Divorced and no idea how to date as a crossdresser

[kaylyn]

I recently got divorced and am finally ready to go out but I don't want to start with a lie I want whoever I date to know. So how do you date girls in this modern day and age as a crossdresser?

[cdinmd206]

Good luck on finding that girl. At 64 years of age and 25 years of marriage, I am finding it very difficult to jump back into the dating game.

[Mollyanne]

That's a tough one!!!! Just dating slowly at first, then when you have been seeing the same woman for a while kinda' feel her opinions and see where it goes. Good Luck no matter what.

Molly

[phylis anne]

well not to beat an old horse but there are legitimate dating sites (not the porno ones) that have you fill out a profile of who you are and what you are seeking this gives people a chance to see where you are at and if they like what they see maybe possibly a relationship will develop.
hugs phylis anne

[marlacd]

First, I'd find an a lady that showed some interest in you. Once you're done that, then toss out some generic comment. Like, "I saw a crossdresser out at wallyworld today, and he had 5 o'clock shadow." Then, listen for a reply. If it's nasty, then you can assume that she isn't going to put up with your dressing.

Right now, with the transgender argument going on, or Caitlyn Jenner subject being a topic of conversation, it's easy to test the waters. If you're lucky enough to get some sort of positive reaction, then I'd go deeper and more personal. i wouldn't say anything within a small group of people about that. She just might agree with the group consensus only to fit in with them.

Be prepared to be shot down, A LOT.

[heatherdress]

If you want to immediatele identify yourself as a crossdresser to start dating, get used to being alone. Try to be realistic. What type of message are you sending out to any prospective woman you meet if you immediately tell her about your cross dressing? It would be that your weird hobby or behavior is so important that you make it a priority to deal with immediately. The message is not only that you do something hard to understand and accept, it is also more important than anything else - even more important than her. If you really want to date and successfully meet women who could accept your crossdressing, you probably should not tell her you crossdresser until you know each other. Or else you will be on this site complaining about being alone.

[Mykaa]

Well kaylyn I am in a similar situation, I have wondered about this many times. I have been on dateacrossdresser, I found it to be dead and the only active people to be other crossdressers, I started a facebook account just to try to talk to a gal I found there, she never answered. I know the only thought Ive had to that is put myself out with other people similar to me and hope I meet someone that way. I see a lot of good advice here allready, but it seems like the best way is just finding someone then getting to know her and hope for the best....

[Amy Lynn3]

Try Plenty Of Fish.com. I ask anyone I am interested in if they would like to chat and find out more about one another. After the talking starts easy the conversation to things one likes outside the vanilla world. Talk about that for awhile, then say you would/have wanted to dress as a woman. You will get different results, but some have told me yes. The relationships have ended for other reasons.

[Piora]

Good luck on finding that girl. At 64 years of age and 25 years of marriage, I am finding it very difficult to jump back into the dating game.

Yes, indeed. I am in the same boat, and have been on dating sites since I divorced 10 years ago. I am also 64 and have tried a number of different sites. I get almost NO replies to those I message. I have been told by other people that I have a great written profile, but I think if I put down that I crossdressed, then I wouldn't get any replies. At all. Ever.

Well kaylyn I am in a similar situation, I have wondered about this many times. I have been on dateacrossdresser, I found it to be dead and the only active people to be other crossdressers, I started a facebook account just to try to talk to a gal I found there, she never answered. I know the only thought Ive had to that is put myself out with other people similar to me and hope I meet someone that way. I see a lot of good advice here allready, but it seems like the best way is just finding someone then getting to know her and hope for the best....

I think that if I ever DID meet someone and she was "the one". I would be terrified of losing her by divulging that I crossdressed. Of course, over time, that might change. I would have to test the waters, as has been suggested by others here, but I could see myself living that part of my life still closeted, and take my secret to the grave. But, I guess I would cross that bridge if I (ever) come to it.

Let's see: Find a woman who is tall, great sense of humour, that I'm attracted to, doesn't smoke, honest, trustworthy, compassionate, understanding......and has no issues with me being a crossdresser. EASY!!! Right?

Try Plenty Of Fish.com. I ask anyone I am interested in if they would like to chat and find out more about one another. After the talking starts easy the conversation to things one likes outside the vanilla world. Talk about that for awhile, then say you would/have wanted to dress as a woman. You will get different results, but some have told me yes. The relationships have ended for other reasons.

I'm on PlentyOfFish too. My issue is that on the rare occasion that I would meet someone with whom I was compatible, the chances that she wouldn't head for the hills after finding out I crossdressed, are slim to none. It's very difficult to meet someone at my age (at least in the area where I live) In the last year, I have managed to interest ONE woman to even simply meet for coffee, through one of the dating sites I use. Didn't work out.

[nikkiwindsor]

Recently, someone (cannot remember who) posted the below youtube link...it's a wonderful documentary about some crossdresser/SO relationships in the U.K. I think it may give you some ideas about finding a new relationship! I have the greatest hope & optimism that you'll find that special someone who will accept you for who you are! True relationships are founded on trust & unconditional love. In this whole wide world, you only need one, just one SO. That person is out there waiting for you and just doesn't know it. Your lives simply need to intersect! Nikki

https://www.youtube.com/watch?v=zV6bStI7St8

[JenniferMBlack]

I wish I could offer some great insight here, having been there a couple of years ago. But it was just luck for me. I was friends with my girlfriend for a year and a half before we started dateing. She was dateing a friend I had to cut loose because he was a horrible friend. She broke up with him around the same time and we went out as friends a few times. Then as things do it just progressed from there. Bonus she already knew I was a cross dresser before all of us so no supreme and no lies.

