Dating advice

[Aubrey Skye]

So, I know a lot of us usually just start the dating process and even marry, before ever bringing up anything about our other side. I was wondering if anyone here has been straight forward with the person very early in the relationship? I feel bad about hiding things and I feel like it should be something they know pretty early. That may not be the best approach though. For those with success, how did you go about this predicament of telling the person you were dating? How did you bring it up?

[Lorileah]

When my GF was coming out to meet me from Cali I sent her photos BEFORE so she could change her mind if she wanted. She didn't and she actually liked the idea. We spent 15 years dating and went out together often

[UNDERDRESSER]

There have been many threads about this.

I told my SO before we actually started "dating" as such. Why?

1. I felt it was going to be serious, I didn't want to be dishonest out of the gate.
2. I was virtually certain she wouldn't out me, pretty certain that it wouldn't impact our friendship, somewhat confident that she would be OK with it.
3. Very knowledgeable, smart, and perceptive woman, didn't think I could keep it a secret.

As of now, I don't consider myself a CD, though I am by most definitions, I don't try to mimic a female body, but i wear female clothes that work for me. Mostly skirts, underwear and hosiery.

[Rachelakld]

For same reasons as the others.
Girls always find "hidden stuff" eventually, so when you figure this is the girl for you, then it's time to share yourself with her.
Much better now than once you have 3 kids, mortgage etc and she views the marriage as a lie.

For me, after I cooked a lovely meal for us, had a glass or two of wine, I moved the talk around to womens fashion and mentioned I enjoyed wearing womens clothes. She was a little stunned so I then invited her to have a look at my collection (which was at the time quite classy dresses & skirts and 1 wig). I asked her if she wanted to try any on, she said yes, had fun with the wig and after a few changes we realized we were both naked at the same time :)
We have been married about 5 years now and loving every minute

[MissTee]

If you can see yourself getting into a serious relationship with this person, then yes. Share early. Otherwise, until you know, it might be a waste of confidence.

[LelaK]

I told a woman on a dating site whom I was messaging for a while that I crossdress. She said now she knows my secret and she blew me off, but not because of dressing. So in my last message I said, I sometimes wear women's pants that are indistinguishable from men's. That way I felt like she didn't have anything over on me and I didn't mention that I also wear dresses etc.

[charlenesomeone]

The contrast in this thread is telling someone you know vs not knowing well.
Also the individual girl made their choice. That says it all. Advice is great but
the real choice is personal.
Char

[Kate Simmons]

I told her before we go any further, there is something you should know. She had never personally known anyone that CD'd and she said so what?:)

[Ressie]

Once the date becomes steady and more serious I always tell. There's always the risk that the GF will freak and tell all of her friends, but that could happen at any stage of the relationship. If you wait too long, you may never fess up.

Now days, I think it's a good idea to find out how a woman feels about CDing before admitting to it. Of course, I'm single at this point of my life, so take this advice with a grain of salt!

[flogo920]

My wife of 34 years knew about my having breasts at the gate, and within weeks of meeting I took her to the Queen Mary in LA to see the female impersonators. She commented how they look better than most women. I explained my bra and CD fetishes (right word ?) but as I explained that that was for her ears only.

One X-mas she bought me "Girlfriend,Men, Women and Drag". We have had discussions. With the increase in our job intensities (surgeon and RN) and with the arrival of kids, one after 8 years of infertility one after 2.6 years of paperwork, a lot of $$ and a trip to Siberia CD ing took a distant back seat to our attendant responsibilities- between job and kids our really dream love affair went on an autopilot, but lost its intensity,

Since there is nearly no time to breathe ( she's of to work, and with her evening class I will not see her again till 10- PM), CD ing has no longer been a topic of conversation, but I assume no interest on her part as she is also buried in activities she cannot delegate. It has become non-issue. I still partially dress in the solo privacy of my office when I have disagreeable paperwork to do, but that's all.

[Beverley Sims]

My reputation preceded me and most who dated already knew.

Those that didn't were sucked into the fun of it and there was never any disappointment.

[Cheryl Ann Owens]

It's been so long I can't remember but my wife and I have been together since 1987. Today I have every liberty possible with CD'ing or beyond. It started around our third date when we were getting serious about each other. I remember saying something like, "What do you think about _________?" "Because I like to occasionally wear panties and even a nightgown to bed."

I waited for the bomb to drop and it didn't. Instead we talked more and I took it very s-l-o-w-l-y to say more and wait for her acceptance. Eventually she began to surpirse me with things after shopping. But I did take everything slow to allow her to adapt. I also probably overcompensated by bringing other qualities to our relationship to have her feel very secure being with me.

