Tips for younger single guys trying to meet someone accepting to date?

I'm 31 and trying to come to terms with CDing, which has been a theme throughout my life, but has only become something substantial in my life (ie, a semi-regular thing) in last 8 years or so. I've always hid it from my girlfriends and I hate that it's been that way. Even the two that I truly loved, I felt like I could never tell them and that the attraction would end immediately (not to mention their ability to keep it a secret...loose lips sink ships as we all know). And that deception with someone you love and care about doesn't feel good at all.

So trying to adjust my approach and meet people from the outset that would be accepting (and maybe even embracing?) of this quirky need that I have, but to be honest I have no idea where to start. And to be honest, since I moved out here (Boulder CO area) a couple years ago, I've found it generally very difficult to meet girls (as a "normal" guy), much moreso than back east, and so adding in this very specific additional criteria makes it seem like either I need to just take what I can get, or somehow adjust my approach.

There's a lot of collective knowledge and experience here -- what have you guys/gals, who have successfully navigated the dating scene as a CD, done that has helped you in finding an accepting "soulmate"? Any lessons learned? What would you do differently if you had the opportunity? Any particularly useful sites/resources?

My hope is that we can cobble together a list of tips might help anyone in a similar position to me who comes across this thread, but in case it helps with giving me some specific suggestions, here's a bit more about me and what I'm looking for.
- I've only dated GGs so far, but am open and curious about being with other that are anywhere on the gender spectrum (guys, girls, or anywhere in between - CDs, TSs, etc)
- Looking for someone in roughly my age range (mid 20s to mid 30s)
- Looking for dating. I'm not really a fan of one night stands. Having a one time thing with a guy (or TG) would be exciting, but I'm also concerned about staying safe and not contracting/spreading disease, and it seems like the slower approach is better in that regard.
- I'm looking for a real connection, but without expectations (eg, perusing the craigslist miscellaneous romance m4t section, you see a bunch of guys saying they're looking for a good sissy to be their wife...not 4 me)

I'm 24, found it easier to just just tell them. One girl asked why and I told her and basically it was just like whatever. Told another one I just talk to and same it's just like whatever. We're both young so I believe our generation is more understanding.

It is similar and difficult for us old timer singles, too. I am 62, never married. Last week, i did tell a postal counter lady, and showed her some pictures, and also showed a very young lady who worked at the cleaners, where i get dresses altered. I am much less likely to tell or show men, but did buy some stamps from two male postal workers in Wisconsin last year. Fully dressed.

That's awesome Justina, thanks for sharing! At what point in getting each other did you tell them?

Its best to just come out with it when they ask what kind of hobbies do you have? or what do you do on the weekends?
If you just admit you dress and act like its no big deal they will get the idea quickly.
They may ask a lot of questions so be ready to answer them honestly.
I have done this several times with dates and they either find it interesting or revolting so you have a 50/50 chance.
If they can't deal with it they will tell you.
Its not like you would want to date a person if they couldn't deal with you CDing right?
I'm gay and some guys I have gone on dates with are cool with it and some aren't same goes for women.
I did date one woman and she was very interested and thought the idea of a man that was strong enough in his sexuality to dress like a woman and not be scared of what others thought to be very sexy.

I always told my GFs, from the point of view of a guy who was interested in them and attracted to them, and generally it was accepted [in those days, wearing panties and a babydoll nightgown] since it is kind of understood for what it was, a way to participate in the sensualness of lace and nylon. Some girls were totally relaxed, since they saw women's clothing as costume anyway. Some were a bit annoyed, but it didn't change much about lovemaking, and gave them a few minutes of an interesting experience. I think the difficult times for women are when it becomes either public or more like trying to be a woman. Both of those undermined their safety and identity.

You mention wishing for safe sexual encounters with men or TG, and so you may give off confused signals at a deeper level to girls - so that they feel your interest in crossdressing includes roleplaying fantasy, rather than just a kind of gender sensitivity, and so you are not fully present with them or committed for the long term.

Bottom line is that most people are looking for sincere relationship, and sexuality is just part of it and not the most important part of it, so if they feel you and they are really connecting as people, a lot of things can be incorporated in about each other as you form the partnership. Being completely honest is critical, as it comes from trust and trustworthiness, and your partner has to feel and more central and important to you than your next new dress.

Just threw it in there when they asked me about all my piercings and why I had eye liner on.

I don't think it's wise to try and date with the intention of dating someone you know will be accepting of crossdressing from the get go.

It's part of your personality, and you should just date regularly until you find someone who is accepting.

As for a date "spilling the beans" on you, I wouldn't worry. I doubt anyone is that petty. Even if they are, who would they tell? Chances are they don't know anyone in your life. Even if they did, who would your friends and family believe? You, or the crazy ex?

I told my wife on our 5th date, when things were starting to get serious and I wanted her to know me properly before we got in deeper.

Emily, your whole approach to dating seems extremely thoughtful, intelligent and open minded. But I think you're just as likely to find an accepting partner by random dating as you are by seeking certain criteria- life is weird like that. I'd be asking out the cute girl/guy who works in the whole food store rather than trying Craigslist.

What you're really looking for is unconditional love, and that's the holy grail for everybody. Having said that, you certainly stand a better chance in CO than you would in Utah.

