Harder than I remember...and something interesting, too, you should know, maybe try

[sometimes_miss]

Well, I've been divorced now for 15 years. For most of that time, I've failed miserably at trying to date; being up front about my crossdressing, I always thought that was the 800 pound gorilla keeping me from finding someone new. Yet....I've had a few dates since I put my crossdressing on hold, and have found: Most women are batsh!t nuts. I'd forgotten all about this. The ones that simply won't shut up. The ones who believe in astrology to the point they call in sick and won't even leave the house if 'the stars' say it will be a dangerous day. The diet nuts, who tell me I'm going to die from eating cooked red meat while they eat raw fish. The lady with 12 cats (nuff said). One who truly was psychotic, and luckily was currently on her meds (but she sometimes stops taking them when she needs a 'vacation').

Now the important item. In discussion, I told two about crossdressing; more specific, that I USED TO be a crossdresser. After a bit of discussion, it wasn't seeming to be a problem. Of course, after a couple of dates, their own lunacy seemed to still be way over the top to me, but we wound up not pursuing any further relationship for other reasons. But I found it interesting that the 'USED TO BE A CROSSDRESSER' confession didn't drive them away instantly like telling women that I WAS currently a crossdresser. This brings to the forefront that it may be a way to ease into it when you come out to someone....tell them you USED to do it, and see how they respond from there. For whatever reason, there seems to be a big difference in how women respond to this. I don't know what the reaction would be should I ever admit to having a relapse; I'm not sure I would want to chance it, should I wind up finding someone I like so much that to lose her would really hurt. I haven't reached that point just yet.
But I needed to let everyone here know what's happened so far.

[Gretchen_To_Be]

So, what would you do if you found someone you felt strongly about, and when you revealed that you "used to be" a crossdresser, she reacted favorably and wanted enthusiastically for you to resume? Would you indulge her?

[Kelly DeWinter]

I've always subscribed to the philosophy that everyone is a little bit cracked , some more so then others. This includes myself. So all those situations you describe are part of life. Can you imagine what they say when they talk about a date with you ? What one person finds normal another finds abnormal.

[sometimes_miss]

So, what would you do if you found someone you felt strongly about, and when you revealed that you "used to be" a crossdresser, she reacted favorably and wanted enthusiastically for you to resume? Would you indulge her?

Considering the likelyhood of that happening, it's not something I'm going to have to worry about. Nice fantasy, though, for a moment or two. But dreaming about something like that was one of the things that kept me hoping for that to happen for the last 15 years, so I'm not going to repeat that mistake.

[Chickhe]

That may be good angle as long as you don't make it sound negative like its buried too deep in the past...maybe add that someday you might take it up again and show her. I bet the reason telling them you are a CDer now doesn't work as well is because it is presented like it is the major issue in your life (too much information for her)...something she might have to deal with when all she really wants is to make friends and have a superficial relationship at first... It is probably a good strategy to leave some mystery and personally, I would never explain it, if I were to go through the process, I would just show them and make it fun for them.

About the crazy ones...there is a reason they are single. My friend who got divorced, said everyone has baggage and you need to accept that...

[GaleWarning]

I had to laugh ....
During my internet dating phase I met 12 women face to face after chatting on-line.
Some were truly weird ... like the cutter!
One was so much like my ex it scared the h*** out of me!
Only one seemed sane enough to meet a second time.
Turned out we both had baggage.

I've been seriously single for at least three years now. It's hard enough dealing just with myself!

[Beverley Sims]

I tried this ploy once to gain the confidence of a woman.
She was a medium into astrology and crystals but crossdressing was something strange as far as she was concerned.
She thought I was possessed by aliens and we should see a psychic friend of hers to drive the demons away.
That is when I realised if I pursued this line of cure I would indeed be weird and poorer from the exercise.

[Kate Simmons]

It's hard to find someone without a lot of drama, issues or baggage these days. In my case, due to my empathic abilities, I am a medium, so no woman could get one up on me with that one Bev.I did tell my GF that, however, along with the fact I like to dress early on and she said: "So, what?" as she likes me for me and when we are together, we are the center of each other's attention. I actually found this gem of a lady when I stopped looking so hard.

[Babette]

Most women are batsh!t nuts.

Wow, this really gave me good belly laugh! Sorry Sometimes Miss, I'm not picking on you. Your expression really tickled my funny bone.

I remember an old line that went like this, "The whole world is crazy except for you and me, and I sometimes wonder about you."

There are over 20,000 members of this forum that like to do something special - like cross dress . I wonder if there are women out there who think we are nuts - well not me of course (insert sarcasm).

Sometimes Miss, I really think I understand how you feel. Across life's pathway, we sometimes encounter some eclectic spirits.

Babette

[Lynn Marie]

I've actually been a lot more successful since I stopped looking. I'm quite happy living alone. I have friends many of whom are crossdressers. I've met my latest lady friend at an LGBT club that I hang out at on Fridays. You can see her picture on my Flickr site! Gorgeous with just a few bad habits that I can ignore because I don't have to live with her. I just visit.

[Deedee Skyblue]

In the early 80s, I had one date with a woman who promised to teach me how to fly if I taught her how to play racquetball. (Fly as in magic; she claimed to be a witch.) Unfortunately, she was so involved in a political campaign that she had difficulty making time for anything else. (or that's what she told me to let me down easy...). Have to say, I was very disappointed that I didn't get the chance to learn to fly.

Deedee :still grounded:

[paper_clip]

I told my significant other about my crossdressing habits about three weeks after I started dating her. One of the hardest things I've ever done, but it got things out in the open right away and led to what has become the best and most intimate relationships I've ever had.

[Janet Bern]

my suggestion is to get to know the person first and let her get to know you.
Drop a few hints after a few months and see if she picks up on it.
You never know... she may be ok with it

[BarbaraVa]

I got call fooling around on the one person that always accepted me unconditionally. I was a complete moron and it took me a long time to realize it. In our time apart I had many opportunities with other women, but none of them were without some sort of issue. I told a couple of them about my crossdressing if I thought there may be a chance at something, but in the end I realized the one person I should be with was the one I screwed up on. She forgave me, we got back together and that's the way it's been for the past 10 years now... It's been over 30 years that we've known each other.

[ttenneb]

My friend, said everyone has baggage and you need to accept that.

[docrobbysherry]

Lexi, I sympathize with u! I've also been divorced about 15 years. And, occasionally got involved in the internet dating scene. I'm older and married a crazy. So, I weeded them out before meeting them. My problem is many really aren't open for to a relationship. Unless it's on their terms. And others? Bored me to tears!

I did meet one that was attractive, sexy, liked me, and we went on a number of dates before I knew it wouldn't work. I told her about my dressing. After hearing her repeat, "I don't know what to say", a hundred times over the next hour, I bid her goodbye. And, haven't dated since!

[Stephanie47]

Sounds as if I will remain happily married to my wife of forty-two years. Time may be too short to find someone else who tolerates my cross dressing. I told my kids if my wife passes away I'll get a dog. They have been pestering me to get a dog for a long time.