Today it's all second nature for us.

Bottom line is absolute honesty upfront and don't try to hide anything that destroys trust. It'll be a do-or-die experience. There are always more partners who would be great with you if another rejects this side of you. My parachute opened quite well! LOL!

Cheryl

[bridget thronton]

I think it depends on how soon you understand and know yourself as well as how sure the relationship will move past casual outings together

[chrissy111]

I told my wife on our 2nd date. I always knew I would not stop so I thought it only fair to both of us.

[docrobbysherry]

Tell her: If u suspect you're trans, you'll want tell your dates ASAP.

Don't tell: If you're a closet CD. Wait until your relationship appears to be getting serious.

Somewhere in between those 2 or farther down the Yellow Brick road? It's your call----:brolleyes:

[latex-steph]

After my last relationship ended for unrelated reasons, I had basically decided I was going to stop the CD part of my life because other things were more important to me. Bored/Drunk/I dont know what one night, I made a profile on a dating site that no one I knew was on where I flat out stated that I was a straight CD'er. A few months went my and it got a hit and I've been with the girl since. I'm glad things worked out the way they did, because even with me trying to stop cd'ing, I know I would eventually end up sneaking into a gf's closet. Find a way to be open from the start or very close to it. If this is a part of you, you need to accept that and make decisions based on the assumption it's not going away.

I'd say treat it like any other sexual fetish(I know its not for a lot of people, but bear with me) timing wise. It's part of what makes you happy. Whenever you would normally tell her what your into would be when I would break the ice on the issue.

[atlflygirl]

I am still very hesitant to say I crossdress since I'm gay, and most gay men want a masculine guy to date. They're much more stuck on that than women, in my opinion. The risk, I believe, is that they'll think I'm a potential transsexual since we as gay men aren't that far off brain-wise. While that is fine in my book, it's incredibly competitive to attract handsome gay men, so my crossdressing once in a while is something I don't automatically share. My interest in leather, however, is VERY important to me and I just about require that a potential suitor is open to wearing gear, going to seedy bars and fetish play. Definitely limits my choices.

[Alice Torn]

I have told every woman i was interested in, the last several years, and each time, it turned them off, and was a deal breaker.

[Steph_CD_62]

When I started dating my current wife I knew I didn't want to hide anything from her, and for her to be surprised later. I met her online, and had several conversations over the phone after we realized we lived near each other. I had told her over the phone my love for lingerie, but nothing else. When we finally met I knew she was the one for me and I didn't want to hide who I was. I knew if we were meant to be together I had to tell her early in our budding relationship. I told her within a week of meeting her face to face. She was a little shocked, but didn't say a lot. I explained as best as I could about who I was and where I was going with my dressing. We didn't talk for a couple days after that, and I didn't pressure her either. When we talked again she had questions and I answered all of them. That was 13 years ago and we are still together. She supports me although I know she wishes I would quit dressing, but she also loves me for who I am and doesn't really expect me to change either.

[Vickie_CDTV]

Every woman I have been in a relationship with, or even there was a possibility of such, knew about me. I met Old Lady though a mutual trans friend, so she knew before she even talked to me... and that was great, while it lasted...

That might by why I am so lonely... but at least I am honest and upfront every time. Sadly, that doesn't keep me warm at night... alas.

[CherylFlint]

I put an ad in “LOVE AOL” and said that I was a CD, and the usual other stuff. I received a response from a girl the next town over and we met at a restaurant. We hit it off and she asked me to come over to her apartment that weekend and “dress” for her to see how she could handle it, which I did, and she had no problem.
About a year later we were married.
Matter of fact, she took complete charge immediately and would help me with my makeup and so forth.
We went to a wig store and she picked-out a number of different wigs, and then she asked the SA to put them on me so she could choose which one she liked the best. She bought me a wig that day. I’ve wondered what the SA thought.
When she wants me to dress she’ll just say, “Go get dressed”, and I’ll go into the 2nd bedroom and there she’ll have laid-out the outfit she wants me to wear, sometimes including the jewelry and, sometimes even the bra.
My wife doesn’t even own a slip: I have many. My wife doesn’t own anything “see through” while most of blouses, skirts and dresses are see-through or almost. My wife always wears pantyhose while I always wear ff seamed nylons.
I’m more girly than my wife is.
NEXT DAY ADDITION: The reason why my wife makes the effort for me to "pass" is that, and I asked her once, that she'd rather be with and be looking at a nicely dressed girl than a sloppy CD.
We're to the point that she'll say, "Get dressed" and she'll have laid-out slacks or jeans and a regular girl shirt and we'll walk the dog together.
It's possible to have a good life as a CD with a woman but you've got to be up front about it.
My ad was on AOL for two years before I hit the jackpot. Most of the hits were of the "I didn't know what a CD was" type of response. Or "I didn't read the part about 'crossdressing'". Lame, so true. Be, nevertheless, true.
Many women who've I've come in contact with on the internet have expressed, "I wish there were more men out there who liked to dress".
Keep searching, and if the one your dating freaks-out about it, don't worry. Keep looking, you'll hit the jackpot sometime, it just may not happen overnight.
We have no problem with how the relationship works.
When we go out it’s just like two girls together. In stores or restaurants she does all of the talking.
We’ve been married for over 10 years and it works just fine. She’s the boss and I like it.
So my advice? Tell her straight off. If she has a problem, that’s her fault, not yours. There are girls out there who like CD’s, and for proof, I married one.
Many a time my wife will instruct me to wear my wig, bra, garter belt and stockings to bed. Works for me.
Good luck.