My own opinion is that you should be honest from the outset, because crossdressing is controversial, and if you want an honest partner you can't very well be less than honest yourself. If you're honest, you're taking responsibility for yourself - and that's a huge, brave thing to be and do. But it's really all you can do, in terms of laying the foundation for a solid long term relationship- beyond that it's down to chemistry and the other person's mental/emotional abilities.

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Originally Posted by Justina

...it's just like whatever. We're both young so I believe our generation is more understanding.

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Hmmm. Shrugging and saying 'whatever' may indicate genuine open-mindedness, but it might also indicate shallowness and a lack of self knowledge that will only be exposed further down the line, perhaps when the subject of having children comes up. My feeling is that although transgenderism is becoming more widely accepted, human nature changes very little, and most women choose the nearest thing to an alpha male they can find when it comes to finding a father for their children.

So let us know how it goes Emily, I think anybody would be very lucky to have you.

As the general population of women isn't amenable to dating crossdressers, perhaps the best advice is that which someone else gave here a while ago. Cultivate friendships with gay women, and get them to bring you along to bars which cater to them. There you might find a woman who's more likely to be curious about her own sexuality and perhaps her attraction to the feminine, but maybe not ready to actually date another female. Of course you'll still have to be able to recognize if she's interested in YOU, but that's another topic.

I agree o

I'm 32 and newly single (yes, it was a factor). From now on, I will make sure to either lead with it, or make it known very early on in the talking stage. It ties in neatly enough with my awareness regarding feminism, gender (in)equality, and so forth. There's no reason to hide anymore, as I feel my genderfluidity (esp. tied in with those things) is a feature and not a bug.

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Originally Posted by BiancaEstrella

as I feel my genderfluidity (esp. tied in with those things) is a feature and not a bug.

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Sounds like you write ad copy for Microsoft!

I wouldn't tell on the first date. But, as you go forward and decide you like her then tell before you both make commitments. I've dated a couple girls who got kicks out of it. One girl that I dated I think she was hinting her dad was a CD. I refused to guess what she was hinting at and never told her about me. Sadly I was very much in love with her. With my wife who I love dearly I told a few days after we started dating. She accepted me for whom I was. She would prefer I wasn't, but has accepted she can't change me.

If I knew what I know now:
I would tell after a few dates. I also would explain that it is something that goes on for life for most.
If she doesn't find it acceptable, please don't continue thinking you or she will change.

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Originally Posted by sometimes_miss

Sounds like you write ad copy for Microsoft!

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Microsoft would never hire me!

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Originally Posted by twelvestepemily

There's a lot of collective knowledge and experience here -- what have you guys/gals, who have successfully navigated the dating scene as a CD, done that has helped you in finding an accepting "soulmate"? Any lessons learned? What would you do differently if you had the opportunity? Any particularly useful sites/resources?

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I can tell you how my SO handled it with me and past girlfriends (I'm a GG). He was in a long-term relationship when younger, and he began exploring the CDing while in that first relationship, so there wasn't anything to tell her in the beginning. Luckily my SO's partner was accepting and my SO was not hampered in the exploration of the CDing. They broke up eventually (for reasons other than the CDing) and my SO was single for about 10 years before he met me. During the course of those ten years he established the beginnings of relationships with various GGs hoping to find someone he could commit to but there was not one GG he felt comfortable telling, and so all those relationships were short-lived (anywhere from 6 months to a year).

I knew him for 3 years before we began dating and I had fallen for him way before he fell for me. He told me at the beginning of our dating, likely because he didn't feel he had anything to lose. If I had not been OK with it, I don't think our relationship would have progressed.

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Originally Posted by twelvestepemily

My hope is that we can cobble together a list of tips might help anyone in a similar position to me who comes across this thread, but in case it helps with giving me some specific suggestions, here's a bit more about me and what I'm looking for.
- I've only dated GGs so far, but am open and curious about being with other that are anywhere on the gender spectrum (guys, girls, or anywhere in between - CDs, TSs, etc)

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The issue isn't how to explain the CDing to other CDs & TSs, right? They would have a tendency to understand and accept more readily than a GG who has not been exposed to the CDing?

So if you're looking for advice on how and when to tell a GG, I'd advise telling her once the relationship has progressed to the point where you both know that you have feelings for one another. I would not advise telling someone on the first date.

As to what to tell her, I think this all depends on what you do and how you see yourself. If you enjoy being a male who crossdresses occasionally to express a feminine side, then tell her this. If it is sexual for you, tell her this as well. If you do not see yourself as either male or female but you vary your presentation to reflect how you feel on any given day, or if you do feel you are female and you only present as a male out of convenience, tell her this as well. If you are a female who has transitioned, then obviously this will be apparent with no room for misinterpretation.

Ultimately it will be how you feel and what you choose to do with it that will influence whether a GG can see herself in a relationship with you. But whatever you do, please don't intentionally minimize what you want to do in the future, if this is not immediately apparent when you first meet the GG. Doing this can lead to problems later on.

Also, the circles you run in will influence the percentage of GGs who might be open to the CDing, i.e. urban vs rural, young-ish vs older, conservative vs. more socially liberal parts of the country, etc.