Crossdressing and Dating: Does it ever get easier?

[Chancey289]

This question has probably been asked already, but I thought I should finally make myself a thread. So, as the title suggest, are relationships just doomed to be complicated when you're a crossdresser?

I've come out as a crossdresser to certain friends, and close family members (I even played a D&D session dressed), so I've gotten a little bit more comfortable with this side of me. However, when it comes to dating I always feel like I'll just have to get lucky finding a person who would actually be comfortable with this. I use to date a girl who really enjoyed my crossdressing, and loved me regardless. Yet, things didn't work out between us as time went on, and she broke my heart. After a long time recovering from that, I'm pretty ready to get back in the dating game, but there's always this doubt in my mind of possibly not being accepted that stops me from even taking a leap in to relationships!

How do any of you feel about this? Do you think unfortunately it's always gonna be like this?

[Erica Marie]

For me that is exactly how I feel. But it is all about attitude and how willing you are to put yourself out there. I myself have very low self esteem so it is very difficult for me to meet women, then add in that I am tg. Sadly I have given up hope. You are alot younger than I am, I feel your generation is alot more accepting. My advice is dont give up. Be prepared to have your heart broken a few times, but in time you will find that special person.

[Vickie_CDTV]

As someone who has been at this for a long time... it really doesn't. GGs who truly accept (much less enjoy) dressing are very rare, and don't come around often.

It is good you are honest about it though, it is even worse if you don't tell in the long run (though I know it sure doesn't feel like that in the short run.)

[Launa]

Its not easy but you are doing the right thing by being honest. You will find that special person!

[Maria 60]

I guess there are pros and cons to everything, there are men with cheating problem and drug addictions and gamble and there wifes sometimes never know. It's a crap shoot, it could go bad or good, it's really hard because if seems like timing is everything. At the end of the day there's nothing to lose and all to gain, if the girl doesn't like it your back to square one, but if she excepts it, there's all to gain. Roll the dice and see where they land.

[kittie60]

It's great that your Chinatown and upfront about it. There. Is someone our there for everyone, the problem is finding them but you will. Good luck to you.

[MarciManseau]

It's sort of like the old joke where a guy in a bar goes around to every woman there and asks if she'll have sex with him, and he usually gets slapped or punched. When a buddy of his asks why he does it, he says 99 out of 100 women react that way, but it's all worth it when you find one that says yes

[Adriana Moretti]

hey Chancey..you look young, which is a good thing, and you have plenty of time , in my experience with dating ( women that is) in the past mine were doomed too once they found out my shoe collection was better LOL , so for a while I gave up on girls , I am also bi, so....i started dating guys, ( no im not telling you to go do that LOL ) ...as time went on, and I got out more and more, I starting meeting girls out as Adriana, and have gained a few really good friends that way, still havent found one id actually have a relationship with, but to me its just proof that there are girls out there that do accept this, and are willing to be friends ( and even more) with gals like us, like im sure people here will say to put that issue on the table right away to avoid the heartache later, i agree with that too, and say what better way to meet a girl than to have Chancey meet them first ? That may not be in your cards right now but its something to think about in your future.....I dont know where you are on the CD/TG scale and how often this is a part of you, but if its a big part, that is an option to think about...

[Jenny22]

It's great that your Chinatown and upfront about it. There. Is someone our there for everyone, the problem is finding them but you will. Good luck to you.

Hi, Kittie. Your "Chinatown" remark is a new one to me. What does it mean?

[Alice Torn]

I can relate, but, i am 61 , and i am tired of heartbreak, too. I have tried dating guys as Alice, but found the huge majority just want you know what right away, so i won't meet them. I did meet three guys over the years, and two went ok, and no sex, but one lived far away, the other i think wanted you know what, and i would not go that far. Women i have told, are usually repulsed by it, for religious and cultural, tradition reasons, consider it deviant. Some of us may never find that right GG, and that is OK. A lot of guys that don't crossdress are having a terrible time in the dating world, too, and have given up.

[Jenniferathome]

Chancey, did you somehow search for an accepting cross dressing girlfriend when you met your prior GF? No, you met a girl you liked. THAT is exactly how you will meet your next girlfriend and someday, your wife if you want that. All the things you want in a GF you will want in an "accepting of cross dressing" girlfriend.

Relax. Cross dressing can take a backseat when meeting new people. After you have found someone whom you think could be a serious relationship, sit down and tell her.