[carahawkwind]

I told my wife about 3 months into dating, the relationship was getting serious enough that I felt I needed to get it out there before it went too far. I dated a lot of women before I married, but only told 3, usually at roughly the same point in the relationship.

[Cally]

I made the mistake of not telling my first wife until 12 years into our marriage and WOW, was that the wrong thing to do.
She felt trapped and resentful that she did not know all the facts at the time we were married and that colored the relationship for ever after.
We divorced about 10 painful and lonely years later.
From that point on I vowed to disclose as soon as I thought the relationship was serious and found to my surprise that the women I told were actually appreciative and supportive.None went screaming off into the distance.
It was so good to get the Genie out of the bottle early and be able to then see if the person I was dating was actually compatible on other levels. God knows I had a few disastrous relationships still, but at least I know they were not down to CD'ing.
Basically, keeping secrets is not a good basis for a strong and lasting relationship.
I persevered and have found a wonderful woman and we married earlier this year. She is completely supportive and I love her dearly.
So my advice is - "If things are looking serious when relationships are starting out, be honest and respectful. If it doesn't pan out, well it wasn't meant to be. It's not as though there is not someone else out there who will understand and love you as you are - but they need to know who you are before they commit."

[sometimes_miss]

I told a woman on a dating site whom I was messaging for a while that I crossdress. She said now she knows my secret and she blew me off, but not because of dressing.
See, that's also part of the problem. Lots of women might feel guilty about being politically incorrect about being uncomfortable with crossdressing, so they deny it's really the problem, and use some other reason for the split. At least, that's how it worked in my divorce. Turned out she could have dealt with almost anything else, but the crossdressing was the true reason. And this seems to be quite true; lots of women stay with men who lie to them, cheat on them, beat them, steal from them, etc., but they stay with the guy because they still have that attraction to him But screw up the sexual attraction, and all bets are off, because she'll always feel the urge and will just replace her desire for you, with the desire for another, more masculine male.
That said, I carefully mention transgender things and see how the woman responds. I have yet to find a woman who finds crossdressing an attractive trait in a man. So, good luck, Aubrey. You'll need it.

[Stephanie Julianna]

There is no easy way. You just have to preface the talk with, "I love you so much that I have to tell you about......" If it is really true love she will stay with you. That does not mean she will want to be a part of it. That's when some serious compromising will come and some soul searching on both your parts is needed.

[ericanjtgirl]

My exwife found out and we got divorced. My current fiancee broke things off after 3 years and finding out.

[Jordan-NH]

Me and my GO met up on Match, so of course initial communication was through email and IM. We were getting along grate. And I've hit a point in my life where I decided being single was better than living in the closet and not being able to be me. So we had an IM chat where I let her know before even going on the first date. 2 great years later answers how I feel about the subject.

[Ressie]

I guess we could look at this from the woman's perspective. What if after years into the relationship she let you in on a shocking secret? Some would be deal breakers with many of us, some could be tolerated, but not many would be "That's wonderful honey!"

[Witchaywoman]

I am a natural born female who is into Cross dressers and transexuals. I'm not obsessed with them, and not a complete fetishist. I just kind of dig them. People keep telling me that those two groups are not necessarily gay, and that a lot of them like women. Then, when I go looking for them on dating sites, most of them are looking for males. I think someone should start a website for American cross dressers and transexuals who want to date females. I hear people here saying that they dated lots of females before they found one who understands. There are females who do more than understand. We like it, for whatever reasons. When I was younger, I met a small hand full of guys from Midnight Movies who liked to wear dresses. They always had a girl friend and it wasn't me. I think it would be awesome to have a boyfriend who let me paint their nails and stuff.

