Long.....
Disclaimer: This is all what I've learned over the years, they are mostly just my opinions. You are free to disagree, however I would like to invite suggestions as to how we can improve our odds in finding crossdresser accepting women, as so far, we have almost nothing to go on. Despite those who insist that those women exist, there is no current way to find them. And so......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
Trouble is, those 'surprising good results' are extremely rare, as rare as winning the lottery. I'm happy for those who have 'won', but expecting that good result as a way to plan out your life is going to be a huge disappointment for the vast majority of crossdressers. It's the same as the people who sell their house to buy lottery tickets; the chances are actually still very slim, and it's not likely to pay off in the end.
But what option do we have?
Well, as over the past 23 years having a profile online on dating sites, getting near zero responses with profiles I had that mention crossdressing (generally only men, and prostitutes, dominatrixes offering their services) I still date as a straight man, and carefully investigate how the woman feels about gender bending men. Little things like randomly adding 'Wong Fu' to our movie watching, or tuning in to RuPaul's show while channel surfing, to see her reaction to it.
We do get numerous people here, suggesting that there are, indeed, some women who would welcome us into their lives; unfortunately, NONE of them can tell us how to find those women. After all, most women derive some of their social status from that of their male partner, and a crossdresser isn't exactly an admirable type that other women (her friends / co-workers / relatives) would see as a 'good catch', so it's essentially a secret that she can tell no one, and many women feel the need to discuss their conflicting feelings with her friends; holding it in, can feel suffocating to them. In contrast, she will likely be made fun of by those other women, so she's unlikely to want anyone to know that her SO is a crossdresser.
So where does that leave us?
Date as a straight man; after all, if you're looking for a woman, you're mostly straight anyway. Carefully, gradually find out how she feels about us. Remember, there are a whole lot of women who are willing to tolerate men who crossdress, as long as it's not THEIR SO. The 'not in my backyard' sentiment is very, very strong in this. I can't site the source, but back in the 1990's after my wife found out about me, and we were seeing a therapist and searching through as much information as we could find about crossdressing and gender bending, there was one interesting book I found, and it had the following information (though, that was over 20 years ago, but all signs show that those stats may still be very close to today's.
About 6% of all women felt that it's okay for a man to crossdress. About 3% would be okay with having a crossdresser in their life, such as a brother, friend, uncle or such, but not as a mate. And a little under 1.5% would consider dating a crossdresser. When I brought this up to the therapist (who specialized in crossdressers, TS, among other things), she said that of all the couples that she had seen, about half of the women who initially thought that they could accept their SO as a crossdresser, eventually changed their mind and ended the relationship, having realized that she couldn't go on with it. That leaves about 0.75% of women who MIGHT be able to tolerate a relationship with a crossdresser, NOT at all saying that she'd be happy with it. So our chances are very slim indeed. The fascinating thing was, each category was about half the previous one.
So, if you're going to go by random chance, you're going to have to date well over 100 women to even hope to find one that MIGHT be okay with your crossdressing. And then, of course, there's all the other compatibility problems, for while some here have found a crossdressing tolerating mate, sometimes she's so horrible even that isn't enough to make us want to stay with her. It works both ways. So far, I haven't met any women who could tolerate having a crossdresser as a mate. And that's in the oh, 50+ women that I've dated in the past 20 years. At this rate, I'll be 80 before I get to date 100 different women and gradually try to see if she's okay with a crossdresser, and that's likely too late for me. But at least, I will have some sort of social life.
The best advice I've gotten, was to befriend gay women, and get them to let you tag along to gay bars perhaps slightly 'en femme', to see if there are any straight women there, who just might be curious about dating someone feminine, but not quite ready yet to date a woman. Perhaps if you pick up signs that she's curious about YOU, you can smile and see if she smiles back. Then go introduce yourself and see where it leads. DO NOT treat it like any other pick up attempt, be friendly and let her take the lead in the questions.
How do you spot someone who's interested in you? Read Leil Lowndes, 'Undercover Sex Signals'. It goes into detail, WITH PICTURES, of how women behave when they see someone that they are interested in. And it's right on target, I've used that information to completely turn my social life around. Now, I can easily know if my advances are likely to be successful, rather than having spent all of my earlier life, 'barking up the wrong tree'. Us men virtually always go after ONLY the women we find the most attractive, forgetting that those 'most attractive' women are also most likely to already have a SO.... so we are almost always, barking up the wrong tree. Change the odds, and start interacting with women that are giving off lots of IOI's (Indicators Of Interest). It works.
And last, let's remember that no one tells the other person everything about themselves to the other person. Sure, I didn't tell my ex wife before we got married; I really thought that I had either outgrown crossdressing, or 'beaten it'. After all, at that point I hadn't crossdressed in 10 years. I didn't learn that it was just buried in my subconscious, until it was brought to the conscious level, several years after we got married; then, I simply figured that all the good things about me would surely out weigh the one, little thing, that I crossdressed. Nope; I hadn't understood that when we fall in love, we fall in love not with that person, but what we KNOW about that person, and fall in love with the image we create about what we know about who they are. When that image drastically changes, such as her seeing us as traditionally masculine men, into the image of a feminine guy in a dress, the attraction can easily be destroyed; and then, the romantic love can be destroyed after that, essentially killiing off any romantic desire she had left for us. At least, that's what happened to us, and our marriage didn't survive.
PS. Leil Lowndes book is currently out of print; Amazon offers it on kindle, you can find the book in used book stores (if you are lucky), or check out the online book sharing sites like z lib that sometimes have it available to loan out.
Edit 2: Okay, I found the ebook on the same public book sharing site that I saw it on a few years ago, so apparently there's not been any copyright complaints about it being there. https://book4you.org/book/3631585/cbe630
Perhaps because the pictures aren't real clear, or, as Ms Lowndes stated, she really does want to spread the word about how men can better understand when a woman is interested in them. Either way, the book is worth a read, but if you do find it informative, please buy one of her other books, to help support her. The books she has written have been great information in helping male female communication.
Good luck. You're going to need a lot of it.