[AllieSF]

Actually, reading so many threads here about dating, marriage, tell or don't tell, told and broke up, told and DADT, told and, wow, acceptance, I am going to throw out here some heresy, for fun. So many here like to say that if you have a good relationship and you reveal all after getting married things will work out. So, why not keep the secret, marry the one you love, make that special effort to have that perfect relationship and then reveal your secret. I am guessing that you probably will have better luck that way than finding that extremely small needle in that extremely large haystack!

The truth is that those special women/girls, like the one that you found and eventually separated from, are rare. They are out there, but good luck in finding them. As Jennifer said, find one you like/love and then reveal when you think things are getting serious enough to risk telling her. The risk in revealing to a non-committed partner are real. Is a negative and/or damaging reaction probable? Probably not so much! But, unless one is ready for the unwanted consequences of an unpredictable woman scorned, you do need to try to make sure that you have a good idea of their potential reaction and ability to keep your secret if you need that secret kept. Keep looking and dating and maybe you will be lucky again with a keeper this time. If you find one with an older accepting sister or aunt let me know.

[RADER]

I lost my wife about 3 years ago. (Wow time goes by fast) I am 68-going to be 69 soon.
Not many out there that will accept cross dressing at this stage in life. My wife was a
great person, she accepted me, even helped me, but I promised her I would stay in the
house and not go out and embarrass her.
When I go out on a date I guess I try to see my date as I saw my wife. On one recent occasion
I brought up the subject of cross dressing from a news broadcast about Bruce Jenner.
WOW !!!! Did I ever step on some toes with that. This date was all over the subject on
the fact that any man would want to be like a woman should be committed somewhere.
I could not wait to get her home; and I do not return her calls.
So if you are younger than me, You just might have hope, As for myself, I will enjoy my dressing
at home, like now, sitting here with a nice LBD, And enjoying the day.
Rader

[TaraGrace]

hi Chancey,

Good question, and glad you asked!
you'll read a lot of yes and no response, great thing about the forum.. at least you'll get a fair share of advice from both sides.

A few thoughts come to mind.. read through some of the serious topics in here, generalising the two worst case scenario's being
-> honest about crossdressing, never finding a partner
-> not mentioning crossdressing, living decades in lies and fright of being unmasked

I'd know what I would pick, but it's all about what you want to pick.

Let's get honest, when you're young, as a guy dating girls, it can be tough enough for a lot of guys.
There's milion reasons you might want to see crossdressing as complicated and avoid it.
As are there milions of reasons you might get your heart broken.. such is life :S

And then, keeping in mind a lot of dating is done online these days and the world changes a great deal..
I'll do you a solid and share you a little secret:
The one thing you never want to be is the "hey what's your name", "you look hot" or "haven't I seen you before" guy.
Ladies get messages like that 20, 30 or more times a day.
I date a lot (men and women) and in general just standing out from the "you look hot" guy.

Do a quick google on "peacock theory", there's a lot of links on that topic, the summary is being different and standing out.
Standing out and being different.. hmm, see the bridge I'm trying to make to crossdressing?

Sure.. it might limit the playing field a bit.. but won't it also leave over players in the game that fit you better?

For me, happy and in love.. but if I had to go out and find a new soul mate, I'd rather find someone weird like me, then settle for vanilla.

x Tara

[suchacutie]

The short answer is that all relationships are complicated. The good news is that personal lifestyles are being seen as ever less of an issue. The younger you are the easier it will be. I didn't say easy, just easier.
The best thing you can do is to exude confidence and simply expect that being gender fluid will not be an issue. Don't apologize, and don't see it as complicated. If your potential mate wants it to be negative or complicated, just move on. Be yourself and a potential mate won't need confused and you will find someone very happy to get to know you well.

[sometimes_miss]

In the sixties and seventies, we were told, 'the times, they are a-changin''. We were told that society was changing. And, that people were changing. I had just started asking girls out, and of course, none were interested, I remained in the friend zone for many years. Yet, the women I spoke to, always assured me that SOMEONE ELSE would be interested, that there was someone out there for everyone, and I should 'just be myself', and I'd find the girl for me. It was always going to be SOMEONE ELSE. Not her.
Needless to say, 'being myself', that never worked. At some point, I realized that women were attracted to a particular type of guy, and I wasn't that type. So, I had to change. And, change I did. and all of a sudden, I started getting dates. So much for 'someone out there for everyone'. If I'd never changed my style, I never would have gotten a date at all.
Women are generally attracted to certain types of men. Tall, in shape, has a good job, has a nice car, we all know the stereotypes. Yet, we are told 'there's someone for everyone'. Which is not true. There are simply not enough women interested in crossdressers to go around. If there were, someone would have started a business and be making money at it. Let's face it; there are dating sites for all kinds of couples. But 'single straight girls' and 'crossdressers' sites don't exist, and we all know the reason for that.