[ericanjtgirl]

Ive ruined a marriage an an engagement . Have yet to meet someone who accepts it as an acceptable lifestyle

[atlflygirl]

Ive ruined a marriage an an engagement . Have yet to meet someone who accepts it as an acceptable lifestyle

I met one guy who didn't mind it. If you do find that special someone, being yourself in his or her presence is phenomenal.

[CostaRicaRachel]

I'm in the same situation right now. I am seeing a girl, we are not dating but we see each other
almost every morning for coffee, we BBQ together 2 or 3 times a week, we got out to
the bars together. Everyone thinks we are dating/romantically involved but we are not.

It would not be fair to her to get romantically involved without her knowing about
my gender dysphoria. And I don't want to tell her for fear of loosing her as a friend.

I don't know what to do either. She may be moving, so I may not have to decide.

What's a girl to do;)

[Lexi_83]

So, I know a lot of us usually just start the dating process and even marry, before ever bringing up anything about our other side. I was wondering if anyone here has been straight forward with the person very early in the relationship? Yes, learned from bitter experience.

My approach is to mention that I'd dressed up on Halloween, more than once, and then depending on their reaction I disclosed this part of my life more fully, or knew it wasn't going to work.

Only been a year or so since I had a date with someone I first met dressed, not usually the way it's been.

[Aaron Zwidling]

Hang in there Witchaywoman, I'm sure you'll find some straight and single CDers if you keep looking.

I was straight forward and told my then girlfriend after dating for a few months. Twenty years later we're married and still together, so the honest approach has certainly worked out for me.

[JayeLefaye]

I try to keep things simple. I became comfortable with this CDing thing a while ago, and decided that it was not going to be a secret from someone who I might meet and spend the rest of my life with, and there was not going to be any secret closet in my future. Life is too short. So I underdressed on every date and let the chips fall where they may. It was simple philosophy really...If a date goes far enough that the outer layer of clothing was coming off, then THAT is the point of no return and she deserved to know.

Four times, in those five years it got to that point, and my tap pants and camisoles never once stopped me from getting, ahem, well, you know:-) The fourth woman became my wife and we've been together five years now, and as far as I know, we've never had to lie to each other about anything, and that's a lovely kind of relationship to have.

Best to everyone still looking!!!

Jaye

[ShelbyDawn]

I recently went through a divorce and while my dressing was a major issue to my ex, it was not the cause of the divorce. I honestly did not understand what my attraction to women's clothes was until my ex confronted me about it.
My earliest memories of wearing women's clothes go back to age five or six, I didn't really put the pieces together until just a few years ago so it is only now an issue.
I am in the dating scene now and think about this very thing every time I meet someone new. Do I risk telling them? Do I risk NOT telling them? If I tell them when? What if this? What if that?
I believe that the larger risk is in not telling them up front.

And Witchaywoman, if you're ever in the Austin area, well, ...:)

[JayeLefaye]

Ok...I tried to be subtle...Now I'll be blunt regarding dating advice:

Tell her BEFORE you introduce her to your family.

Tell her BEFORE you ***k her.

I hope I'm not being obtuse here...

If you are in the "dating" stage....

Jaye

[LookingGlass]

I don't know that I will be dealing with the dating issue of it, but having recently split from my wife, I agree with the consensus that be upfront about it early is the best option. It took years to finally admit to it to mine, and that was actually after we had decided to stop the fighting by giving out on the fight. Her take on it was very surprising and made me regretful I didn't come clean sooner, especially after moving from my dream town I had just moved to (god ol' ATX) to be with her. Sigh...

[UNDERDRESSER]

A very simple statement JayeLefaye, and perhaps a little too, direct? But yeah, best not to have any confusion.

It is definitely better to have it all clear to all. Not everyone is a suitable position to do this, and how you get around the problem of it possibly getting back to work, family, friends? That's dependant on your situation.

[Paula_Femme]

I met my girlfriend, who's now a member here, on-line, and told her about my 'dressing in my very first email. :)

9 months later our relationship continues to deepen and grow, based on complete honesty and trust, knowing that we can tell each other anything, without fear of being judged or ridiculed.

