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Dating and when to let them know

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(@Anonymous)
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This has been my problem for several years.

Last GF knew about my cross-dressing and encouraged me, but things just did not work out. Now I'm back to the dating world and as scary as it can be, I always find myself in the "friends-zone" once I let them know...

I have no problems finding quality people to date. They love my male characteristic; funny, witty, fun to be around, great conversations, phenomenal personality! Over the weeks we date we talk for hours so my best to impress them. Usually I am doing just about everything right within my power. But then comes a time when I feel before things before more serious I should let them know of her...

Each person takes it differently, usually they are puzzled and shocked. From there the conversation stays the course of the topic and inquiries are made. So you like men? Are you bi? Why do you do it? The general thousand questions that quickly come to mind. At this point the mood shifts drastically. The interest level drops several notches and now I am fighting the uphill battle of my questionable sexuality.

I am doing my best to educate them of who I am. I don't understand how minutes before this conversation they were enjoying me as I am, yet as soon as I volunteer this information, although they are still speaking that same person, the interest and mood is now gone if not spoiled. The same charm I once had forever changed.

Most of my dates end as a friendship if I play my cards right. It is utterly devastating going from rejection to rejection for something that they don't understand or don't give a chance to.

So I ask, what can I do different?

  • If I don't tell them I might get further into a relationship but I must hide her...
  • If I tell her then the rejection is nearly guaranteed and but I might gain another friend.
  • Tell them up front and hope for the best? (only thing I can think of)

Anyhow, I would appreciate any feedback or thoughts.

 

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5 Replies
Posts: 172
Lady
(@holly-g)
Estimable Member     Virginia, United States of America
Joined: 9 years ago

I feel your pain Natalie. It's funny, even before I was married, I was the type who always became the great friend…maybe that says something about my inner personality and how I get along as one of the girls 😉

I didn't tell my wife until many years into our marriage. She was hurt and confused and we had the same questions you just rattled off that night. In the end she said she was more hurt that I didn't confide in her sooner about this, but my wife has become more and more accepting of alternative lifestyles as my kids have gotten into theater and we've seen even high school kids openly gay and cross dressing on stage.  I think that helped when the topic finally came up…even if the it came up because she found my heels one day 😉

I wish I had a good answer for you, but I do understand what you're saying.

Always here to listen and offer what I can.

????????

Holly

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Posts: 11
(@jessicaarcher)
Active Member     Hadley, New York, United States of America
Joined: 9 years ago

I've kinda come out to girlfriends in the past, but that was when I was a young-one.  My current single's ads are basically full disclosure, we are a package deal 🙂  Some sites offer more than the binary choices.  It just _can't_ lead to fewer potential dates, right?

I recently signed up for a semi-popular site for older folks. I think it has been on TV, but I won't mention the name. It's not one of the big 2. I haven't paid for it yet, but I instantly have lots of attention. It's a male seeking female ad using the same profile picture I do here.  I'll be paying for a month's worth next week...I'm curious as to the nature of the 20-some-odd emails.

Its not like I have any sort of "upper hand", it is an invitation to communicate with the authentically open and curious, as well as one to ignore those with negative reactions. Such an ad kinda draws all kind of attention. Its human nature to have different reactions to the unfamiliar and unexpected, and its naive for me to think otherwise.

And that doesn't make things any easier.

Hugs,

Jessica

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Posts: 20
Lady
(@dw6235)
Eminent Member     Jackson, Michigan, United States of America
Joined: 9 years ago

I always bring it up immediately now on the first dare cause I don't want to get involved emotionly again or be rejected again for who I'm and always will be and being upfront about it let's them decide to sTay involved or not I guess I take a no hold bar approach

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

Natalie, I'm so sorry you have had so many tough outcomes but that's really courageous that you are always honest with people fairly early. Holly, way to stay strong as well and Debra I like your all-in approach.

I can offer some experiences but from a bit of a different angle. Both of them speak to how hard this stuff is even when you think you have a golden opportunity.

1: I dated a cute girl who was really into me as male. I wanted so badly come out to her as Lindsay but figured that gender dysphoria would simply go away if I had a committed relationship long enough. It didn't, and one day she made a joke about doing my makeup and giving me a girl makeover. I was so shocked and nervous but played it off to calm any suspicions. Still though, we talked about doing a 'girl day' in the future where she could dress me up however she wanted and make me do girl stuff. I never had the guts to pursue this further and when something went sour in the relationship, I let it slip away. We met as friends a year later and she still found a way to joke about me looking good as a girl and I'm kicking myself that I didn't see the signs and take advantage of this. It's probable that she would have been into Lindsay but was too afraid to bring it up herself.

2: having learned from that (maybe?), I signed up for CDmeet.com and met a beautiful girl who's into crossdressers and we immediately clicked and started talking over the phone. It was completely surreal to hear her talk about liking feminine guys as if she were an 'average' girl talking about liking strong manly guys. Even so, talking about this common ground of crossdressing has proven more difficult that I thought because there are so many nuances in our preferences and desires...like, because we met on a site explicitly for women who like CD men, we expected to be totally in sync and then were disappointed that there is still so much variation and diversity in what it means to have a crossdressing relationship.

Rereading the above, I guess I'm blessed with some great opportunities I should pursue. But my main point was to say that I think this stuff is complex and difficult no matter what. We should have permission to be fully open and honest because even when we are, it still takes a lot of teamwork and communication.

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Posts: 0
Guest
(@Anonymous)
New Member
Joined: 1 second ago

2015_relationship advice: Natalie original post: 

This has been my problem for several years.

Last GF knew about my cross-dressing and encouraged me, but things just did not work out. Now I’m back to the dating world and as scary as it can be, I always find myself in the “friends-zone” once I let them know…

I have no problems finding quality people to date. They love my male characteristic; funny, witty, fun to be around, great conversations, phenomenal personality! Over the weeks we date we talk for hours so my best to impress them. Usually I am doing just about everything right within my power. But then comes a time when I feel before things before more serious I should let them know of her…

Each person takes it differently, usually they are puzzled and shocked. From there the conversation stays the course of the topic and inquiries are made. So you like men? Are you bi? Why do you do it? The general thousand questions that quickly come to mind. At this point the mood shifts drastically. The interest level drops several notches and now I am fighting the uphill battle of my questionable sexuality.

I am doing my best to educate them of who I am. I don’t understand how minutes before this conversation they were enjoying me as I am, yet as soon as I volunteer this information, although they are still speaking that same person, the interest and mood is now gone if not spoiled. The same charm I once had forever changed.

Most of my dates end as a friendship if I play my cards right. It is utterly devastating going from rejection to rejection for something that they don’t understand or don’t give a chance to.

So I ask, what can I do different?

If I don’t tell them I might get further into a relationship but I must hide her…

If I tell her then the rejection is nearly guaranteed and but I might gain another friend.

Tell them up front and hope for the best? (only thing I can think of)

Anyhow, I would appreciate any feedback or thoughts.

 

Reply

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