[Alice Torn]

I can relate, but i am lifetime single, 62, six foot six, odd religion, too. So, I have tried dating sites, dateacrossdresser.com, adult friendfinder.com. Ts date.com. but only get rplies from guys or CDs who want sex. Tried plentyoffish.com, when it was free, mention my cd in my profile, got zero hits. Now it is not for free, and i am low income, and can't afford to be paying on dead end sites. The few women i knew before i got back into dressing, think it is wrong, and i must quit it. I hate to say it, but some of us, may never find a GG who will accept, especially us who are senior citizens. Young one may have some success, but us older ones, it may be a snowy day in August before we do. Older women are mostly turned off.

[Piora]

Very true, Alice. Older women were raised in the 50s and 60s and I think they view that, for the most part, as a 'perversion' or a 'something weird'. Not all, but many. Younger women seem to be more open, and less hung up on things such as someone (anyone) being gay, transgendered or into crossdressing.

[char GG]

I know that dating sites are popular, however, there is no chance for women to get to know you unless they meet you. The CDers that I know that have met someone put themselves out there. You may meet someone while in girl mode. A few CDers that i know have met someone while in man mode and got to know each other before the big reveal.

One of the girlfriends was ready to stay on board with the CD guy until he totally blew it one night while dirty dancing in girl mode with another man. I could see it written all over girlfriend's face, I had to extract her from the ladies room before she would talk to the CD boyfriend. Girlfriend was still going to stay with CDer but he blew it again because he was such a selfish "b", and she ended up bailing.

There is another CD that I know who met (in person) the "woman of his dreams" and thinks he is going to quit CDing for her. (We will see how that goes).

I also think you have to know your level of CD/TG/whatever, before you are able to explain it to a new lady who doesn't know anything about it. Just my opinion, but you may also have to make sure you do things with the new lady while in man mode and not complain about it. Women usually want to be the woman in the relationship, not a new girlfriend. If applicable, make sure she knows that CDing is not the most important thing in your life. Hopefully you have other common interests.

[sherri]

I recently got divorced and am finally ready to go out but I don't want to start with a lie I want whoever I date to know. So how do you date girls in this modern day and age as a crossdresser?

Short answer: you probably won't. Still, I would suggest that you can best explore that most slender of chances by skipping the online approach and getting heavily involved in some sort of regular face-to-face social interaction.

[~Joanne~]

forget the online dating, complete waste of time. I know we are in the age of technology but somethings are best done the old fashion way. I wouldn't want to bother with someone that uses the internet for dating, it's a clear cut sign to me that she is lazy.

[Amy Lynn3]

Good advise by Char GG. To Piora and others who don't have very good luck on dating sights. My advise is... have your pictures updated. Show an assortment of pictures. Some in a coat and tie, others in casual, with some doing fun things. My best advise is have one photo with you posed with a look of confidence all over. One other thing.... be sure to smile and have pictures showing your face. Be sure to be honest on your profile and don't over sell yourself.

Don't think just because you are old it is the problem, it is not. I am 70 years old and I never need to ask anyone for a date. They contact me and I pick who I date. I followed my advise. See if it will help you to.

PS: I do not want to be married again, as I just look for dates. Some is a one time meeting and one lasted a year. I told two of the women about Amy, with mixed response.

[Piora]

forget the online dating, complete waste of time. I know we are in the age of technology but somethings are best done the old fashion way. I wouldn't want to bother with someone that uses the internet for dating, it's a clear cut sign to me that she is lazy.

VERY strongly disagree, Joanne. There's a thousand reasons why people use dating sites and I doubt that laziness ranks even 5% of why they're there. For example, some men and women live in small communities, don't have a vast circle of friends and relatives that MIGHT know someone suitable, and they want to expand the pool of possible connections. Many people are choosy - not lazy. The good thing about internet dating sites is that you can "window shop" to narrow things down, and already know a lot about a potential mate to judge if they're suitable. The ability to weed out men and women that you have nothing in common with is invaluable.

[~Joanne~]

The ability to weed out men and women that you have nothing in common with is invaluable.

I am not saying your wrong but this could also be done face to face and spending some time with each other. while it may seem like a "good idea" how many people online are also lying about who they are, what they do or even as simple as to what they even look like? Online makes it too easy to be whoever you want to be, if the only reason to date online is to tell someone that you CD, it seems the wrong reason to me.

[Tonya Rose]

Internet dating is BS. If you want to find like minded people they are right there in your community.... not the other side of the world.....think about it... how many lie`s are you telling between here and your reality???

[Piora]

Well, Joanne, all internet dating actually is, is a tool. It's simply one additional step..... another way to meet someone, that you wouldn't otherwise have been able to be in contact with. Over the years, I've met a fair number of women (although not recently ). They all looked exactly the way they showed themselves in their profiles. Now, I'm not saying that you'd be wrong if a few of them might not have been honest about some of the things you mention, such as what they do for a living, or if they're not single. I never got to find out with most of them. But that's true of anyone that you might meet - anywhere. Just because you met them through a dating site doesn't automatically make them serial killers. Or liars, necessarily. Or that they have something to hide. I don't see any point in someone pretending that they are 6' tall when they're barely 5' 2", or that they weigh 110 pounds when they weigh 300 pounds, considering that the ultimate goal is to meet. Pretty hard to explain away lies like that. That has never happened to me in 10 years, but I have heard it from women that I have met, about how it did happen to them. Seems a fair percentage of those who deceive are men.

if the only reason to date online is to tell someone that you CD, it seems the wrong reason to me.

Well, that's for sure, and I agree. However, while I have never seen a woman's profile that mentioned that they crossdressed, I have seen women who mention that they are transgendered in their profiles. There was no mention of whether post or pre-op, but that's irrelevant.

I think dating sites get a bad rap these days. Bad dates and bad connections were happening long before the internet.