[StephanieCLT]

For me, I would definitely tell a SO in a dating relationship sooner than later. Maybe not on a first date, but once you start to know each other and begin to engage in emotional intimacy. I wish I had. :)

[ReineD]

My SO told me at the beginning, but we had already developed feelings for one another. I think it's a mistake to tell someone you don't know and that you've just started dating. If you've just recently met her, wait awhile to see if how it goes first. I wouldn't wait one year, but it wouldn't be unreasonable to wait a few months or even six, if you're both unsure of where the relationship is going.

When CDers tell near-strangers right away, I wonder if telling them is a sort of test, and if the girl doesn't accept right away then she gets dropped?


People keep telling me that those two groups are not necessarily gay, and that a lot of them like women. Then, when I go looking for them on dating sites, most of them are looking for males.

Yes, it's odd, isn't it.

I think the online activity is a fun pastime, a fantasy for many CDers and Admirers alike (those who specifically seek CDers). I'm told that a lot of CDs and Admirers just don't show up when it's time to actually meet. I suspect that a majority of CDers who look for men online turn off their computers when they're done, and they go out with women in RL.

[Paula_Femme]

When CDers tell near-strangers right away, I wonder if telling them is a sort of test, and if the girl doesn't accept right away then she gets dropped?

Yes, it IS a "test," if you will, to see if the potential SO can accept, or is willing to consider, a long-term committed relationship - not FWB!!! - with a crossdresser.

As for your contention that if she's not accepting SHE gets "dropped," I can tell you from DECADES of personal experience that it's the other way 'round... I'm the one who's been "dropped," EVERY time! :sad:

Why risk getting emotionally involved, then having "the Talk" at some point in the future, only to have her run screaming for the hills?

We BOTH end up hurt... again, why risk that?

[ReineD]

Paula, had my SO told me before I had developed any feelings, I probably would have opted to not pursue the relationship. Not because I'm against CDers (I'm not), but because I knew absolutely nothing about it and I thought that CDers were gay. So I would not have seen any future development for our relationship. By the time he did tell me, my feelings had developed enough for me to be willing to learn. I think this is the way it goes for most women.

[Beverley Sims]

I told my date up front but they knew beforehand anyway.

[CherylFlint]

Tell her from the VERY start.
First date is the time to show her some pictures of yourself.
Me? I was on "LOVE AOL" and said that I was a CD and she contacted me.
We've been married for over 10 yers.
Don't do the stupid "waiting to see if it gets 'serious' BS". Tell her from the VERY FIRST NANO SECOND.
At least be honest about it and NONE OF THIS "I was going to tell you", or "I was waiting to see how much I liked you" nonesense.
If you have any respect for yourself and for the other person, tell her as in PRONTO.

[sometimes_miss]

I think someone should start a website for American cross dressers and transexuals who want to date females.
Capitalism says no such market exists. There is a website called date a crossdresser, and it's inhabited almost exclusively by men. And it's impossible to search for the few GG's there, because about 99% of the crossdressers checks off the box which identifies himself as a female, screwing up the search engine. I was a member; you can join, search, but you can't send a message to anyone unless you pay. Supposedly, a few GG's there messaged me, but when I returned their message, either they never responded or said that they never sent a message to me, just like on Match.com.
Most people would love a sure fire way to get rich. Well, if you really know all those women who would love to date and/or marry a crossdresser, wichaywoman, here's your opportunity. Start a dating service for all those women. We'll pay for it. There are millions of crossdressers out there dying to meet a woman who will accept us as we are, and by odds, there are at least many thousands of crossdressers who are gainfully employed, good looking, good dancers, nice people, and at least decent in bed.
I've made this suggestion many times over the years here, and not one person who has claimed to know lots of women interested in crossdressers has taken any steps to make themselves millionaires by simply filling a supposedly available market need.
Because it doesn't exist.

[ReineD]

About a website for CDs who want to date females: I don't think that most females set out specifically looking for CDs to date, like Admirers do. But I do think that a rather large percentage of women will understand that the CDing is an aspect of their SOs and they'll be willing to work with it, once they've developed feelings for the person. I think the best bet for CDers (who do still live male lives even though they crossdress), is to join regular websites and start dating women without revealing the information immediately. If sparks develop, then by all means tell them.

[GenieGirl]

Well since I've started dating openly as a girl vs a guy I've found lots of success. I never thought I'd have that much success from so many women. Your best bet from my experience is to date as your female self. Many bisexual and even lesbians have been interested but I have not made anything serious of any of it as it isn't feasible to date as a woman full time so..... If you are open and comfortable going out on dates as a girl then great it should make it easier. The only drawback is that most of those girls may prefer you as a woman all the time throughout your relationship or most of the time.