you to change or you expect them to change to suit you it won't work.

    Oh , I also encouraged Jeannie to come here and see what I have posted, but that was my decision
    Kelly DeWinter
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  19. #19
    Aspiring Member ShelbyDawn's Avatar
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    Dating advice is tough - and usually worth exactly what you pay for it.

    I can share that I have had two experiences where cross dressing has come up with a lady I was dating;

    In the first instance, my ex actually had a friend of hers in North Carolina write my girlfriend a letter outing me. I came clean admitting everything and she and I dated for about another six months. I never dressed in front of her but she was accepting of my wearing panties.
    It was her family situation, her daughter got pregnant and moved in with her, and the distance between us, about 100 miles, that ended things. We still chat occasionally but the spark is gone.

    The second was a second date with a very nice lady I thought had potential. We were having drinks and she pointed out a CD/trans woman at the bar, made some very derogatory remarks commenting that if "IT" came into the restroom when she was there, she would call the police. There was no third date.

    Your mileage will vary but I'd suggest waiting until you have an idea of how serious you want things to be and then play it by ear, the question may answer itself.

    And as others have said, honesty is always the best policy.

    Good luck.
    I am Me and Me is OK!



    Shelby

  20. #20
    Senior Member mbmeen12's Avatar
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    The problem is, mention it in your profile and you will probably never even get your foot in the door, it will drive the vast majority of women away.
    Well said and I waited for the third/forth date.
    Escapism isn't necessarily bad, but is definitely unhealthy in the long term. While helpful in the short term, things will degrade over time. At some point, the escapee will have to face the issue. Things simply blowing over isn't really going to happen in many situations.

  21. #21
    Silver Member prene's Avatar
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    I wait until either one of us gets ... how would I say this "attached".
    Unfortunately all my gf's break up with me soon after I tell them.

    It is not always them that break up, a few times I have found we do not match with her.

  22. #22
    Member Gi Gondin's Avatar
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    I would not disclose CDing in my profile, that’s for sure. But as said many times in this forums, once you clear some steps in the relationship and feel that she is the one, tell her fast!

    My advice here goes in a different direction - it’s about what are you looking for in companionship?

    You should search for signs and tips regarding acceptance, tolerance, proximity with diversity.

    I knew my girlfriend for a couple years in a professional setting before anything romantic appeared. I knew her opinions and where she stood in a lot of matters. That fact assured me that I had better chances of having CDing accepted. Worked a lot better than I ever thought.
    Last edited by Gi Gondin; 08-28-2021 at 04:53 AM.

  23. #23
    Senior Member GretchenM's Avatar
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    The many stories told here of tension between the CD and wife are highly correlated with hiding that fact until after the relationship is established or even been married, like, forever. It is a major factor in considering moving forward with a relationship. Turn the table around and think about how you would feel if you were cisgender and she was a CD and/or trans but you don't find out for 30 years. It is no wonder wives get upset and sometimes feel like they have been through a bait and switch.

    Micki said it, the GG's agreed, many others did too, and I say it as well after being one of those who have been through the grinder with a shocked and angry wife. We eventually reconciled and things are fine now as she understands that when we were dating I was not even a little that way. It came later, but I still hid it and that is deception and a type of lie. Big mistake. Don't do that!!!

  24. #24
    Silver Member JenniferR771's Avatar
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    Good point, Geena. Maybe you do not want the whole world to know from your online profile.

    And make yourself attractive. Drive an expensive car.

    When you go on a date, pay for the movie tickets with a hundred dollar bill.

    Accidentally mention the big inheritance you will probably get in a few years.
    After the honeymoon you can be gradual--let her find the panties in the back corner of you underwear drawer.
    Gretchen is right; hiding it is deception. Don't wait too long.
    Last edited by JenniferR771; 08-28-2021 at 02:44 PM.

  25. #25
    Member Lori Ann Westlake's Avatar
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    I'm not in the dating pool and have never used online dating. However, I personally would not put CDing into a dating profile. You're trying to sell yourself here, so this is a matter of sales and marketing strategy.

    Admittedly there might be a small advantage to mentioning CDing up front in the profile, insofar as anyone who responds is presumably CD-tolerant and might possibly be intrigued by it. However, given so many women's (often uninformed) reservations about CDing, I think this would be massively outweighed by the number of women who would simply write you off without a trial, who might otherwise have liked you as a person, CDing and all.

    If you're fishing in a dating pool called "plenty of fish," you've got to HOOK your fish first before you can even take the first step of getting to know one another. And if you were selling a product or service instead of yourself, how would you go about it? I always think of a smart lady named Janet Elsea in my town who wrote a book originally called "The Four-Minute Sell," a title she later changed to "First Impression, Best Impression"--the title on my autographed copy. (I attended a lecture she gave a couple of decades ago; she was very impressive.) Anyway the point is that if you're trying to sell something to a potential buyer, you have to make a good FIRST impression! That's what lasts in anyone's mind. You wouldn't start off by telling them how expensive the product is compared with others, or about its drawbacks and limitations. They'd just walk on by. You'd give them the GOOD news first, about how great it is and all the wonderful things it can do for them. Then once they're "hooked," you can afford to be honest about the cost or admit any other disadvantages. If they're already "sold" on it, there's a good chance they'll buy anyway, despite the cost or other considerations.

    It's the same thing here. Get the lady interested in you first. Maybe you have a few dates, maybe only one, and it doesn't look like it's going anywhere. If not, you never needed to disclose anything about your CDing anyway. But if it seems to be getting serious, and there's some trust between you, well, that's the time to let her know about your CDing. She may still walk (or "swim") away back into the dating pool, but if she's "sold" on you by this time she may well take it in stride.

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