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Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.      Home login  
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 platypus_man
Joined: 8/29/2007
Msg: 51
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Crossdressing; tell up front, or wait? Another bad experience.Page 3 of 8    (1, 2, 3, 4, 5, 6, 7, 8)
Borrow clothes? Maybe in the beginning. When it started, I was given the clothes to wear. As I got in my early teens, I took a few of my sister's old clothes that she didn't wear anymore (snuck them out of the clothing donation bags before mom took them to the donation bins, pretty easy really). After that, mail ordering did the rest. Today's internet shopping makes buying anything pretty anonymous. Heels hurt, quirky? Try some different ones; even the same sizes will feel different from different manufacturers; worked for me.
 Gwendolyn2010
Joined: 1/22/2006
Msg: 52
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 7:19:15 AM

So I'd be friends with you but not even remotely interested in a sexual relationship.


Exactly the point I have been making. I do not choose my friends based on their sexual preferences/orientation or how they look; for lovers, it is a different matter.
 LillyAmber
Joined: 7/26/2008
Msg: 53
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 8:26:06 AM
When I was in my early 20's, a guy I use to hang with put on a dress of mine, borrowed a female friends pink hat, put on hose(with his hairy legs)wore make up, even though he had a mustache and beard. He held a pair of pumps in his hands, and complained they were hurting his feet.He did this while we walked through Wal-Mart, just to see reactions of people.
 packagedealx3
Joined: 2/4/2006
Msg: 54
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 8:36:57 AM
I'm so not reading there pages but I think if you don't tell soon enough and then the bomb is dropped, no matter how discreet you try to be about it, a woman is going to feel betrayed, period. Doesn't matter what the content of the bomb is. They wonder if they can believe anything you say to them, trust is a fragile thing.

Conversely, if you tell them too soon, they haven't figure out whether they like you and are much less willing to invite something in their life that has to be "dealt" with. I suspect that timing will always suck but might I suggest another way of bringing it up?

Maybe find a comedy club with a cross-dressing comedian. Then instead of announcing I am a cross-dresser, ask her what she thinks about it. You will get an idea of whether she has any knowledge at all, whether she will immediately go to gay in her brain and other information that will allow you to figure out how best to approach it.

If you start off with the information you provided in this post, you are not gay, you would keep a locker and rent a hotel room when you want to hang out in drag, since you say you don't go out dressed as a woman, then she knows from the beginning that you are not an STD risk and that this really will have zero impact on her life unless you find that you need oodles of time hanging this way, maybe even the more closed-minded gals could give you a chance to see how things go.
 dysfunction_junction
Joined: 7/17/2008
Msg: 55
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 8/8/2008 8:41:15 AM
4 hours in high heels is enough for me... ouch!...

haha, i can barely make it for an hour and a half in those things
 swayzin
Joined: 11/23/2007
Msg: 56
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 2:27:17 AM
great comments give them hell
 swayzin
Joined: 11/23/2007
Msg: 57
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 2:28:49 AM
i always tell up front,and i have many many lady friends i go out with,,its the best way be honest
 GeneralizingNow
Joined: 10/10/2007
Msg: 58
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 8:35:41 AM
It sucks that some people can't deal with your niche, but it IS a niche, so you know it's going to be even more difficult to find someone. I think you need to find a place where you can be who you are.

My friends would totally be okay with ANOTHER crossdresser in our midst. Our friend has no alternate name, though--he's always J. But we don't care if he's wearing a gown or a men's suit. I only wish he'd cut his hair, frankly--it's stringy. BTW, all, he's married and has a son. Totally hetero.
 ***blue***
Joined: 4/21/2008
Msg: 59
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 11:42:51 AM
I don't know but I don't think it would be an issue for me.
I just see it as a quirk and everyone has those.
To each thier own.
 indehills
Joined: 2/23/2008
Msg: 60
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 11:53:10 AM
I think it's best to be up front about ANYTHING major that might be a dealbreaker. I think most "biggies" are either going to be accepted by a potential mate or not, regardless of when you tell them.
 spitfire6844
Joined: 6/30/2007
Msg: 61
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:07:42 PM

I think it's not necessary until you get to know if it's someone you'll be intimate with.


