Okay so he wears a dress... Now what? Let me get to the start of the story and you can tell me, was my advice good?
So she has met this wonderful guy. Well more than met, she knew what she wanted and headed straight for him. She would tell you that herself. That is how she is. Although we seldom talk and never have 'hung out' I have become her confidante when it comes to relationship issues. She has made a lot of mistakes in moving too quickly with men, getting involved emotionally and physically from the start and she wants to change. I admire her for that. She says she comes to me because I have the standards that she wants to have. (and yes, we have worked on her self-esteem issues). Things seemed to be going well for her, he is a shyer type of guy and l think he finds her intriguing yet, he wants to take it slow. I assure her this is good for her. Get to know the heart of the man, who he is and let him get to know her.
Recently she found me running an errand and said she really needed to talk to me. She recently found out that the man of her dreams is a cross-dresser. She asked me, was that "weird?" Hey, Southeastern Oklahoma - what can I tell you?
"Should that bother me?" I told her the question wasn't what I thought of it, or anyone else for that matter, but what did she think of it? I listened and she talked freely of the thoughts that had been running through her mind since he shared this vital information.
I pointed out first and foremost, given his position in the community he has shown a lot of trust in telling her this. He goes to larger cities and unrecognized places far from here when dressing in female attire. I mention this to her because she has a tendency to "like to share secrets" and this is one that could destroy a man and a reputation in this area.
I pointed out that I had known some cross dressers and their clothes and make-up were beautiful - maybe you can borrow his clothes, I joked. And she seems to calm down some and agree that it is something they need to talk about together and something she has to answer within herself. Me personally? Like I told her, if your happy with it and he's happy with it who is anyone else to judge?
But yesterday when I saw her I asked how things were going. It seems a problem might have arisen. She told me she jokingly told him as long as he stayed a man she was sure she could accept his occassionally dressing as a female. To which he told her that is what he is seeing a therapist about.
I asked what does that mean and she said that she thinks he is thinking about having the operation but she didn't want to question him too much or push. I told her that is the one thing I would have pushed on. You can look at a man who wants to dress like a woman sometimes as a 'quirk' or however you want to look at it, and if both people are comfortable with it, it doesn't really affect a relationship. But if your boyfriend is having thoughts about becoming a female - now that could have some serious repercussions. I don't want her to get hurt and I told her that. I told her she needs to know where he stands and she has a right to know. I pointed out this is probably part of the reason he has held back on her thus far, he is unsure where he is at. So they need to talk it out, she can't just ignore it and hope it will go away.
I don't want to interfere with anyone's life but she has asked me to be her friend and confidante and as that, I really think she needs to step back and find out where he is going and how he really feels before getting more involved. Or should I just stay out of it? What do you think?
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oppositeview
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May 25 @ 2:32PM
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You should definitely say what you think. IF she's asking you for your opinion. She seemed a little overwhelmed by the first 'secret'. She may deem this new development as part of the overall package. It's not. One's changing clothes, the other's changing your life. You were right in enlightening her, both times.
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sciurusniger
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May 25 @ 2:40PM
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With all of this, my advice to her would simply be to continue to see this man as a friend and nothing more.
For if he is truly feeling ambivalent about his sexuality, he needs someone in whom he can confide, with whom he can share his feelings freely without fear of breaking something (i.e. a committed "traditional" relationship) more than he needs to be in a "traditional" relationship.
If she cannot handle being "just friends", then I honestly think she should break things off with him. Too much potential for both of them to end up badly hurt otherwise.
YMMV
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JimNastics
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May 25 @ 3:58PM
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I really can't believe I am saying this. But, I actually agree with sciu. 
So, maybe I haven't thought about this enough. 
To be honest, I really don't want to think about it anymore. 
So, I'll go with what sciu says. Honestly, it sounds like good advice anyway.
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salsapiccante
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Aug 4 @ 1:55PM
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As her confidente she has high regards for your opinion and if you wont hold anything back about how you feel then tell her as you think it be open about what you don't like about this relation and what she should do even if it means telling her to break up with this guy.On the other hand see her level of attachment to this guy and see if you can get some deep-seated confessions from her before you give your opinion.A little more details would go a long way to help you have an idea on what opinion to give!
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