So the answer to the OP's question is, NO, it never gets easier. And as long as women are attracted to the same type of man, it never will. Because I don't see any change in that attraction in the past 40 years. Something in it appears to be genetic, femininity in a male appears to be a sexual turn off for nearly all women, and has stayed that way even though women's options have expanded greatly. And that means evolution is involved. Evolution works very, very slowly, if at all, as there has to be a significant advantage in survivability for a genetic mutation to become widespread. And marrying a crossdresser doesn't appear to offer any such advantage. So basically, we're out of luck.
Let the flames begin.

[raeleen]

I think it can be tough, but depending on where you fall in the spectrum, it really changes. Are you someone who needs to dress all the time? just once in a while? do you like going out with friends often in girl mode? just enjoy dressing at home? all of these things will shift how a potential partner might react. Assuming of course that they're reasonably ok with it to start with. I've always believed that being honest is important, and if you tell and she isn't into it, but is willing to talk or figure out how it fits in your lives together, then it can work. it's not so different than any other aspect of a relationship where compromise or dialogue and communication are needed.

something i think is important to consider too is that your dressing really shifts how a woman can feel about their own identity. dating someone who is a crossdresser or trans really does impact how one is viewed in a relationship (and i mean from both sides).

good luck, chancey. you'll find someone out there. I know it.

[ReineD]

Chancey, just try to go out there and meet girls without thinking too much about whether she will be into the CDing or not. Just find someone with whom you have stuff in common, someone you enjoy being with just as much as she enjoys being with you. Try to not have an agenda.

And then after sparks develop, you can share more deeply about yourself. Chances are she'll be OK with it if she has fallen in love with you. If, on the other hand, you think you may want to transition then this is a different matter. Most hetero women are not wired to want to be in relationships with other women.

You may not find a long-term mate right away, but few people do. It usually takes some years of trial and error and I dare say that a lot of people date all through their 20s before finding that special person with whom everything clicks.

Women are generally attracted to certain types of men. Tall, in shape, has a good job, has a nice car, we all know the stereotypes. Yet, we are told 'there's someone for everyone'. Which is not true.

I disagree!

Look at all the couples around you. Some are attractive, others not so much. People are tall, short, thin, heavy, athletic, nerdy, etc, with varying levels of socioeconomic achievement. And they find each other! It's true that people tend to choose mates of equal level of attractiveness to themselves, but there is someone for a heavier, awkward looking young woman just as there is for the cheerleader. Same holds true for guys. For most people the attraction is to the person inside and how much two people have in common more than the outward appearance and how rich they are.

Have a look at these random yearbook pictures, one from the '60s and one more recent. All types of people there. The guys are not all tall and handsome and I'm sure they didn't all get good jobs with nice cars, and the girls aren't all knockouts, but they likely still found someone to mate with:

http://sheboyganhistory.com/images/1966/sshs1966-64.jpg
http://www.parkdalealumni.com/Images/77parkdale197f.jpg

[Curiosity666]

I've recently come out of a 4 year relationship with the main cause for separation being, you guessed it, crossdressing.

Do I worry that I will never be able to find a partner that accepts the whole me? You betchya.

Are there other men out there that have certain kinks (not that this is a "kink"), that worry they'll never be able to find a compatible partner? Damn right.

Am I going to keep trying and be upfront about things? Hells yeah

[Alice Torn]

Sometimes Miss. The only place i disagree with you, is that women want a tall man. Many may, but in my experience, as a very tall man, the girls , like Reine said, go for the man inside, mostly. I have been rejected by many women, who chose shorter men, and many tall women who married shorter men. Now, with a divorce rate around 50%, women and men often still choose a wrong person. I know i would have been in disaster, had i married some of the ladies i wanted to marry. Good thing they rejected marrying me!! Lifetime single here.

[UNDERDRESSER]

I'm kinda thinking the same as TaraGrace, you say some of your friends know about your dressing? How about going out somewhere as a small group, maybe an obvious mix of singles and couples, maybe just as a group of obviously platonic friends. Which one would work better? Depends on where and who. See who you can get chatting to. (You dressed of course) The only problem might be if you really can pass from close up, they might miss the possibility. I wouldn't try and ask for a date if they haven't realised you're male, they might freak out or completely misunderstand. One thing is for certain, there won't be any surprises later, or any complaints about deceiving them. Pretty fast way of sorting out the ones who aren't accepting.