This kind of conversation should happen up front. It is a big deal and will be something that a lot of people won't want to overlook. Waiting a few dates before dropping this bomb is manipulative, and will generate an even stronger negative response. Always be honest upfront.
 carolann0308
Joined: 12/9/2006
Msg: 62
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:09:49 PM
I just find it astounding that a self proclaimed straight male knows who Lisabeth Scott is.
 Dumpling-Girl
Joined: 7/20/2005
Msg: 63
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:14:08 PM
My opinion is that it would be best to tell on the first date (or before, if there is communication before that, on the phone or online). I think you need to find yourself an open-minded girl for it to have any chance of working. If a woman is open-minded enough to have a serious relationship with a closet cross-dresser than she will be open-minded before you even start dating.

The alternative you present is that someone gets attached to you, and then you tell them, and hopefully by this time they are so attached, they are willing to overlook this, right? Well, I think that's asking a lot from someone who isn't open-minded about this stuff. They will feel a bit bamboozled if you went a while hiding this from them. That breaks down any trust that has been built up. And can cause her to worry about what else you are capable of hiding.

I think it's just better to find someone open in the first place, then it won't be so much of a concession to deal with for them, and easier all around. Don't date someone thinking you can change someone (in this case make them more open minded about cross-dressing), it's better to find someone who's already a good match for you.

I would respect someone for being honest with me right away. If I was attracted enough to a person, and he explained that it was something he would do on his own that wouldn't interfere with our intimacy, then I might give it (dating him) a shot. I would be taken aback if he started dating me and sprung it on me, even though I am fairly open-minded about this stuff.
 Plastic Sturgeon
Joined: 12/5/2007
Msg: 64
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:22:20 PM
Do it quick and get it over with! Yay or Nay!

How about this? First time you are at one or the others place,
slip away to the washroom with your girlie threads in hand, change,
and make an appearance!

Don't forget to say " Tah Dahhhh!" As this always helps to break the tension!
 pirateheaven
Joined: 5/11/2008
Msg: 65
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 9/16/2008 12:31:42 PM
You have gotten good advice so I will give you some to lighten the mood.

Just find a woman who has the same shoe size/dress size. Ask her how would she like to have her wardrobe doubled. Then tell her the news.
 Helen0426
Joined: 6/2/2009
Msg: 66
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 2:07:52 PM

People don't think twice if you own a gun, but for some reason it's a big deal if you own a pair of pantyhose?

*laughin'*

Other way 'round for me! Panythose, fine (you won't get me in them, but if you wanna wear 'em, knock yourself out); firearms, eh, I'm not going to freak out about it as long as they're kept locked, but I'd just as soon you didn't have 'em.

 Kazzmere
Joined: 7/22/2009
Msg: 67
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 4:37:19 PM
I dated this fabulous man I met here on POF for a bit. Handsome, funny, erudite, sophisticated & generous. On our fourth date he decided to tell me the "truth" about how he made his living. What he had written on his profile wasn't true.

I did my best to not be judgmental about his chosen industry, but had he told me up front, before our first date, I would NOT have wasted our time and energy on those four dates, plus all the calls and e-mails that went on between meet ups.

I wish he had told me up front. Nice guy, just not for me.
 verygreeneyez
Joined: 3/15/2006
Msg: 68
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 6:42:20 PM
~OP~ The only problem I see with your dilemma is that you have nicer legs than me. Seriously, I'm sure it's a lot for someone to take in, especially in the beginning. BUT, I think I'd personally be more concerned with the childhood stuff than the fact you like to dress unconventionally. Good luck to ya.
 aaamm
Joined: 7/5/2009
Msg: 69
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 7:19:41 PM
Maybe I missed this, but is there a reason you don't have pics of you not crossdressing - clothing you would wear on a date? I think you have to be upfront about most non mainstream things, but you said you date in male clothing, why not have pictures of the way you would actually go out?
 Wicked_Cricket
Joined: 9/26/2009
Msg: 70
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/2/2010 7:36:08 PM
note to self: first chance u get, go thru guy's closet & drawers, check for better clothes/shoes than mine
 IgorFrankensteen
Joined: 6/29/2009
Msg: 71
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/4/2010 11:08:29 AM
I've only known one crossdresser in my life, and I know that he found both a fine relationship which still exists (they married within two years of college and are still together), and he eventually left his crossdressing days behind, AFTER he was with his wife for some time.
As far as when to tell, the only thing I can say for sure, is that if it's going to kill the relationship, it will kill it whenever you tell, so sooner is certainly more cost-effective than later. Like anything out of the ordinary, it's up to you to accept that your special attribute will narrow your available mates, just as any kind of attribute does, including birth defects, sexual orientation, addiction to tobacco, etc etc.
 Spagett!
Joined: 8/9/2009
Msg: 72
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/4/2010 11:13:01 AM

Being outside of the status quo doesn't mean you had some sort of demented childhood.

It does here! Welcome to POF!
Speaking from experience, believe me you have it easy in here.

As for the Topic at hand:
ALWAYS tell them UP FRONT.

It is lying, and a super waste of time if you do not. If the girl is going to dump you for it, better now than later. Do you want a relationship with someone who does not accept you? This is not about the clothes, it is about your lifestyle. ALWAYS make sure your lifestyles are compatible, that is the first and foremost thing that will kill a budding relationship. As it should.

PS: PERSONAL PREFERENCE to the bigoted posts.
 Helen0426
Joined: 6/2/2009
Msg: 73
Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/4/2010 2:47:28 PM
You may be right, Spagett! (heh - cute), that it should be right up-front. I'd be okay with hearing about it later, but then, that's probably in large part because I'm okay with it!

Editing to add, the original poster - over two years ago, so I doubt he's still reading - did refer to having lingering problems due to childhood abuse, in the opening post. Evidently this was okay with the woman he was dating but the cross-dressing was not. I believe the point was that this constituted a pretty backwards way for her to look at the two things... and I agree.
 Spagett!
Joined: 8/9/2009
Msg: 74
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/6/2010 11:29:31 AM

... it's no big deal if their partner isn't into it.

If it was not a big deal, then why the thread?


For some it's a fetish or something...

Exactly, and a rather "taboo" one at this point. Lifestyle or not, it is something that should be brought up, up front. Unless one enjoys being a liar, or do you not enjoy wearing womens clothing?


I would be kinda funny if every woman you met for a date said: "Hi, nice to meet you, my name is Molly and I have a big foot fetish."

Comparing apples to oranges at this point. A foot fetish is not "taboo", a man dressing as a woman is. Until that changes, it is inconsiderate to keep such a thing "secret".

FURTHERMORE, why date someone if they are not privy to your special stuff? That is a part of you, fetish or lifestyle, hiding it from them is a disrespect to yourself, and to them. Take charge of yourself, be proud of who you are, don't hide.


Some of those things I would rather know down the road when I am more comfortable with the person, not in the awkward first date scenario.

See, I like to know if the person I am dating is compatible with me or not. I guess to each their own...
 Spagett!
Joined: 8/9/2009
Msg: 75
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Crossdressing; tell up front, or wait? Another bad experience.
Posted: 1/6/2010 12:03:54 PM

I don't tell people how much money I have in the bank account on a first date. That doesn't make me a liar.

You misunderstand. You, as a person, enjoy dressing as a woman. Right?

So when you go on a date, and are talking about you, as a person. If you omit that data, then you are not telling the whole truth, are you? Money in the bank is not a "red flag", you are trying to skirt (heh) the issue. You know damn well that there IS a BIG difference between everything you have tried to compare this to.

I am proud of my lifestyle, and I tell the gals BEFORE ANY date. It is only fair to them, not to mention myself. Why the hell would I want to go through "dating" only to have it blow up at the end because of my underwear? Why would you want to date a girl who was not "into you" (as a person)? If they do not know about your clothing habits, then they do not know you.
Show ALL Forums  > Dating and Love Advice  > Crossdressing; tell up front, or wait? Another bad experience.